WO2020149663A1 - Organic light-emitting device - Google Patents

Abstract

The present specification provides an organic light-emitting device comprising: 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 layers of the organic material layers include a compound represented by chemical formula 1 and a compound represented by chemical formula 2.

Description

Organic light emitting device

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0006800 filed with the Korean Intellectual Property Office on January 18, 2019, the entire contents of which are incorporated herein.

The present application relates to an organic light emitting device comprising a compound of Formula 1 and a compound of Formula 2.

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.

It is to provide the organic light emitting device of the present application.

This application is the 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,

At least one layer of the organic material layer provides an organic light emitting device comprising the compound of Formula 1 and the compound of Formula 2.

[Formula 1]

In Chemical Formula 1,

A, B and C are each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted heterocycle,

X3 and X4 are each independently O; S; Or NR,

Y1 is boron or phosphine oxide,

R is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

The adjacent groups among R, A, B and C may combine with each other to form a ring,

[Formula 2]

In Chemical Formula 2,

X1 and X2 are each independently O or S,

R1 to R3 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a and b are each independently an integer from 0 to 7,

c is an integer from 0 to 8,

When a to c are each independently an integer of 2 or more, the substituents in parentheses are the same or different from each other.

The organic light emitting device using the compound according to an exemplary embodiment of the present application may have a low driving voltage, high luminous efficiency, and/or long life.

1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.

2, the substrate (1), the anode (2), the hole injection layer (5), the hole transport layer (6), the light emitting layer (3), the electron transport layer (7), the electron injection layer (8) and the cathode (4) sequentially It shows an example of an organic light-emitting device stacked.

1: Substrate

2: anode

3: light emitting layer

4: Cathode

5: hole injection layer

6: hole transport layer

7: electron transport layer

8: Electronic injection layer

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

The present specification provides an organic light emitting device including the compound of Formula 1 and the compound of Formula 2.

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

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; Nitro group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And substituted or unsubstituted heterocyclic groups, substituted with 1 or 2 or more substituents selected from the group, or substituted with 2 or more substituents among the exemplified substituents, or having no substituents. For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are 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 carbon number is not particularly limited, but is preferably 1 to 50. Specific examples are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 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. Does not.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It may be, but is not limited to this.

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, steelbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine groups; N-alkylarylamine group; Arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine groups; Dimethylamine group; Ethylamine group; Diethylamine group; Phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methyl anthracenylamine group; Diphenylamine group; N-phenyl naphthylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenyl naphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenyl terphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, and the like, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula of —SiRaRbRc, wherein Ra, Rb and Rc are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically a trimethylsilyl group; Triethylsilyl group; t-butyldimethylsilyl group; Vinyl dimethyl silyl group; Propyl dimethyl silyl group; Triphenylsilyl group; Diphenylsilyl group; Phenylsilyl group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, 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 has 10 to 24 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, 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,

,

,

And

And the like, but is not limited thereto.

In the present specification, the heterocyclic group includes one or more non-carbon atoms, heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, Isooxazolyl groups, oxadiazolyl groups, thiadiazolyl groups, benzothiazolyl groups, phenothiazinyl groups and dibenzofuranyl groups, and the like, but are not limited thereto.

In the present specification, the description of the aryl group described above may be applied, except that the aromatic hydrocarbon ring is a divalent group.

In the present specification, a description of the aforementioned heterocyclic group may be applied, except that the heterocycle is a divalent group.

In the present specification, the meaning of forming a ring by bonding with adjacent groups to form a ring is a substituted or unsubstituted hydrocarbon ring by bonding with adjacent groups; And it forms a substituted or unsubstituted heterocycle, the hydrocarbon ring and the heterocycle, respectively, may be an aliphatic, aromatic or condensed form thereof, and is not limited thereto.

In the present specification, the aliphatic hydrocarbon ring means a ring composed of only carbon and hydrogen atoms as a ring that is not aromatic.

In the present specification, examples of the aromatic hydrocarbon ring include a phenyl group, a naphthyl group, anthracenyl group, and the like, but are not limited thereto.

In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms.

In the present specification, an aromatic heterocycle means an aromatic ring containing one or more of heteroatoms.

In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocyclic ring and aromatic heterocyclic ring may be monocyclic or polycyclic, respectively.

In the present specification, when adjacent groups are combined with each other to form a ring, adjacent groups may be combined as follows to form a ring.

In the above structure,

A1 to A7 are each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a2 to a7 are each an integer from 0 to 4,

When a2 to a7 are each independently 2 or more, the substituents in parentheses are the same or different from each other,

* Indicates the position to be substituted.

