WO2020149716A1

WO2020149716A1 - Compound and organic light emitting diode comprising same

Info

Publication number: WO2020149716A1
Application number: PCT/KR2020/000947
Authority: WO
Inventors: 강경준; 홍완표; 금수정; 김경희
Original assignee: 주식회사 엘지화학
Priority date: 2019-01-18
Filing date: 2020-01-20
Publication date: 2020-07-23
Also published as: CN112888695A; KR20200090137A; KR102353148B1; CN112888695B

Abstract

The present specification relates to a compound represented by chemical formula 1 and an organic light emitting diode comprising same.

Description

Compound and organic light emitting device comprising same

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0006918 filed with the Korean Intellectual Property Office on January 18, 2019, the entire contents of which are incorporated herein.

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it will shine.

The development of new materials for such organic light-emitting devices continues to be required.

[Patent Document] WO2017-018326 A1

This specification is intended to provide a compound and an organic light emitting device comprising the same.

The present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

A1 to A3 are the same as or different from each other, and each independently an substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,

X is B or N,

Y is N(R11), Z is O; S; Or N(R12),

Y is O; S; Or N(R11), Z is N(R12),

R1 is a substituted or unsubstituted aryl group,

R2 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

R11 is -(L11)n11-Ar1,

R12 is -(L12)n12-Ar2,

L11 and L12 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar1 and Ar2 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n11 and n12 are the same as or different from each other, and each independently 1 or 2,

When n11 is 2, L11 is the same as or different from each other,

When n12 is 2, L12 is the same as or different from each other.

In addition, the present specification is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1 do.

The compound according to the exemplary embodiment of the present specification is used in an organic light emitting device, so that a driving voltage of the organic light emitting device can be lowered and light efficiency can be improved. In addition, the lifespan characteristics of the small intestine can be improved by the thermal stability of the compound.

1 to 3 show an example of an organic light emitting device according to an exemplary embodiment of the present specification.

Figure 4 shows the luminous efficiency (Example 14) according to the doping concentration of the compound A-2 according to an exemplary embodiment of the present specification.

5 shows the luminous efficiency (Comparative Example 10) according to the doping concentration of Comparative Compound X-7.

[Description of codes]

101: substrate

102: anode

103: hole injection layer

104: hole transport layer

105: electron blocking layer

106: emitting layer

107: hole blocking layer

108: electron transport layer

109: electron injection layer

110: cathode

Hereinafter, the present specification will be described in more detail.

The compound represented by Chemical Formula 1 has a structure in which a polycyclic ring is condensed, and the A1 ring and the A2 ring are connected by carbon (bridge alkyl site). By connecting the two rings, it is possible to lower the overall fluidity of the structure and obtain a narrow half-width light emission wavelength. In addition, by introducing various substituents such as an alkyl group and an aryl group at the bridge alkyl site, the emission wavelength can be adjusted. In addition, the polycyclic structure is excellent in stability, and when used as a dopant in the light emitting layer of the organic light emitting device has long life and high efficiency characteristics.

By linking one or more aryl groups to the bridge alkyl site, the bulk of the three-dimensional structure of the molecule is bulky compared to the structure in which only the alkyl group is connected (bulky). It is possible to increase, and the interaction between the host and the dopant is reduced, thereby improving the life of the device.

Examples of the substituent in this specification are described below, but are not limited thereto.

In this specification,

Means the site to be connected.

In the present specification, Cn refers to n carbon atoms.

In the present specification, Cn-Cm refers to n to m carbon atoms.

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

The term "substituted or unsubstituted" in this specification is deuterium; Halogen group; Nitrile group; Alkyl groups; Alkoxy groups; Cycloalkyl group; Amine group; Silyl group; Aryl group; And one or two or more substituents selected from the group consisting of heterocyclic groups, or substituted with two or more substituents among the above-described substituents, or having no substituents.

In one embodiment of the present specification, the term "substituted or unsubstituted" is deuterium; Halogen group; C1-C10 alkyl group; C1-C10alkoxy group; C3-C30 cycloalkyl group; Amine group; Silyl group; C6-C30Aryl group; And N, O, or substituted with one or more substituents selected from the group consisting of C2-C30 heterocyclic group containing S or. It means that two or more groups selected from the above group are substituted with linked substituents or have no substituents.

In one embodiment of the present specification, the term "substituted or unsubstituted" is deuterium; Halogen group; C1-C10 alkyl group; Amine group; Silyl group; C6-C30Aryl group; And N, O, or substituted with one or more substituents selected from the group consisting of C2-C30 heterocyclic group containing S or. It means that two or more groups selected from the above group are substituted with linked substituents or have no substituents.

In the present specification, two or more substituents are connected means that hydrogen of one substituent is connected to another substituent. For example, an isopropyl group and a phenyl group are connected

or

It can be a substituent of.

In the present specification, (substituent 1)-(substituent 2)-(substituent 3) is not only continuously connected, but also (substituent 1) (substituent 2) and (substituent 3) are connected Includes connections. For example, two phenyl groups and isopropyl groups are connected

or

It can be a substituent of. The same applies to those above which four or more substituents are connected.

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

In the present specification, the alkyl group may be straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50, more preferably 1 to 30. Specific examples are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentyl Methyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, iso Hexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and more preferably 3 to 30 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3 ,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.

In the present specification, the haloalkyl group may be a straight chain or a branched chain, and the hydrogen of the aforementioned alkyl group is substituted with one or two or more halogen groups. Carbon number is not particularly limited, but is 1 to 30; 1 to 20; 1 to 10; Or it is preferably 1 to 5. The description of the alkyl group described above may be applied to the alkyl group. Specific examples of haloalkyl groups include, but are not limited to, fluoromethyl groups, difluoromethyl groups, trifluoromethyl groups, chloromethyl groups, dichloromethyl groups, trichloromethyl groups, bromomethyl groups, dibromomethyl groups, tribromomethyl groups, and the like. Does not work.

In the present specification, the silyl group includes Si and the Si atom is a substituent directly connected as a radical, and is represented by -SiR ₂₀₁ R ₂₀₂ R ₂₀₃ , R ₂₀₁ to R ₂₀₃ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Alkyl groups; Alkenyl group; Alkoxy groups; Cycloalkyl group; 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. It is not limited.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 50 carbon atoms, more preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, and the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is 10-50 carbon atoms, and 10-30 is more preferable. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, but is not limited thereto.

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

When the fluorenyl group is substituted, the substituent of carbon 9 may form a ring to form a spiro structure. Spirobifluorenyl group, and the like, but is not limited thereto.

In the present specification, the heteroaryl group is a heteroatom containing at least one of N, O, S, Si, and Se, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms, and more preferably 2 to 30 carbon atoms. Do. Examples of the heteroaryl group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, and acry Dean group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, phthalazine, pteridine group, pyrido pyrimidine group, pyridodo pyrimidine group, pyridodo pyridine group pyrazine), pyrazino pyrazine, isoquinoline, indole, pyrido indole, indo pyrimidine, carbazole, benzoxazole, benzimidazole , Benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, dibenzofuran group, phenanthroline, thiazolyl group, isooxazolyl group, oxadiazolyl group and Thiadiazolyl groups, and the like, but are not limited to these.

In the present specification, the amine group may be represented by the formula of -NR ₃₀₁ R ₃₀₂ , wherein R ₃₀₁ and R ₃₀₂ are each hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heterocyclic group. The amine group is an alkylamine group; Arylalkylamine groups; Arylamine group; Aryl heteroarylamine group; Alkyl heteroarylamine groups; And a heteroarylamine group, and more specifically, a dimethylamine group; Diphenylamine group; And the like, but is not limited to these.

In the present specification, the arylamine group means a group in which the nitrogen atom of the amine is substituted with an aryl group. Examples of the arylamine group include a substituted or unsubstituted monoarylamine group; Or a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. An arylamine group including the two or more aryl groups is a monocyclic aryl group; Or it may contain a polycyclic aryl group, or may include a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, and the like. no.

In this specification, a heteroarylamine group means a group in which the nitrogen atom of the amine is substituted with a heteroaryl group. The heteroarylamine group is, for example, a substituted or unsubstituted monoheteroarylamine group; Or it may be a substituted or unsubstituted diheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The heteroarylamine group including the two or more heteroaryl groups is a monocyclic heteroaryl group; Or it may include a polycyclic heteroaryl group, or may include a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.

In the present specification, the aryl heteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group.

In the present specification, the aralkylamine group means an amine group substituted with an aryl group or an alkyl group.

In the present specification, the description of the aforementioned alkyl group may be applied to the alkyl group in the aralkylamine group and the alkylaryl group.

In the present specification, the aryl group in the aryl heteroarylamine group, the aralkylamine group, and the arylamine group may be applied to the aryl group described above.

In the present specification, the description of the heteroaryl group described above may be applied to the heteroaryl group in the arylheteroarylamine group.

In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. These may be applied to the description of the aryl group described above, except that each is a divalent group.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. These may be applied to the description of the heteroaryl group described above, except that each is a divalent group.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. Can. For example, two substituents substituted in the ortho position on the benzene ring and two 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, "ring" is a substituted or unsubstituted hydrocarbon ring; Or substituted or unsubstituted heterocyclic ring.

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

In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group, except that it is not monovalent.

In the present specification, the heterocycle is a non-carbon atom, and contains one or more heteroatoms. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, may be aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the heteroaryl group except for non-monovalent.

In the present specification, the adamantyl group (adamantly group) is a type of cycloalkyl group, and the cyclohexane ring is condensed in a bridge form. In adamantane (C ₁₀ H ₁₆ ), one hydrogen is connected to the other linker,

or

It can be displayed as.

Hereinafter, the compound represented by Chemical Formula 1 will be described in detail.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently an substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently substituted or unsubstituted C6-C30 aromatic hydrocarbon ring; Or a substituted or unsubstituted C2-C30 aromatic heterocycle.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; Or a substituted or unsubstituted C2-C20 aromatic heterocycle.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tricyclic aromatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic to tricyclic aromatic heterocycle.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to bicyclic aromatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic to bicyclic aromatic heterocycle.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aromatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic aromatic heterocycle.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to bicyclic aromatic hydrocarbon ring.

In one embodiment of the present specification, A1 to A3 are the same or different from each other, and each independently a substituted or unsubstituted benzene ring.

In one embodiment of the present specification, A1 to A3 are benzene rings.

In one embodiment of the present specification, A1 to A3 may be substituted or unsubstituted by Q.

In one embodiment of the present specification, Q is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Q is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Q is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C1-C20 alkyl group; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted C1-C20 amine group; A substituted or unsubstituted C6-C60 arylamine group; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heterocyclic group.

In one embodiment of the present specification, Q is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C1-C10 alkoxy group; A substituted or unsubstituted C1-C20 amine group; A substituted or unsubstituted C6-C40 arylamine group; A substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted C2-C20 heterocyclic group.

In one embodiment of the present specification, Q is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C1-C10 alkoxy group; A substituted or unsubstituted C6-C40 arylamine group; Or a substituted or unsubstituted C6-C20 aryl group.

In one embodiment of the present specification, when Q is a substituted aryl group, deuterium; C1-C10 alkyl group; C1-C5 alkyl group; Methyl group; Or it may be substituted with a t-butyl group.

In one embodiment of the present specification, when Q is a substituted alkoxy group, a halogen group; More preferably, it may be substituted with fluorine.

In one embodiment of the present specification, Q is hydrogen; heavy hydrogen; Fluorine; Methyl group; t-butyl group; -OCF ₃ ; Diphenylamine group; An amine group substituted with a phenyl group unsubstituted or substituted with deuterium or t-butyl group; Or carbazole.

In one embodiment of the present specification, X is B or N.

In one embodiment of the present specification, X is B.

In one embodiment of the present specification, R1 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R1 is a substituted or unsubstituted C6-C30 aryl group.

In one embodiment of the present specification, R1 is a substituted or unsubstituted C6-C20 aryl group.

In one embodiment of the present specification, when R1 is a substituted aryl group, deuterium; C1-C10 alkyl group; Or it may be substituted with a C1-C5 alkyl group.

In one embodiment of the present specification, R1 is a C6-C20 aryl group unsubstituted or substituted with a deuterium or alkyl group.

In one embodiment of the present specification, R1 is a C6-C20 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium or C1-C5 alkyl groups or two or more groups selected from the group.

In one embodiment of the present specification, R1 is a C6-C20 aryl group unsubstituted or substituted with deuterium or a C1-C5 alkyl group.

In one embodiment of the present specification, R1 is a phenyl group unsubstituted or substituted with a deuterium or methyl group.

In one embodiment of the present specification, R2 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R2 is a substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted C6-C30 aryl group.

In one embodiment of the present specification, R2 is a substituted or unsubstituted C1-C5 alkyl group; Or a substituted or unsubstituted C6-C20 aryl group.

In one embodiment of the present specification, when R2 is a substituted alkyl group, it may be substituted with deuterium.

In one embodiment of the present specification, when R2 is a substituted aryl group, deuterium; C1-C10 alkyl group; Or it may be substituted with a C1-C5 alkyl group.

In one embodiment of the present specification, R2 is a substituted or unsubstituted C1-C5 alkyl group; Or a C6-C20 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium or C1-C5 alkyl groups or two or more groups selected from the group.

In one embodiment of the present specification, R2 is a substituted or unsubstituted C1-C5 alkyl group; Or a C6-C20 aryl group unsubstituted or substituted with deuterium or a C1-C5 alkyl group.

In one embodiment of the present specification, R2 is a methyl group; Or a phenyl group unsubstituted or substituted with deuterium or methyl groups.

In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently a substituted or unsubstituted C6-C30 aryl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently substituted with one or more substituents selected from the group consisting of deuterium or C1-C5 alkyl groups or two or more groups selected from the group, or It is an unsubstituted C6-C20 aryl group.

In one embodiment of the present specification, Y is O; S; Or N(R11).

In one embodiment of the present specification, Z is O; S; Or N(R12).

In one embodiment of the present specification, Y is N(R11).

In one embodiment of the present specification, Y is N(R11), Z is O; S; Or N(R12).

In one embodiment of the present specification, Z is N(R12), Y is O; S; Or N(R11).

In one embodiment of the present specification, R11 is -(L11)n11-Ar1.

In one embodiment of the present specification, R12 is -(L12)n12-Ar2.

In one embodiment of the present specification, L11 and L12 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.

In one embodiment of the present specification, L11 and L12 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6-C30 arylene group; Or a substituted or unsubstituted C2-C30 divalent heterocyclic group.

In one embodiment of the present specification, L11 and L12 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6-C20 arylene group; Or a substituted or unsubstituted C2-C20 divalent heterocyclic group.

In one embodiment of the present specification, L11 and L12 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted C6-C20 arylene group.

In one embodiment of the present specification, L11 and L12 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, when L11 or L12 is a substituted arylene group, an alkyl group; C1-C10 alkyl group; C1-C5 alkyl group; Heterocyclic group; C6-C30 heterocyclic group; Or it may be substituted with a C6-C20 heterocyclic group.

In one embodiment of the present specification, when L11 or L12 is a substituted arylene group, deuterium; And one or more substituents selected from the group consisting of alkyl groups or two or more groups selected from the group. More preferably, the arylene group of L1 or L2 is deuterium; And it may be substituted with one or more substituents selected from the group consisting of C1-C5 alkyl group or two or more groups selected from the group.

In one embodiment of the present specification, when L11 or L12 is a substituted divalent heterocyclic group, an alkyl group; C1-C10 alkyl group; C1-C5 alkyl group; Aryl group; C6-C30Aryl group; Or it may be substituted with an aryl group of C6-C20.