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 at 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.

According to an exemplary embodiment of the present application, A, B and C are each independently, a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In addition, according to an exemplary embodiment of the present application, A, B, and C are each independently, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocycle having 3 to 60 carbon atoms.

In addition, according to an exemplary embodiment of the present application, A, B, and C are each independently, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocycle having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present application, the A, B and C are each independently, substituted or unsubstituted benzene; Substituted or unsubstituted naphthalene; Or substituted or unsubstituted dibenzofuran.

According to an exemplary embodiment of the present application, the A, B and C are each independently, substituted or unsubstituted benzene; Substituted or unsubstituted naphthalene; Or dibenzofuran.

According to an exemplary embodiment of the present application, A is benzene substituted or unsubstituted with one or more substituents selected from the group consisting of amine groups, carbazole groups and alkyl groups; naphthalene; Or dibenzofuran.

According to an exemplary embodiment of the present application, the A is benzene substituted or unsubstituted with one or more substituents selected from the group consisting of diphenylamine, ditolylamine, carbazole group, methyl group and tert-butyl group; naphthalene; Or dibenzofuran.

According to an exemplary embodiment of the present application, B is benzene substituted or unsubstituted with an alkyl group; Or naphthalene unsubstituted or substituted with an alkyl group.

According to an exemplary embodiment of the present application, the B is a benzene substituted or unsubstituted with a methyl group or tert-butyl group; Or naphthalene unsubstituted or substituted with tert-butyl group.

According to an exemplary embodiment of the present application, C is benzene which is unsubstituted or substituted with an alkyl group.

According to an exemplary embodiment of the present application, C is a benzene unsubstituted or substituted with a methyl group or a tert-butyl group.

According to an exemplary embodiment of the present application, Y1 is boron or phosphine oxide.

According to an exemplary embodiment of the present application, Y1 is boron.

According to an exemplary embodiment of the present application, X3 and X4 are each O; S; Or NR.

According to an exemplary embodiment of the present application, X3 and X4 is O.

According to an exemplary embodiment of the present application, X3 and X4 is S.

According to an exemplary embodiment of the present application, X3 and X4 are each NR.

According to an exemplary embodiment of the present application, R is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In addition, according to an exemplary embodiment of the present application, R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In addition, according to an exemplary embodiment of the present application, R is a substituted or unsubstituted aryl group.

In addition, according to an exemplary embodiment of the present application, R is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

In addition, according to an exemplary embodiment of the present application, R is a phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; Or a naphthyl group.

In addition, according to an exemplary embodiment of the present application, R is a phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group; Or a naphthyl group.

According to an exemplary embodiment of the present application, adjacent groups among R, A, B, and C may combine with each other to form a ring.

In addition, according to an exemplary embodiment of the present application, adjacent groups among R, A, B, and C may combine with each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted hetero ring, and may be aliphatic, aromatic, or their It may be in a condensed form.

In addition, according to an exemplary embodiment of the present application, adjacent groups among R, A, B, and C combine with each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms. And may be aliphatic, aromatic, or a condensed form thereof.

In addition, according to an exemplary embodiment of the present application, adjacent groups among R, A, B, and C combine with each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms. And may be aliphatic, aromatic, or a condensed form thereof.

According to an exemplary embodiment of the present application, the formula 1 may be represented by the following formula 1-1.

[Formula 1-1]

In Formula 1-1, the definitions of A, B, C and Y1 are the same as those in Formula 1,

R'and R" are each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryl group Or a substituted or unsubstituted heterocyclic group,

R', R", A, B and C adjacent groups may combine with each other to form a ring.

According to an exemplary embodiment of the present application, R'and R" are each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

Further, according to an exemplary embodiment of the present application, R'and R" are each independently a substituted or unsubstituted aryl group.

In addition, according to an exemplary embodiment of the present application, R'and R" are each independently a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.

Also, according to an exemplary embodiment of the present application, R'and R" are each independently a phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; or a naphthyl group.

Further, according to an exemplary embodiment of the present application, R'and R" are each independently a methyl group or a tert-butyl group-substituted or unsubstituted phenyl group; or a naphthyl group.

According to an exemplary embodiment of the present application, adjacent groups among R', R", A, B, and C may combine with each other to form a ring.

In addition, according to an exemplary embodiment of the present application, adjacent groups among R', R", A, B, and C may combine with each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted hetero ring, and an aliphatic, Aromatic or condensed form thereof.