In one embodiment of the present specification, L11 and L12 are the same as or different from each other, and each independently a direct bond; A C6-C20 arylene group unsubstituted or substituted with a C1-C5 alkyl group or a C2-C20 heterocyclic group; Or a C2-C20 divalent heterocyclic group unsubstituted or substituted with a C1-C5 alkyl group or a C6-C20 aryl group.

In one embodiment of the present specification, L11 and L12 are the same as or different from each other, and each independently a direct bond; Or a C6-C20 arylene group unsubstituted or substituted with a C1-C5 alkyl group.

In one embodiment of the present specification, L11 and L12 are the same as or different from each other, and each independently a direct bond; A phenylene group unsubstituted or substituted with a methyl group or a t-butyl group; Naphthylene group; A fluorenylene group substituted with a methyl group; Terphenylene group; A divalent pyridine group unsubstituted or substituted with a phenyl group; Divalent dibenzofuran group; Or a divalent dibenzothiophene group.

In one embodiment of the present specification, L11 and L12 are the same as or different from each other, and each independently a direct bond; Or a phenylene group unsubstituted or substituted with a methyl group or a t-butyl group.

In one embodiment of the present specification, n11 is 1 or 2.

In one embodiment of the present specification, n12 is 1 or 2.

In one embodiment of the present specification, n11 is 1.

In one embodiment of the present specification, n12 is 1.

In one embodiment of the present specification, when n11 is 2, L11 is the same or different from each other, and when n12 is 2, L12 is the same or different from each other.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; A substituted or unsubstituted C1-C20 alkyl group; A substituted or unsubstituted C3-C30 cycloalkyl group; A substituted or unsubstituted C1-C20 haloalkyl group; A substituted or unsubstituted C1-C60 silyl group; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heterocyclic group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C3-C20 cycloalkyl group; A substituted or unsubstituted C1-C10 haloalkyl group; A substituted or unsubstituted C1-C40 silyl group; A substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted C2-C20 heterocyclic group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C3-C30 cycloalkyl group; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heterocyclic group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C3-C20 cycloalkyl group; A substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted C2-C20 heterocyclic group.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted alkyl group, deuterium; Or it may be substituted with a halogen group.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted silyl group, an alkyl group; C1-C10 alkyl group; C1-C5 alkyl group; Methyl group; Aryl group; C6-C30Aryl group; C6-C20Aryl group; Or it may be substituted with a phenyl group.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted aryl group, deuterium; Halogen group; Alkyl groups; An alkyl group substituted with deuterium; Haloalkyl group; Silyl group; And one or more substituents selected from the group consisting of heterocyclic groups or two or more groups selected from the group.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted aryl group, deuterium; Halogen group; Alkyl groups; An alkyl group substituted with deuterium; Haloalkyl group; A silyl group substituted with an alkyl group; Or it may be substituted with a heterocyclic group.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted aryl group, deuterium; Halogen group; C1-C10 alkyl group; A C1-C10 alkyl group substituted with deuterium; C1-C10 haloalkyl group; A silyl group substituted with a C1-C10 alkyl group; Or it may be substituted with a heterocyclic group of C2-C30.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted aryl group, deuterium; Halogen group; C1-C5 alkyl group; A C1-C5 alkyl group substituted with deuterium; C1-C5 haloalkyl group; A silyl group substituted with an alkyl group of C1-C5; And C2-C20 heterocyclic groups, or one or more substituents selected from the group, or two or more groups selected from the group, may be substituted with linked substituents.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted aryl group, deuterium; Halogen group; C1-C5 alkyl group; A C1-C5 alkyl group substituted with deuterium; C1-C5 haloalkyl group; Or it may be substituted with a C2-C20 heterocyclic group.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted aryl group, deuterium; And C1-C5 alkyl group may be substituted with one or more substituents selected from the group consisting of two or more substituents.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted aryl group, deuterium; C1-C5 alkyl group; Or it may be substituted with a C1-C5 alkyl group substituted with deuterium.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted aryl group, deuterium; Halogen group; Methyl group; Ethyl group; Propyl group; t-butyl group; CD ₃ ; CF ₃ ; Pyridine group; Pyrimidine group; Dibenzofuran group; Dibenzothiophene group; Or it may be substituted with a carbazole group.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted aryl group, deuterium; A methyl group unsubstituted or substituted with deuterium; It may be substituted with a t-butyl group.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted heterocyclic group, deuterium; Halogen group; Alkyl groups; An alkyl group substituted with deuterium; Haloalkyl group; Or it may be substituted with an aryl group.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted heterocyclic group, deuterium; Halogen group; C1-C10 alkyl group; A C1-C10 alkyl group substituted with deuterium; C1-C10 haloalkyl group; Or it may be substituted with an aryl group of C6-C30.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted heterocyclic group, deuterium; Halogen group; C1-C5 alkyl group; A C1-C5 alkyl group substituted with deuterium; C1-C5 haloalkyl group; And a C6-C20 aryl group, or one or more substituents selected from the group or two or more groups selected from the group may be substituted with linked substituents.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted heterocyclic group, deuterium; Halogen group; C1-C5 alkyl group; A C1-C5 alkyl group substituted with deuterium; C1-C5 haloalkyl group; Or it may be substituted with an aryl group of C6-C20.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted heterocyclic group, deuterium; Halogen group; Methyl group; Ethyl group; Propyl group; t-butyl group; CD ₃ ; CF ₃ ; Phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Or it may be substituted with a fluorenyl group.

In one embodiment of the present specification, when Ar1 or Ar2 is a substituted heterocyclic group, deuterium; A methyl group unsubstituted or substituted with deuterium; It may be substituted with a t-butyl group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a C3-C20 cycloalkyl group; A substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted C2-C20 heterocyclic group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a C3-C30 cycloalkyl group; In the group consisting of deuterium, halogen groups, C1-C5 alkyl groups, C1-C5 alkyl groups substituted with deuterium, C1-C5 haloalkyl groups, C1-C5 alkyl group-substituted silyl groups, and C2-C20 heterocyclic groups. A C6-C20 aryl group, which is unsubstituted or substituted with one or more substituents selected or two or more groups selected from the group; Or in the group consisting of deuterium, halogen group, C1-C5 alkyl group, C1-C5 alkyl group substituted with deuterium, C1-C5 haloalkyl group, C1-C5 alkyl group-substituted silyl group, and C6-C20 aryl group. It is a C2-C20 heterocyclic group unsubstituted or substituted with one or more substituents selected or two or more groups selected from the group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a C3-C30 cycloalkyl group; In the group consisting of deuterium, halogen groups, C1-C5 alkyl groups, C1-C5 alkyl groups substituted with deuterium, C1-C5 haloalkyl groups, C1-C5 alkyl group-substituted silyl groups, and C2-C20 heterocyclic groups. A C6-C20 aryl group, which is unsubstituted or substituted with one or more substituents selected or two or more groups selected from the group; Or C2 substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, an alkyl group of C1-C5, an alkyl group of C1-C5 substituted with deuterium, and an aryl group of C6-C20, or two or more groups selected from the group. -C20 heterocyclic group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently substituted or substituted with one or more substituents selected from the group consisting of deuterium and C1-C5 alkyl groups or two or more groups selected from the group. A substituted C6-C20 aryl group; Or a C2-C20 heterocyclic group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an adamantyl group; A phenyl group unsubstituted or substituted with deuterium, fluoro, methyl, t-butyl, trifluoromethyl, trimethylsilyl or pyridine groups; A biphenyl group unsubstituted or substituted with deuterium, fluoro, t-butyl or trifluoromethyl; A terphenyl group unsubstituted or substituted with a deuterium or trifluoromethyl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group; A methyl group, a methyl group substituted with deuterium, or a pyridine group unsubstituted or substituted with a phenyl group; a dibenzofuran group unsubstituted or substituted with a t-butyl group; Or a dibenzothiophene group unsubstituted or substituted with a t-butyl group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium, a methyl group, or a t-butyl group; A biphenyl group unsubstituted or substituted with deuterium or t-butyl group; Or dibenzofuran group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently deuterium; Halogen group; A C1-C10 alkyl group unsubstituted or substituted with deuterium; C3-C20 cycloalkyl group; CF ₃ ; Trimethylsilyl group; C6-C20 aryl group unsubstituted or substituted with deuterium or C1-C10 alkyl group; Or a substituted group of CD ₃ or C1-C10 alkyl group or C2-C20 heterocyclic group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently deuterium; Fluorine; Methyl group; t-butyl group; CD ₃ ; Adamantyl group; CF ₃ ; Trimethylsilyl group; A phenyl group unsubstituted or substituted with deuterium, fluorine, methyl group, t-butyl group, CD ₃ , CF ₃ , or pyridine group; Naphthyl group; A terphenyl group unsubstituted or substituted with deuterium; A fluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a t-butyl group; a dibenzothiophene group unsubstituted or substituted with a t-butyl group; A carbazole group unsubstituted or substituted with a phenyl group; Or a pyridine group unsubstituted or substituted with a methyl group, CD ₃ , or CF ₃ .

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently deuterium; Fluorine; Methyl group; t-butyl group; CD ₃ ; Adamantyl group; CF ₃ ; Trimethylsilyl group; A phenyl group unsubstituted or substituted with deuterium; Naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group; Dibenzofuran group; Dibenzothiophene group; A carbazole group unsubstituted or substituted with a phenyl group; Or a pyridine group unsubstituted or substituted with a methyl group, CD ₃ , or CF ₃ .

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently deuterium; Fluorine; Methyl group; t-butyl group; CD ₃ ; Adamantyl group; CF ₃ ; Trimethylsilyl group; Phenyl group; Naphthyl group; Fluorenyl group; Dibenzofuran group; Dibenzothiophene group; Carbazole; Or a pyridine group.

In one embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formula 2 below.

[Formula 2]

In Chemical Formula 2,

R1, R2 and X to Z are the same as defined in Formula 1,

Q1 to Q3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

q1 to q3 are each an integer of 0 to 3, and when q1 to q3 are each 2 or more, the substituents in parentheses are the same or different from each other.

In one embodiment of the present specification, definitions of Q1 to Q3 are the same as those of the Q.

In one embodiment of the present specification, Q1 to Q3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C1-C10 alkoxy group; A substituted or unsubstituted C6-C40 arylamine group; A substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted C2-C20 heterocyclic group.

In one embodiment of the present specification, Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted C6-C30 aryl group.

In one embodiment of the present specification, Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A C1-C10 alkyl group unsubstituted or substituted with deuterium; Or a C6-C30 aryl group unsubstituted or substituted with deuterium or halogen groups.

In one embodiment of the present specification, Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C1-C5 alkyl group; Or a C6-C20 aryl group unsubstituted or substituted with a halogen group.

In one embodiment of the present specification, Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Or a phenyl group unsubstituted or substituted with a fluoro group.

In one embodiment of the present specification, Q3 is hydrogen; heavy hydrogen; Halogen group; C1-C10 alkyl group; C1-C10alkoxy group; C1-C30 trialkylsilyl group; C6-C60 arylamine group; C6-C30Aryl group; And a C2-C30 heterocyclic group, or one or more substituents selected from the group, or two or more groups selected from the group.

In one embodiment of the present specification, Q3 is hydrogen; heavy hydrogen; Halogen group; C1-C10 alkyl group; C1-C30 trialkylsilyl group; C6-C60 arylamine group; C6-C30Aryl group; And a C2-C30 heterocyclic group, or one or more substituents selected from the group, or two or more groups selected from the group.

In one embodiment of the present specification, Q3 is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Q3 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Q3 is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C1-C10 alkoxy group; A substituted or unsubstituted C6-C60 arylamine group; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heterocyclic group.

In one embodiment of the present specification, Q3 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C6-C60 arylamine group; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heterocyclic group.

In one embodiment of the present specification, Q3 is hydrogen; heavy hydrogen; Halogen group; A C1-C10 alkyl group unsubstituted or substituted with deuterium; A C1-C10 alkoxy group unsubstituted or substituted with a halogen group; C6-C60 arylamine group unsubstituted or substituted with deuterium or C1-C30 trialkylsilyl group; C6-C30 aryl group unsubstituted or substituted with deuterium, halogen group or C1-10 alkyl group; Or a C2-C30 heterocyclic group unsubstituted or substituted with deuterium or a C1-10 alkyl group.

In one embodiment of the present specification, Q3 is hydrogen; heavy hydrogen; Halogen group; A C1-C10 alkyl group unsubstituted or substituted with deuterium; C6-C40 arylamine group unsubstituted or substituted with deuterium or C1-C30 trialkylsilyl group; C6-C20 aryl group unsubstituted or substituted with deuterium, halogen group or C1-10 alkyl group; Or a C2-C20 heterocyclic group unsubstituted or substituted with deuterium or a C1-10 alkyl group.

In one embodiment of the present specification, Q3 is hydrogen; heavy hydrogen; Halogen group; A C1-C5 alkyl group unsubstituted or substituted with deuterium; C6-C40 arylamine group unsubstituted or substituted with deuterium or C1-C15 trialkylsilyl group; C6-C20 aryl group unsubstituted or substituted with deuterium, halogen group or C1-C5 alkyl group; Or a C2-C20 heterocyclic group unsubstituted or substituted with deuterium or a C1-C5 alkyl group.

In one embodiment of the present specification, Q3 is hydrogen; heavy hydrogen; Fluoro groups; Methyl group; t-butyl group; Trifluoromethoxy group; A diphenylamine group unsubstituted or substituted with deuterium or trimethylsilyl group; A phenyl group unsubstituted or substituted with deuterium, a fluoro group, or a t-butyl group; Or a carbazole group unsubstituted or substituted with a t-butyl group.

In one embodiment of the present specification, Q3 is hydrogen; heavy hydrogen; Methyl group; t-butyl group; A diphenylamine group unsubstituted or substituted with deuterium or trimethylsilyl group; A phenyl group unsubstituted or substituted with deuterium, a fluoro group, or a t-butyl group; Or a carbazole group unsubstituted or substituted with a t-butyl group.

In one embodiment of the present specification, Q3 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C6-C40 arylamine group; A substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted C2-C20 heterocyclic group.

In one embodiment of the present specification, q1 is an integer from 0 to 3.

In one embodiment of the present specification, q2 is an integer from 0 to 3.

In one embodiment of the present specification, q3 is an integer from 0 to 3.

In one embodiment of the present specification, q1 is 1.

In one embodiment of the present specification, q2 is 1.

In one embodiment of the present specification, q3 is 1.

In one embodiment of the present specification, when q1 is 2 or more, a plurality of Q1s are the same or different from each other. In another exemplary embodiment, when q2 is 2 or more, a plurality of Q2s are the same or different from each other. In another exemplary embodiment, when q3 is 2 or more, a plurality of Q3s are the same or different from each other.

In one embodiment of the present specification, Chemical Formula 3 is represented by any one of the following Chemical Formulas 301 to 303.

[Chemical Formula 301]

[Chemical Formula 302]

[Formula 303]

In the above formulas 301 to 303,

The definitions of R1, R2, L11, L12, Ar1, Ar2, n11 and n12 are as defined in Formula 1,

Y1 is O; Or S,

Z1 is O; Or S,

Q1 to Q3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Y1 is O.

In one embodiment of the present specification, Y1 is S.

In one embodiment of the present specification, Z1 is O.

In one embodiment of the present specification, Z1 is S.

In one embodiment of the present specification, Q1 to Q3 in Chemical Formulas 301 to 303 are the same as the definitions of Q1 to Q3 in Chemical Formula 2.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently a substituted or unsubstituted benzene ring,

X is B,

L11 and L12 are the same as or different from each other, and each independently a direct bond; Or a C6-C20 arylene group unsubstituted or substituted with a C1-C5 alkyl group,

Ar1 and Ar2 are the same or different from each other, and each independently a deuterium and a C1-C5 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of alkyl groups of C1-C5 or two or more groups selected from the group; Or a C2-C20 heterocyclic group.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is any one selected from the following compounds.