In addition, according to an exemplary embodiment of the present application, adjacent groups among R', R", A, B, and C are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted carbon number having 2 to 60 carbon atoms. Heterocycles may be formed, and may be aliphatic, aromatic, or condensed forms thereof.

In addition, according to an exemplary embodiment of the present application, adjacent groups among R', R", A, B, and C are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted carbon atom having 2 to 30 carbon atoms. Heterocycles may be formed, and may be aliphatic, aromatic, or condensed forms thereof.

According to an exemplary embodiment of the present application, the formula 1 may be represented by the following formula 1-2.

[Formula 1-2]

In Chemical Formula 1-2,

The definitions of A, B and C are the same as those in formula (1),

R'and R" are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

The adjacent groups among R', R", B and C may combine with each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted hetero ring, and may be aliphatic, aromatic or a condensed form thereof.

According to an exemplary embodiment of the present application, adjacent groups among R', R", B and C are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms. And may be aliphatic, aromatic, or a condensed form thereof.

In addition, according to an exemplary embodiment of the present application, adjacent groups among R', R", B and C are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms. And may be aliphatic, aromatic, or a condensed form thereof.

In addition, according to one embodiment of the present application, adjacent groups of R'and B may combine with each other to form carbazole or spiro [acridine-9,9'-fluorene].

Also, according to an exemplary embodiment of the present application, adjacent groups of R" and C may combine with each other to form carbazole or spiro [acridine-9,9'-fluorene].

According to an exemplary embodiment of the present application, the formula 1 is selected from the following structural formula.

According to an exemplary embodiment of the present application, X1 and X2 are each independently O or S.

According to an exemplary embodiment of the present application, X1 and X2 is O.

According to an exemplary embodiment of the present application, X1 and X2 is S.

According to an exemplary embodiment of the present application, R1 to R3 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present application, R1 to R3 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present application, R1 to R3 are each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present application, R1 to R3 are each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present application, R1 to R3 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; Or a naphthyl group.

According to an exemplary embodiment of the present application, R1 to R3 are each independently hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with deuterium; Or a naphthyl group.

According to an exemplary embodiment of the present application, R1 to R3 are each independently hydrogen; heavy hydrogen; Phenyl group; Or a naphthyl group.

According to an exemplary embodiment of the present application, R1 to R3 are hydrogen, a, b and c are 7, 7, and 8, respectively.

According to an exemplary embodiment of the present application, R1 and R2 are hydrogen, R3 is a phenyl group or a naphthyl group, and a, b and c are 7, 7 and 1, respectively.

According to an exemplary embodiment of the present application, R1 is a phenyl group, R2 and R3 are hydrogen, and a, b and c are 1, 7 and 8, respectively.

According to one embodiment of the present application, R1 and R2 are phenyl groups, R3 is hydrogen, and a, b and c are 1, 1 and 8, respectively.

According to an exemplary embodiment of the present application, R1 to R3 are deuterium.

According to an exemplary embodiment of the present application, R1 and R2 are hydrogen, R3 is deuterium.

According to one embodiment of the present application, R1 and R3 are deuterium, and R2 is hydrogen.

According to one embodiment of the present application, R1 and R2 are deuterium, and R3 is a deuterium or naphthyl group.

According to one embodiment of the present application, R1 and R3 are deuterium, and R2 is a phenyl group substituted with deuterium.

According to an exemplary embodiment of the present application, when R1 is deuterium, a may be an integer from 1 to 7, an integer from 3 to 7, an integer from 5 to 7, and an integer from 6 to 7.

According to an exemplary embodiment of the present application, when R2 is deuterium, b may be an integer from 1 to 7, an integer from 3 to 7, an integer from 5 to 7, and an integer from 6 to 7.

According to an exemplary embodiment of the present application, when R3 is deuterium, c may be an integer of 1 to 8, an integer of 3 to 8, an integer of 5 to 8, an integer of 6 to 8, an integer of 7 to 8.

According to an exemplary embodiment of the present application, at least one of R1 to R3 is deuterium; Or an aryl group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present application, at least one of R1 to R3 is deuterium; A phenyl group unsubstituted or substituted with deuterium; Or a naphthyl group.

According to an exemplary embodiment of the present application, the formula 2 is selected from the following structural formula.

When a member is referred to as being "on" another member in the present application, this includes not only the case where one member is in contact with another member, but also another member between the two members.

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

The organic material layer of the organic light emitting device of the present application 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, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer as an organic material layer. However, the structure of the organic light emitting device is not limited to this, and may include fewer organic layers.

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

In one embodiment of the present application, the organic light emitting device includes 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, and at least one layer of the organic material layer includes the compound of Formula 1 and the compound of Formula 2.