The compound according to one embodiment of the present specification may be prepared by a manufacturing method described later. If necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, starting materials, reactants, reaction conditions, etc. can be changed based on techniques known in the art.

For example, the compound represented by Formula 1 may have a core structure as shown in Formula 1 below. Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be changed according to techniques known in the art. Substituents may be combined as shown in Formula 1 below, but are not limited thereto.

[Formula 1]

In Formula 1, A1 to A3, R11, R12, Y and R2 are defined as defined in Formula 1.

Intermediate IM-3 can be obtained by coupling reaction using Pd catalyst of intermediate IM-1 and intermediate IM-2 or ring formation or SNAr reaction using acid, and in this process, only when R2 of formula 1 is phenyl group However, the intermediate IM-3 in which R2 is an aryl group other than a phenyl group can be synthesized using an aryl group other than a phenyl group. From the intermediate IM-3, a compound having Formula 1 can be synthesized by a Li-X exchange reaction followed by a boron addition reaction.

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

This specification is the first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1 do.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes a compound represented by the formula (1).

When a member is referred to herein as being “on” another member, this includes not only the case where one member abuts another member, but also the case where another member exists between the two members.

In the present specification, when a part “includes” a certain component, it means that the component may further include other components, not to exclude other components, unless specifically stated otherwise.

In the present specification, the'layer' is a meaning compatible with the'film' mainly used in the technical field, and refers to a coating covering a desired area. The size of the'layer' is not limited, and each'layer' may have the same or different sizes. In an exemplary embodiment, the size of the'layer' may be the same as that of the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.

In the present specification, the meaning that a specific A material is included in the B layer means i) one or more A materials are included in one B layer, and ii) the B layer is composed of one or more layers, and the A material is a multilayer B. All of the layers included in one or more layers are included.

In the present specification, the meaning that a specific A material is included in the C layer or the D layer includes i) one or more of the C layers of one or more layers, ii) one or more of the D layers of one or more layers, or iii ) It means both included in each of the C layer of one or more layers and the D layer of one or more layers.

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

The organic material layer of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light emitting device is not limited to this, and may include fewer organic layers.

The organic light emitting diode according to the exemplary embodiment of the present specification includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 and a compound represented by Formula H below.

[Formula H]

In the formula H,

L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R21 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted 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,

Ar101 and Ar102 are the same as or different from each other, and 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 as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6-C30 arylene group; Or a substituted or unsubstituted C2-C30 heteroarylene group containing N, O, or S.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; C6-C20arylene group; Or a C2-C20 heteroarylene group containing N, O, or S. The arylene group or heteroarylene group is substituted or unsubstituted with a C1-C10 alkyl group, a C6-C20 aryl group, or a C2-C20 heteroaryl group. In another exemplary embodiment, the'substituted or unsubstituted' refers to a C1-C10 alkyl group, a C6-C20 aryl group, or a C2-C20 heteroaryl group, or no substituent.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted naphthylene group; Or a substituted or unsubstituted thiophenylene group.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; Phenylene group; Naphthylene group; Or a thiophenylene group.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a naphthylene group.

In one embodiment of the present specification, L21 and L22 are a direct bond.

In one embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group; Or a C2-C30 heteroaryl group unsubstituted or substituted with Y1.

In one embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C20 aryl group with Y1; Or a C2-C20 heteroaryl group unsubstituted or substituted with Y1.

In one embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a monocyclic to 4 ring aryl group which is unsubstituted or substituted with Y1; Or a monocyclic to 4 ring heteroaryl group unsubstituted or substituted with Y1.

In one embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; Or dibenzofuran group.

In one embodiment of the present specification, Y1 is deuterium; Halogen group; Nitrile group; C1-C10 alkyl group; A cycloalkyl group having 3 to 20 carbon atoms; A silyl group substituted with an alkyl group of C1-C10; Or it is a C6-C30 aryl group.

In one embodiment of the present specification, Y1 is deuterium; Halogen group; Nitrile group; C1-C5 alkyl group; A cycloalkyl group having 3 to 10 carbon atoms; C1-C5 alkyl group substituted silyl group; Or it is a C6-C20 aryl group.

In one embodiment of the present specification, Y1 is deuterium; Halogen group; Nitrile group; Methyl group; Cyclohexyl group; Trimethylsilyl group; Or a phenyl group.

In one embodiment of the present specification, Y1 is deuterium; Fluorine; Nitrile group; Methyl group; Cyclohexyl group; Or a trimethylsilyl group.

In one embodiment of the present specification, R21 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted 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.

In one embodiment of the present specification, R21 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted 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 C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heteroaryl group.

In one embodiment of the present specification, R21 to R28 are each hydrogen; Or deuterium.

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

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

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

The organic light emitting device according to an exemplary embodiment of the present specification includes a light emitting layer, the light emitting layer includes a compound represented by Formula 1 as a dopant in the light emitting layer, and a compound represented by Formula H as a host of the light emitting layer.

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

In one embodiment of the present specification, the emission layer may further include a host material in addition to the compound represented by Chemical Formula H. At this time, the host material (mixed host compound) further included may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, Pyrimidine derivatives, and the like, but are not limited thereto.

The mixing ratio of the compound represented by Formula H and the mixed host compound is 95:5 to 5:95.

In one embodiment of the present specification, the light emitting layer including the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula H has a blue color.

The organic light emitting diode according to the exemplary embodiment of the present specification includes two or more light emitting layers, and at least one of the two or more light emitting layers includes a compound represented by Formula 1 and a compound represented by Formula H. The light emitting layer including the compound represented by Formula 1 and the compound represented by Formula H has a blue color, and the light emitting layer not containing the compound represented by Formula 1 and the compound represented by Formula H is blue known in the art, Red or green light-emitting compounds.

In one embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer.

In one embodiment of the present specification, the organic material layer includes an electron injection layer or an electron transport layer.

In one embodiment of the present specification, the organic material layer includes an electron blocking layer.

In one embodiment of the present specification, the organic material layer includes a hole blocking layer.

In one embodiment of the present specification, the organic light emitting device is a hole injection layer, a hole transport layer. It further includes at least one layer or two or more layers selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

In one embodiment of the present specification, the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; A light emitting layer provided between the first electrode and the second electrode; And two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode.

In one embodiment of the present specification, two or more organic material layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a layer simultaneously performing hole transport and hole injection, and an electron blocking layer.

In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

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

In FIG. 1, 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 is illustrated. The compound represented by Chemical Formula 1 is included in the light emitting layer. According to an exemplary embodiment of the present specification, the compound represented by the formula (H) may be further included in the light emitting layer.

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 the exemplary embodiment of the present specification, the compound represented by Chemical Formula 1 is included in the light emitting layer. According to an exemplary embodiment of the present specification, the compound represented by the formula (H) may be further included in the light emitting layer. According to another exemplary embodiment, the compound represented by Chemical Formula 1 is included in a hole injection layer or a hole transport layer.

3, the anode 102, the hole injection layer 103, the hole transport layer 104, the electron blocking layer 105, the light emitting layer 106, the hole blocking layer 107, the electron transport layer 108 on the substrate 101 , The structure of the organic light emitting device in which the electron injection layer 109 and the cathode 110 are sequentially stacked is illustrated. According to the exemplary embodiment of the present specification, the compound represented by Chemical Formula 1 is included in the light emitting layer. According to an exemplary embodiment of the present specification, the compound represented by the formula (H) may be further included in the light emitting layer. According to another exemplary embodiment, the compound represented by Chemical Formula 1 is included in a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, or an electron injection layer.

The organic light emitting device of the present specification may be made of materials and methods known in the art, except that the light emitting layer includes the compound, that is, the compound represented by Formula 1 and the compound represented by Formula H.

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

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a positive electrode is deposited by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. It can be produced by forming and forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by the formula (1) or the compound represented by the formula (H) may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light emitting device may be made by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate. However, the manufacturing method is not limited thereto.

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

In another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

The positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer. Metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : combination of metal and oxide such as Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into an organic material layer. Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; A multilayer structure material such as LiF/Al or LiO ₂ /Al, and the like, 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 Chemical Formula 1 or the compound represented by Chemical Formula H. The additional emissive layer can include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, Pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, examples of the aromatic amine derivative include condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and periplanene having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or two or more are selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups. The substituent is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.

The hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injection effect for the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of the exciton generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. Also, a material having excellent thin film formation ability is preferred. In addition, it is preferable that the high-occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, and arylamine-based organic materials; Hexanitrile hexaaza triphenylene series organics; Quinacridone-based organic matter; Perylene-based organic substances; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. As the hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is preferably a material having high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons is preferable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer can be used with any desired negative electrode material, as used according to the prior art. Particularly, a suitable negative electrode material has a low work function and is a conventional material followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.

The electron injection layer is a layer that receives electrons from an electrode. It is preferable that the electron injecting agent has an excellent electron transporting ability and an electron receiving effect from the second electrode, and an excellent electron injection effect for the light emitting layer or the light emitting material. In addition, a material that prevents exciton generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, Metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

The metal complex compound includes 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, and bis(8-hydroxyquinolinato) manganese , Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h ]Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , But is not limited thereto.

The electron blocking layer is a layer capable of improving the life and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer. Known materials can be used without limitation, and can be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and the layer simultaneously performing hole injection and hole transport.

The hole blocking layer is a layer that blocks reaching the cathode of the hole, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but are not limited thereto.

The organic light emitting device according to the present specification may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.

Hereinafter, examples and comparative examples will be described in detail to specifically describe the present specification. However, the examples and comparative examples according to the present specification may be modified in various other forms, and the scope of the present specification is not interpreted to be limited to the examples and comparative examples described below. The examples and comparative examples in the present specification are provided to more fully describe the present specification to those skilled in the art.

합성예Synthetic example

합성예 1.Synthesis Example 1.

Starting materials S-1 (10 g), S-2 (20.6 g, 1.1 eq), Pd (P t Bu ₃ ) ₂ (0.31 g, 0.02 eq), NaO t Bu (8.8 g, 3 eq) and toluene (300 ml) The flask containing) was heated at 110° C. and stirred for 16 hours. The reaction solution was cooled to room temperature, water and toluene were added for separation, and the solvent was distilled off under reduced pressure. Purified by silica gel column chromatography (eluent:toluene/hexane) to obtain compound S-3 (9.7 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H] ⁺ =781.

Here, t Bu means tert-butyl group.

합성예 2.Synthesis Example 2.

To a flask containing intermediate S-3 (8 g) and toluene (70 ml), a solution of n-butyllithium pentane (8.2 ml, 2.5 M in hexane, 2 equivalents) was added at 0° C. under a nitrogen atmosphere. After completion of dropping, the mixture was heated to 50°C and stirred for 2 hours. After cooling to -40°C, boron tribromide (1.5 ml, 1.5 eq.) was added, the temperature was raised to room temperature and stirred for 4 hours. Thereafter, the mixture was cooled to 0° C. again, and Sat.aq.NaHCO ₃ and ethyl acetate were added for separation, and then the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography (developer: hexane/toluene) gave compound A-2 (1.2 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H]+=711.

합성예 3.Synthesis Example 3.

In Synthesis Example 1, 11.8 g of Intermediate S-5 was obtained using S-4 (20.6 g) in the same manner as the method for preparing Compound S-3. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H] ⁺ =997.

합성예 4.Synthesis Example 4.

In Synthesis Example 2, 1.2 g of Compound A-5 was obtained using S-5 (10 g) in the same manner as the method for preparing Compound A-2. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H] ⁺ =927.

합성예 5.Synthesis Example 5.

In Synthesis Example 1, 11.4 g of Intermediate S-7 was obtained by using S-6 (10 g) and S-1 (22.2 g) in the same manner as the method for preparing Compound S-3. As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H] ⁺ =757.

합성예 6.Synthesis Example 6.

Intermediate S-7 (9.5 g), S-8 (3.7 g, 1.05 eq), Pd (P t Bu ₃ ) ₂ (0.13 g, 0.02 eq), NaO t Bu (1.8 g, 1.5 eq) and toluene (40 ml) The flask containing) was heated at 110° C. and stirred for 4 hours. The reaction solution was cooled to room temperature, water and toluene were added for separation, and the solvent was distilled off under reduced pressure. Purification by recrystallization (ethyl acetate/hexane) gave compound S-9 (10.5 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H] ⁺ =1001.

합성예 7.Synthesis Example 7.

In Synthesis Example 1, 12.9 g of Intermediate S-11 was obtained using S-6 (10 g) and S-10 (25.7 g) in the same manner as the method for preparing Compound S-3. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H] ⁺ =853.

합성예 8.Synthesis Example 8.

In Synthesis Example 6, 10.6 g of Intermediate S-13 was obtained using S-11 (11 g) and S-12 (3.3 g) in the same manner as the method for preparing Compound S-9. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H] ⁺ =1058.

합성예 9.Synthesis Example 9.

To a flask containing intermediate S-9 (9.0 g) and toluene (60 ml), a 1.7 M tert-butyllithium pentane solution (21.1 ml, 4 eq.) was added at 0° C. under a nitrogen atmosphere. After completion of dropping, the mixture was heated to 70°C and stirred for 2 hours. After cooling to -40°C, boron tribromide (1.7 ml, 2 eq.) was added, the temperature was raised to room temperature and stirred for 4 hours. Sat.aq. Na ₂ S ₂ O ₃ and sat.aq. After adding NaHCO ₃ and separating, the solvent was distilled off under reduced pressure. Purification by recrystallization (hexane/toluene) gave compound A-4 (1.4 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H] ⁺ =975.

합성예 10.Synthesis Example 10.

In Synthesis Example 9, 0.9 g of Compound A-6 was obtained using S-13 (9.6 g) in the same manner as the method of preparing Compound A-4. As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H] ⁺ =1032.

합성예 11.Synthesis Example 11.

In Synthesis Example 1, 12.5 g of Intermediate S-15 was obtained using S-2 (10 g) and S-14 (20.6 g) in the same manner as the method for preparing Compound S-3. As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H] ⁺ =933.

In Synthesis Example 2, 2.1 g of Compound A-3 was obtained using S-15 (11 g) in the same manner as the method for preparing Compound A-2. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H] ⁺ =863.

합성예 12.Synthesis Example 12.

In Synthesis Example 1, 14.2 g of Intermediate S-17 was obtained by using S-2 (15 g) and S-16 (28 g) in the same manner as the method for preparing Compound S-3. As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H] ⁺ =724.

In Synthesis Example 2, 1.3 g of Compound B-2 was obtained using S-17 (13 g) in the same manner as the method of preparing Compound A-2. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H] ⁺ =654.

합성예 13.Synthesis Example 13.

In Synthesis Example 1, 10.6 g of Intermediate S-19 was obtained using S-2 (10 g) and S-18 (20.9 g) in the same manner as the method for preparing Compound S-3. As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H] ⁺ =792.

In Synthesis Example 2, 1.2 g of Compound B-3 was obtained using S-19 (9.6 g) in the same manner as the method of preparing Compound A-2. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H] ⁺ =722.

합성예 14.Synthesis Example 14.

The flask containing intermediate S-20 (47.1 g, 1.15 eq), S-21 (20 g), K ₂ CO ₃ (28.3 g, 2.5 eq) and N,N-dimethylacetamide (DMAC) (400 mL) was heated at 160°C And stirred for 12 hours. After cooling to room temperature, ethyl acetate (400 mL) and water (250 mL) were added for separation, and then the organic layer was aq. It was washed twice with NaCl. The solvent of the organic layer was distilled off under reduced pressure, and purified by silica gel column chromatography (developer: hexane/toluene) to obtain intermediate S-22 (33.8 g).