In an exemplary embodiment of the present application, at least one organic layer 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 an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound of Formula 1 and a compound of Formula 2.

The emission layer may include a compound of Formula 1 as a dopant material, and a compound of Formula 2 as a host material.

In one embodiment of the present application, the weight ratio of the compound of Formula 1 and the compound of Formula 2 is 1:99 to 50:50, preferably 1:99 to 10:90, more preferably 3:97 to 7 It can be :93.

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

For example, the structure of the organic light emitting device according to the exemplary embodiment of the present application is illustrated in FIGS. 1 and 2.

1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. In this structure, the compound of Formula 1 and the compound of Formula 2 may be included in the light emitting layer 3.

2, the substrate (1), anode (2), hole injection layer (5), hole transport layer (6), light emitting layer (3), electron transport layer (7), electron injection layer (8) and cathode (4) sequentially The structure of the stacked organic light emitting device is illustrated. In this structure, the compound of Formula 1 and the compound of Formula 2 may be included in the light emitting layer 3.

In one embodiment of the present application, the thickness of the organic material layer containing the compound of Formula 1 and the compound of Formula 2 is 10Å to 500Å.

The organic light emitting device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present application, that is, the compound of Formula 1 and the compound of Formula 2 .

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 application 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 formed by depositing a metal or conductive metal oxide or alloys thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. And, after forming a hole injection layer, a hole transport layer, an organic material layer including a light emitting layer and an electron transport layer, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound of Formula 1 and the compound of Formula 2 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. 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 to these.

In addition to such a 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 (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In one embodiment of the present application, 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. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO ₂ :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. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There is a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is produced in the light emitting layer. A compound which prevents migration of the excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferable. It is preferable that the HOMO (Highest Occupied Molecular Orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As a hole transport material, the hole is transported to the light emitting layer by transporting holes from the anode or the hole injection layer, and the mobility of holes is large. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in the visible region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized Styryl Compound; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

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 from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. 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.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

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

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

The preparation of the organic light emitting device including the compound of Formula 1 and the compound of Formula 2 will be described in detail in the Examples below. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited by them.

<Production Example>

<Production Example 1> Preparation of compound A

1-1) Preparation of Compound A-2

9-bromoanthracene (20.0g, 77.8mmol) and dibenzofuran-2-boronic acid (18.1g, 85.6mmol) were dissolved in 200ml of 1,4-dioxane in a 3-neck flask and K ₂ CO ₃ (12.5g, 583 mmol) was dissolved in 200 ml of H ₂ O. Pd(P(t-Bu) ₃ ) ₂ (0.40 g, 0.78 mmol) was added thereto, and the mixture was stirred for 5 hours under argon atmosphere reflux conditions. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and toluene. After the extract was dried over MgSO ₄ , filtered and concentrated, the sample was purified by silica gel column chromatography to obtain 19.6 g of Compound A-2. (Yield 73%, MS[M+H]+=345)

1-2) Preparation of Compound A-1

In a 2-neck flask, 200 ml of Compound A-2 (19.6 g, 56.9 mmol), N-bromosuccinimide (NBS) (11.1 g, 62.6 mmol) and dimethylformamide (DMF) were added, and at room temperature under argon atmosphere, 10 ml. Stir for hours. After the reaction was completed, the reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and then the sample was purified by silica gel column chromatography to obtain 18.5 g of Compound A-1. (Yield 81%, MS[M+H] ⁺ =424)

1-3) Preparation of Compound A

Compound A-1 (19.4g, 45.8mmol) and dibenzofuran-1-boronic acid (10.7g, 50.4mmol) were dissolved in 300ml of 1,4-dioxane in a 3-neck flask, and K ₂ CO ₃ (12.7g, 104mmol) ) Was dissolved in 100 ml of H ₂ O. Pd(P(t-Bu) ₃ ) ₂ (0.27 g, 0.46 mmol) was added thereto, and the mixture was stirred for 5 hours under reflux conditions under an argon atmosphere. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and toluene. After the extract was dried over MgSO ₄ , filtered and concentrated, the sample was purified by silica gel column chromatography to obtain 12.1 g of Compound A. (Yield 51%, MS[M+H] ⁺ =511)

<Production Example 2> Preparation of compound B

2-1) Preparation of compound B-2

Synthesis was performed in the same manner as in Preparation Example 1-1, except that dibenzofuran-3-boronic acid was used in Preparation Example 1-1 instead of dibenzofuran-2-boronic acid, to obtain 21.8 g of Compound B-2. (Yield 81%, MS[M+H] ⁺ =345)

2-2) Preparation of compound B-1

Synthesis was performed in the same manner as in Production Example 1-2 except that Compound B-2 was used instead of Compound A-2 in Production Example 1-2 to obtain 20.1 g of Compound B-1. (Yield 75%, MS[M+H] ⁺ =424)

2-3) Preparation of Compound B

Synthesis was performed in the same manner as in Production Example 1-3 except that Compound B-1 was used instead of Compound A-1 in Production Example 1-3 to obtain 15.1 g of Compound B. (Yield 62%, MS [M+H] ⁺ =511)

<Production Example 3> Preparation of compound C

Synthesis was performed in the same manner as in Production Example 2-3, except that dibenzofuran-2-boronic acid was used instead of dibenzofuran-1-boronic acid in Preparation Example 2-3, to obtain 10.9 g of Compound C. (Yield 45%, MS[M+H] ⁺ =511)

<Production Example 4> Preparation of compound D

4-1) Preparation of compound D-4

Three-necked flask and dissolved in 2-bromo-anthracene (50.0g, 194mmol), phenylboronic acid (26.1g, 214mmol) and 1,4-dioxane _{500ml K 2 CO 3 (53.8g,} 389mmol) of H ₂ O 200ml Melted in. Pd(P(t-Bu) ₃ ) ₂ (0.99 g, 1.9 mmol) was added thereto, and the mixture was stirred for 5 hours under an argon atmosphere reflux condition. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and toluene. After the extract was dried over MgSO ₄ , filtered and concentrated, the sample was purified by silica gel column chromatography to obtain 48.4 g of Compound D-4. (Yield 98%, MS[M+H] ⁺ =255)

4-2) Preparation of compound D-3

Synthesis was performed in the same manner as in Production Example 1-2 except that Compound D-4 was used instead of Compound A-2 in Production Example 1-2 to obtain 21.1 g of Compound D-3. (Yield 80%, MS[M+H] ⁺ =334)

4-3) Preparation of compound D-2

Synthesis was performed in the same manner as in Production Example 1-1, except that Compound D-3 in place of 9-bromoanthracene in Preparation Example 1-1 and dibenzofuran-1-boronic acid were used instead of dibenzofuran-2-boronic acid. This gave 19.3 g of compound D-2. (Yield 76%, MS [M+H] ⁺ = 421)

4-4) Preparation of compound D-1

Synthesis was performed in the same manner as in Production Example 1-2 except that Compound D-2 was used instead of Compound A-2 in Production Example 1-2 to obtain 17.1 g of Compound D-1. (Yield 72%, MS[M+H] ⁺ =500)

4-5) Preparation of compound D

Synthesis was performed in the same manner as in Preparation Example 3, except that Compound D-1 was used instead of Compound B-1 in Preparation Example 3, and 9.0 g of Compound D was obtained. (Yield 45%, MS[M+H] ⁺ =587)

<Production Example 5> Preparation of compound E

5-1) Preparation of compound E-4

Synthesis was performed in the same manner as in Production Example 4-1, except that naphthyl-1-boronic acid was used instead of phenylboronic acid in Production Example 4-1, to obtain 49.1 g of Compound E-4. (Yield 83%, MS[M+H] ⁺ =305)

5-2) Preparation of compound E-3

Synthesis was performed in the same manner as in Production Example 4-2, except that Compound E-4 was used instead of Compound D-4 in Production Example 4-2, to obtain 14.8 g of Compound E-3. (Yield 59%, MS[M+H] ⁺ =384)

5-3) Preparation of compound E-2

Synthesis was performed in the same manner as in Production Example 4-3, except that Compound E-3 was used instead of Compound D-3 in Production Example 4-3, to obtain 13.8 g of Compound E-2. (Yield 76%, MS [M+H] ⁺ =471)

5-4) Preparation of compound E-1

Synthesis was performed in the same manner as in Production Example 4-4, except that Compound E-2 was used instead of Compound D-2 in Production Example 4-4, to obtain 13.8 g of Compound E-1. (Yield 59%, MS[M+H] ⁺ =550)

5-5) Preparation of compound E

Synthesis was performed in the same manner as in Production Example 4-5, except that Compound E-1 was used instead of Compound D-1 in Production Example 4-5, and 8.4 g of Compound E was obtained. (Yield 45%, MS[M+H] ⁺ =637)

<Production Example 6> Preparation of compound F

6-1) Preparation of compound F-2

Synthesis was performed in the same manner as in Preparation Example 4-3, except that dibenzofuran-1-boronic acid was used in Preparation Example 4-3 instead of dibenzofuran-1-boronic acid, to obtain 16.9 g of Compound F-2. (Yield 67%, MS [M+H] ⁺ = 421)