The flask containing intermediate S-22 (32 g), Pd (P t Bu ₃ ) ₂ (0.68 g, 0.03 equiv), NaO t Bu (8.5 g, 2 equiv) and toluene (450 ml) was heated at 110° C., 12 Stir for hours. The reaction solution was cooled to room temperature, water and toluene were added for separation, and the solvent was distilled off under reduced pressure. Purification by recrystallization (ethyl acetate/hexane/acetonitrile) gave compound S-23 (18.2 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H] ⁺ =642.

합성예 15.Synthesis Example 15.

Under nitrogen atmosphere, add compound S-23 (8g), S-24 (2.1g, 1.3 eq) potassium carbonate (62.2g, 1.5 eq), dioxane 45mL and water 15mL Pd(P t Bu ₃ ) ₂ (0.1 g, 0.0015 eq), was added, heated at 120° C. and stirred for 6 hours. After the reaction was completed, the reaction solution was cooled to room temperature, separated by adding water and ethyl acetate, and filtered through MgSO ₄ (anhydrous) treatment. The filtered solution was distilled off under reduced pressure and purified by recrystallization (ethylacetate/hexane) to obtain 7.2 g of intermediate S-25. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+] = 689.

합성예 16.Synthesis Example 16.

In Synthesis Example 9, 1.1 g of Compound C-1 was obtained using S-25 (6.5 g) in the same manner as in Compound A-4. As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H] ⁺ = 663.

합성예 17.Synthesis Example 17.

In Synthesis Example 15, 8.1 g of Compound S-27 was obtained using S-26 (2.9 g) in the same manner as the method of preparing Compound S-25. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H] ⁺ =740.

In Synthesis Example 9, Compound C-2 (1.0 g) was obtained using S-27 (7.5 g) in the same manner as in Compound A-4. As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H] ⁺ =714.

합성예 18.Synthesis Example 18.

In Synthesis Example 14, 29 g of Compound S-29 was obtained using S-21 (15 g), and S-28 (45 g) in the same manner as in Compound S-23, and S-30 17.9 using S-29 obtained. g was obtained. As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H] ⁺ =778.

합성예 19.Synthesis Example 19.

In Synthesis Example 15, 7.8 g of Compound S-32 was obtained using S-30 (8.5 g) and S-31 (2.2 g) in the same manner as the method for preparing Compound S-25. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H] ⁺ =856.

In Synthesis Example 9, 0.9 g of Compound D-1 was obtained using S-32 (7 g) in the same manner as in Compound A-4. As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H] ⁺ =830.

실험예 1.Experimental Example 1.

HOMO in the absorption state of the molecule using the TD-DFT (B3LYP) method/6-31G* basis method. The energy levels of LUMO and singlet (S ₁ ) and the oscillator strength of singlet (radiation transition probability, f) were calculated. The calculation results are shown in Table 1 below. In Table 1, the substituents of C, Y, and Z are substituents corresponding to Formula 1 of the present invention. C is a substituent corresponding to the carbon site of the bridge alkyl located between the A1 ring and the A2 ring of Formula 1.

	비교예 1Comparative Example 1	비교예 2Comparative Example 2	비교예 3Comparative Example 3	비교예 4Comparative Example 4
	화합물 X-1Compound X-1	화합물 X-2Compound X-2	화합물 X-3Compound X-3	화합물 X-4Compound X-4
치환기Substituent	Y, Z=NPhY, Z=NPh
치환기Substituent	C=NPhC=NPh	C=OC=O	C=SC=S	C=H,HC=H,H
HOMO (eV)HOMO (eV)	4.714.71	4.914.91	4.894.89	4.744.74
LUMO (eV)LUMO (eV)	0.560.56	0.820.82	0.990.99	1.071.07
S₁ (eV)S ₁ (eV)	3.57 3.57	3.52 3.52	3.32 3.32	3.14 3.14
ff	0.114 0.114	0.156 0.156	0.14 0.14	0.205 0.205
	실시예 1Example 1	실시예 2Example 2	비교예 5Comparative Example 5	비교예 6Comparative Example 6
	화합물 A-1Compound A-1	화합물 B-1Compound B-1	화합물 X-5Compound X-5	화합물 X-6Compound X-6
치환기Substituent	Y, Z=NPhY, Z=NPh		C,Y,Z=OC,Y,Z=O	C,Y,Z=C(CH₃)₂ C,Y,Z=C(CH ₃ ) ₂
치환기Substituent	C=C(Ph)₂ C=C(Ph) ₂	C=C(Ph)(CH₃)C=C(Ph)(CH ₃ )	C,Y,Z=OC,Y,Z=O	C,Y,Z=C(CH₃)₂ C,Y,Z=C(CH ₃ ) ₂
HOMO (eV)HOMO (eV)	4.784.78	4.744.74	5.885.88	6.206.20
LUMO (eV)LUMO (eV)	1.081.08	0.970.97	1.411.41	1.561.56
S₁ (eV)S ₁ (eV)	3.16 3.16	3.24 3.24	3.903.90	4.03 4.03
ff	0.174 0.174	0.191 0.191	0.070.07	0.071 0.071

The emission wavelength of the compound is a value shifted by the Stokes shift from the absorption wavelength, and the degree of the emission wavelength can be predicted as the absorption wavelength.

The radiative transition probability (f) is a measure of fluorescence quantum efficiency and is calculated by the following equation. The greater the value of the radiation transition probability (f), the greater the luminous efficiency.

Looking at the results of Comparative Examples 1 to 4, as in Comparative Example 4, when the bridge alkyl of Formula 1 is not included (when C is H and H), the energy value of singlet(S ₁ ) is 3.14 eV. As in Comparative Examples 1 to 3, when C is replaced with NPh, O, and S, respectively, it can be seen that the S ₁ energy value becomes very large and the f value also decreases to 0.15 or less. A large S ₁ energy value means that the maximum emission wavelength is a short wavelength, and a smaller f value means that the luminous efficiency is reduced.

Also, in Comparative Examples 5 to 6, when C, Y, and Z are all carbon or oxygen, it can be seen that the S ₁ energy value becomes very large and the f value also becomes very small. On the other hand, it is confirmed that compounds A-1 and B-1 represented by Chemical Formula 1 of the present invention have S ₁ energy values and f values similar to those of Compound X-4 (which does not include bridged alkyl). can do. Referring to the device example to be described later, the compound represented by Formula 1 of the present invention (including the bridge alkyl of C) may have a longer life effect than the compound X-8 that does not contain the bridge alkyl.

Looking at the maximum emission wavelength of the compounds X-1,5,6, it is very short wavelength, and is not suitable for application to a blue organic light emitting device, so low efficiency is expected.

화합물compound	X-1X-1	X-4X-4	X-5X-5	X-6X-6
치환기Substituent	Y, Z=NPhY, Z=NPh		C,Y,Z=OC,Y,Z=O	C,Y,Z=C(CH₃)₂ C,Y,Z=C(CH ₃ ) ₂
치환기Substituent	C=NPhC=NPh	C=H,HC=H,H	C,Y,Z=OC,Y,Z=O	C,Y,Z=C(CH₃)₂ C,Y,Z=C(CH ₃ ) ₂
PL-max(nm)PL-max(nm)	403^a(0.02mM, DCM)403 ^a (0.02mM, DCM)	462^b(0.02mM, DCM)462 ^b (0.02mM, DCM)	386^c(0.01mM, THF)386 ^c (0.01 mM, THF)	407^d(0.01mM, THF)407 ^d (0.01 mM, THF)

실험예 2. 소자예Experimental Example 2. Device Example

실시예 3.Example 3.

A glass substrate coated with a thin film of indium tin oxide (ITO) at a thickness of 1300 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as a detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.

On the prepared ITO transparent electrode, the following compound HAT was thermally vacuum-deposited to a thickness of 50 Pa to form a hole injection layer. Then, the following compound HT-A 1000Å was vacuum-deposited as a first hole transport layer, and subsequently the following compound HT-B 100Å was deposited as a second hole transport layer. The host BH-A and the dopant Compound A-2 were vacuum-deposited at a weight ratio of 97: 3 to form a 200-mm thick light emitting layer.