6-2) Preparation of compound F-1

Synthesis was performed in the same manner as in Production Example 4-4, except that Compound F-2 was used instead of Compound D-2 in Production Example 4-4, to obtain 13.0 g of Compound F-1. (Yield 65%, MS[M+H] ⁺ =500)

6-3) Preparation of compound F

Synthesis was performed in the same manner as in Production Example 4-5, except that Compound F-1 was used instead of Compound D-1 in Preparation Example 4-5, and dibenzofuran-3-boronic acid was used instead of Dibenzofuran-2-boronic acid. 10.5 g of compound F was obtained. (Yield 69%, MS[M+H] ⁺ =587)

<Production Example 7> Preparation of compound G

7-1) Preparation of compound G-2

Synthesis was performed in the same manner as in Preparation Example 5-3, except that Dibenzofuran-1-boronic acid was used in Preparation Example 5-3 instead of dibenzofuran-1-boronic acid, to obtain 16.9 g of Compound G-2. (Yield 67%, MS [M+H] ⁺ = 421)

7-2) Preparation of compound G-1

Synthesis was performed in the same manner as in Production Example 5-4, except that Compound G-2 was used instead of Compound E-2 in Production Example 5-4, to obtain 13.0 g of Compound G-1. (Yield 65%, MS[M+H] ⁺ =500)

7-3) Preparation of compound G

Synthesis was performed in the same manner as in Production Example 5-5, except that Compound G-1 was used instead of Compound E-1 in Preparation Example 5-5, and dibenzofuran-3-boronic acid was used instead of Dibenzofuran-2-boronic acid. 10.5 g of compound G was obtained. (Yield 69%, MS[M+H] ⁺ =587)

<Production Example 8> Preparation of compound H

8-1) Preparation of compound H-1

Synthesis was performed in the same manner as in Production Example 1-3, except that dibenzofuran-1-boronic acid was used in Preparation Example 1-3 instead of dibenzofuran-1-boronic acid, to obtain 11.3 g of Compound H-1. (Yield 56%, MS[M+H] ⁺ =511)

8-2) Preparation of compound H

Compound H-1 (10 g) and AlCl ₃ (2 g) were added to C ₆ D ₆ (150 ml) and stirred for 2 hours. After the completion of the reaction, D ₂ O (25 ml) was added, stirred for 30 minutes, and trimethylamine (3 ml) was added dropwise. The reaction solution was transferred to a separatory funnel, and extracted with water and toluene. After drying the extract with MgSO ₄ , recrystallization with ethyl acetate gave 8.8 g of compound H. (Yield 84%, MS[M+H] ⁺ =533)

<Production Example 9> Preparation of compound BD-A

9-1) Preparation of compound BD-A-2

1,2,3-Tribromo-5-chlorobenzene (5 g), bis-(4-(tert-butyl)phenyl)amine (8 g), Pd (P-tBu ₃ ) ₂ (0.15 g) ), NaOBu (4.1 g) was dissolved in 50 ml of xylene and stirred for 3 hours. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and toluene. The extract was dried with MgSO ₄ , filtered and concentrated, and then purified by recrystallization (ethyl acetate/hexane) to obtain 7.2 g of compound BD-A-2. (Yield 67%, MS[M+H] ⁺ =751)

9-2) Preparation of compound BD-A-1

To a flask containing compound BD-A-2 (7.2 g) and xylene (100 ml), n-butyllithium pentane solution (8 ml, 2.5 M in hexane) was added dropwise at 0° C. under an argon atmosphere. After completion of dropping, the mixture was heated to 50°C and stirred for 2 hours. After cooling to -40°C, boron tribromide (2.80ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, it was cooled to 0°C again, N,N-isopropylethylamine (8 ml) was added, and the reaction solution was further stirred at room temperature for 30 minutes. After adding NaCl saturated solution and ethyl acetate and separating, the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography gave 1.5 g of compound BD-A-1. (Yield 23%, MS[M+H] ⁺ =680)

9-3) Preparation of compound BD-A

Compound BD-A-1 (1.5 g), diphenylamine (0.42 g), Pd(P-tBu ₃ ) ₂ (25 mg), CsCO ₃ (2.2 g) were dissolved in 20 ml of xylene and stirred at 130° C. for 2 hours. Did. After the reaction solution was cooled to room temperature, NH ₄ Cl saturated solution and toluene were added to separate the solution, and the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography gave 1.2 g of compound BD-A. (Yield 67%, MS[M+H] ⁺ =812)

<Production Example 10> Preparation of compound M

10-1) Preparation of compound M-2

Synthesis was performed in the same manner as in Production Example 1-1, except that dibenzothiophene-2-boronic acid was used instead of dibenzofuran-2-boronic acid in Production Example 1-1 to obtain 45.1 g of Compound M-2. . (Yield 64%, MS[M+H] ⁺ =361)

10-2) Preparation of compound M-1

Synthesis was performed in the same manner as in Production Example 1-2 except that Compound M-2 was used instead of Compound A-2 in Production Example 1-2 to obtain 19.9 g of Compound M-1. (Yield 82%, MS[M+H] ⁺ =440)

10-3) Preparation of compound M

Synthesis was performed in the same manner as in Production Example 1-3, except that Compound M-1 was used instead of Compound A-1 in Preparation Example 1-3 and dibenzothiophene-1-boronic acid was used instead of Dibenzofuran-1-boronic acid. This gave 12.1 g of compound M. (Yield 49%, MS[M+H] ⁺ =543)

<Production Example 11> Preparation of compound N

11-1) Preparation of compound N-2

Synthesis was performed in the same manner as in Production Example 1-1, except that dibenzothiophene-3-boronic acid was used instead of dibenzofuran-2-boronic acid in Production Example 1-1 to obtain 46.5 g of Compound N-2. . (Yield 66%, MS[M+H] ⁺ =361)

11-2) Preparation of compound N-1

Synthesis was performed in the same manner as in Production Example 1-2 except that Compound N-2 was used instead of Compound A-2 in Production Example 1-2 to obtain 20.8 g of Compound N-1. (Yield 85%, MS[M+H] ⁺ =440)

11-3) Preparation of compound N

Synthesis was performed in the same manner as in Preparation Example 1-3, except that Compound N-1 was used instead of Compound A-1 in Preparation Example 1-3 and dibenzothiophene-1-boronic acid was used instead of Dibenzofuran-1-boronic acid. This gave 13.4 g of compound N. (Yield 54%, MS[M+H] ⁺ =543)

<Production Example 12> Preparation of compound O

In Preparation Example 11-3, dibenzothiophene-1-boronic acid was used instead of dibenzothiophene-2-boronic acid, and synthesis was performed in the same manner as in Preparation Example 11-3 to obtain 12.4 g of Compound O. (Yield 50%, MS[M+H]+=543)

<Production Example 13> Preparation of compound P

13-1) Preparation of compound P-2

In Preparation Example 4-3, dibenzothiophene-1-boronic acid was used instead of dibenzofuran-1-boronic acid, and synthesis was performed in the same manner as in Preparation Example 4-3 to obtain 17.6 g of Compound P-2. . (Yield 67%, MS[M+H] ⁺ =437)

13-2) Preparation of compound P-1

Synthesis was performed in the same manner as in Production Example 4-4, except that Compound P-2 was used instead of Compound D-2 in Production Example 4-4, and 18.8 g of Compound P-1 was obtained. (Yield 80%, MS[M+H] ⁺ =440)

13-3) Preparation of compound P

Synthesis was performed in the same manner as in Preparation Example 4-5, except that Compound P-1 was used instead of Compound D-1 in Preparation Example 4-5, and dibenzothiophene-2-boronic acid was used instead of Dibenzofuran-2-boronic acid. This gave 10.2 g of compound P. (Yield 42%, MS[M+H] ⁺ =619)

<Production Example 14> Preparation of compound Q

In Preparation Example 13-3, dibenzothiophene-2-boronic acid was used instead of dibenzothiophene-3-boronic acid, and synthesis was performed in the same manner as in Preparation Example 13-3 to obtain 11.9 g of Compound Q. (Yield 49%, MS[M+H] ⁺ =619)

<Production Example 15> Preparation of compound R

15-1) Preparation of compound R-2

In Preparation Example 4-3, instead of dibenzofuran-1-boronic acid, dibenzothiophene-2-boronic acid was used, and synthesis was performed in the same manner as in Preparation Example 4-3 to obtain 18.8 g of Compound R-2. . (Yield 72%, MS[M+H] ⁺ =437)

15-2) Preparation of compound R-1

Synthesis was performed in the same manner as in Production Example 4-4, except that Compound R-2 was used instead of Compound D-2 in Production Example 4-4, to obtain 19.6 g of Compound R-1. (Yield 83%, MS[M+H] ⁺ =440)

15-3) Preparation of compound R

Synthesis was performed in the same manner as in Production Example 4-5, except that Compound R-1 was used instead of Compound D-1 in Preparation Example 4-5, and dibenzothiophene-3-boronic acid was used instead of Dibenzofuran-2-boronic acid. This gave 11.4 g of compound R. (Yield 47%, MS[M+H] ⁺ =619)

<Experimental Example>

<Experimental Example 1> Examples 1 to 8 and Comparative Examples 1 to 7

The glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 150 nm was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as the detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as the 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. Further, the substrate was washed for 5 minutes using nitrogen plasma, and then transferred to a vacuum evaporator.