Subsequently, 50 µm of the following compound ET-A was vacuum-deposited as the first electron transport layer, and 300 µm of the following compound ET-B and the following compound Liq in a 1:1 ratio as a second electron transport layer simultaneously performing electron injection and electron transport. Deposition was performed, and magnesium and silver (mass ratio 10:1) were sequentially deposited on the same surface at a thickness of 500 Pa to form a cathode, thereby manufacturing an organic light emitting device.

In the above process, the deposition rate of the organic matter was maintained at 0.4 to 1.0 Å/sec, and the deposition rate of silver and magnesium was maintained at 2 Å/sec. The vacuum degree during deposition was 5 × 10 ^-8 to 1 × 10 ^-7 torr. By maintaining the, an organic light emitting device was produced.

실시예 4 내지 13Examples 4 to 13

An organic light-emitting device was manufactured in the same manner as in Example 3, except that the host and dopant compounds shown in Table 3 below were used as the light-emitting layer material in Example 3.

비교예 7 내지 9Comparative Examples 7 to 9

The organic light emitting devices manufactured by Examples 3 to 13 and Comparative Examples 7 to 9 were measured for luminous efficiency (cd/A) at a current density of 10 mA/cm ² , and the results are shown in Table 2 below. The lifetime was measured at 20 mA/cm ² , which is 97% of the initial luminance (T97).

	호스트(발광층)Host (light emitting layer)	도펀트(발광층)Dopant (light emitting layer)	10mA/cm² 10mA/cm ²	20mA/cm² 20mA/cm ²
	호스트(발광층)Host (light emitting layer)	도펀트(발광층)Dopant (light emitting layer)	발광효율(Cd/A)Luminous efficiency (Cd/A)	수명, T97(시간)Lifetime, T97 (hours)
실시예 3Example 3	BH-ABH-A	A-2A-2	5.6 5.6	94 94
실시예 4Example 4	BH-ABH-A	A-4A-4	5.9 5.9	95 95
실시예 5Example 5	BH-ABH-A	A-5A-5	5.4 5.4	84 84
실시예 6Example 6	BH-ABH-A	A-6A-6	6.2 6.2	91 91
실시예 7Example 7	BH-ABH-A	B-2B-2	5.3 5.3	90 90
실시예 8Example 8	BH-ABH-A	C-1C-1	5.4 5.4	86 86
실시예 9Example 9	BH-BBH-B	A-2A-2	5.5 5.5	91 91
실시예 10Example 10	BH-BBH-B	A-4A-4	5.7 5.7	93 93
실시예 11Example 11	BH-BBH-B	A-6A-6	6.0 6.0	89 89
실시예 12Example 12	BH-BBH-B	B-3B-3	5.4 5.4	87 87
실시예 13Example 13	BH-BBH-B	D-1D-1	5.3 5.3	85 85
비교예 7Comparative Example 7	BH-ABH-A	X-7X-7	5.0 5.0	82 82
비교예 8Comparative Example 8	BH-BBH-B	X-7X-7	4.8 4.8	73 73
비교예 9Comparative Example 9	BH-BBH-B	X-8X-8	5.2 5.2	58 58

Looking at Table 3, it can be seen that the device including the compound represented by Chemical Formula 1 of the present invention has excellent luminous efficiency and long life. In particular, the compound represented by the formula (1) is a compound having a longer life property than the compound X-8, which is higher in efficiency than the compound X-7 in which R1 and R2 in the formula 1 of the present invention are both alkyl groups.

실험예 3: 도펀트 도핑 농도에 따른 발광 효율 변화 Experimental Example 3: Emission efficiency change according to dopant doping concentration

실시예 14, 비교예 10Example 14, Comparative Example 10

In Example 3, a dopant compound shown in Table 4 was used as a light emitting layer material, and the organic light emitting device was manufactured in the same manner as in Example 3, except that the host and the dopant were vacuum deposited in a weight ratio of 99:1 to 95:5. Was prepared.

The organic light-emitting device manufactured by Example 14 and Comparative Example 10 was measured for the light emission efficiency (EQE) at a current density of 10 mA/cm ² . The luminous efficiency according to the doping concentration of Compound A-2 (Example 14) is illustrated in FIG. 4, and the luminous efficiency according to the doping concentration of Compound X-7 (Comparative Example 10) is illustrated in FIG. 5.

	도펀트(발광층)Dopant (light emitting layer)	EQE, 10mA/cm₂ EQE, 10mA/cm ₂
		도핑농도Doping concentration
		1%One%	2%2%	3%3%	4%4%	5%5%
실시예 14Example 14	화합물 A-2Compound A-2	5.035.03	5.615.61	5.765.76	5.795.79	5.815.81
비교예 10Comparative Example 10	화합물 X-7Compound X-7	5.145.14	5.275.27	5.215.21	5.165.16	5.105.10

Compound A-2 satisfying Chemical Formula 1 can be confirmed that the concentration quenching effect decreases as the doping concentration increases due to the effect of the bulkiness of the molecule than that of Compound X-7.

Claims

Compound represented by the formula (1):

[Formula 1]

In Chemical Formula 1,

A1 to A3 are the same as or different from each other, and each independently an substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,

X is B or N,

Y is N(R11), Z is O; S; Or N(R12),

Y is O; S; Or N(R11), Z is N(R12),

R1 is a substituted or unsubstituted aryl group,

R2 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

R11 is -(L11)n11-Ar1,

R12 is -(L12)n12-Ar2,

L11 and L12 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar1 and Ar2 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n11 and n12 are the same as or different from each other, and each independently 1 or 2,

When n11 is 2, L11 is the same as or different from each other,

When n12 is 2, L12 is the same as or different from each other.
The method according to claim 1, wherein Formula 1 is a compound represented by Formula 2:

[Formula 2]

In Chemical Formula 2,

R1, R2 and X to Z are the same as defined in Formula 1,

Q1 to Q3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

q1 to q3 are each an integer of 0 to 3, and when q1 to q3 are each 2 or more, the substituents in parentheses are the same or different from each other.
The method according to claim 1, wherein Formula 1 is a compound represented by any one of the following formulas 301 to 303:

[Chemical Formula 301]

[Chemical Formula 302]

[Formula 303]

In the above formulas 301 to 303,

The definitions of R1, R2, L11, L12, Ar1, Ar2, n11 and n12 are as defined in Formula 1,

Y1 is O; Or S,

Z1 is O; Or S,

Q1 to Q3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

q1 to q3 are each an integer of 0 to 3, and when q1 to q3 are each 2 or more, the substituents in parentheses are the same or different from each other.
The method according to claim 1,

R1 and R2 are the same as or different from each other, and each independently is a C6-C20 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium or C1-C5 alkyl groups or two or more groups selected from the group. Compound.
The method according to claim 1,

A1 to A3 are the same as or different from each other, and each independently a substituted or unsubstituted benzene ring,

X is B,

L11 and L12 are the same as or different from each other, and each independently a direct bond; Or a C6-C20 arylene group unsubstituted or substituted with a C1-C5 alkyl group,

Ar1 and Ar2 are the same or different from each other, and each independently a deuterium and a C1-C5 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of alkyl groups of C1-C5 or two or more groups selected from the group; Or a compound that is a heterocyclic group of C2-C20.
The compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:

.
A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound according to any one of claims 1 to 6 Light emitting element.
The organic light emitting device of claim 7, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.
The organic light emitting device of claim 7, wherein the organic material layer includes a light emitting layer, the light emitting layer includes a dopant material, and the dopant material includes the compound.
The organic light emitting device of claim 7, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer contains the compound.
The organic light emitting device of claim 7, wherein the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or electron transport layer contains the compound.
The method according to claim 7, The organic layer is 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 selected from the group consisting of more than one layer or more organic Light emitting element.