The HAT-CN compound below was thermally vacuum-deposited to a thickness of 5 nm on the prepared ITO transparent electrode to form a hole injection layer. Subsequently, HTL1 was thermally vacuum-deposited to a thickness of 100 nm, and then HTL2 was thermally vacuum-deposited to a thickness of 10 nm to form a hole transport layer. Subsequently, as a host and a dopant, the compounds shown in Table 1 below were simultaneously vacuum-deposited in a weight ratio of 95:5 to form a 20 nm-thick light emitting layer. Subsequently, ETL was vacuum deposited to a thickness of 20 nm to form an electron transport layer. Subsequently, LiF was vacuum deposited to a thickness of 0.5 nm to form an electron injection layer. Subsequently, aluminum was deposited to a thickness of 100 nm to form a cathode to prepare an organic light emitting device.

The driving voltage, luminous efficiency, color coordinates, and lifetime measured at a current density of 10 mA/cm ² of the organic light emitting devices manufactured in Examples 1 to 8 and Comparative Examples 1 to 7 are shown in Table 1 below.

	Host	Dopant	10 mA/cm 2 measured value				Life Span (T 97 )
			Driving voltage (V OP )	Luminous efficiency (Cd/A)	Color coordinate
					CIE_x	CIE_y
Example 1	A	BD-A	3.57	8.38	0.137	0.107	115
Example 2	B	BD-A	3.46	8.25	0.137	0.107	126
Example 3	C	BD-A	3.66	8.25	0.137	0.108	130
Example 4	D	BD-A	3.31	8.11	0.138	0.113	133
Example 5	E	BD-A	3.70	8.44	0.138	0.116	135
Example 6	F	BD-A	3.46	8.08	0.138	0.110	135
Example 7	G	BD-A	3.50	8.14	0.137	0.115	140
Example 8	H	BD-A	3.48	8.32	0.137	0.106	165
Comparative Example 1	I	BD-A	3.55	8.01	0.137	0.106	103
Comparative Example 2	J	BD-A	3.73	7.88	0.137	0.105	130
Comparative Example 3	K	BD-A	3.89	7.90	0.137	0.108	90
Comparative Example 4	L	BD-A	3.70	7.92	0.137	0.112	96
Comparative Example 5	A	BD-B	3.65	7.41	0.137	0.110	105
Comparative Example 6	D	BD-B	3.36	7.30	0.137	0.116	131
Comparative Example 7	F	BD-B	3.49	7.24	0.138	0.115	128

<Experimental Example 2> Examples 9 to 14 and Comparative Examples 8 to 11

Prepared in the same manner as in Experimental Example 1, the organic light emitting device was manufactured using the compound shown in Table 2 as a host and a dopant, 10 of the organic light emitting device prepared in Examples 9 to 14 and Comparative Examples 8 to 11 to a driving voltage, luminous efficiency, color coordinates and lifespan measured at a current density mA / cm ² are shown in Table 2 below.

	Host	Dopant	10 mA/cm 2 measured value				Life Span (T 97 )
			Driving voltage (V OP )	Luminous efficiency (Cd/A)	Color coordinate
					CIE_x	CIE_y
Example 9	M	BD-A	3.50	8.17	0.137	0.111	115
Example 10	N	BD-A	3.57	8.09	0.137	0.110	110
Example 11	O	BD-A	3.39	8.35	0.137	0.112	125
Example 12	P	BD-A	3.51	8.15	0.137	0.114	120
Example 13	Q	BD-A	3.53	8.14	0.137	0.112	120
Example 14	R	BD-A	3.31	8.42	0.137	0.115	135
Comparative Example 8	S	BD-A	3.61	8.04	0.137	0.109	90
Comparative Example 9	M	BD-B	3.53	7.24	0.138	0.112	112
Comparative Example 10	N	BD-B	3.65	7.19	0.137	0.110	105
Comparative Example 11	Q	BD-B	3.60	7.21	0.137	0.111	114

As shown in Tables 1 and 2, the organic light emitting devices of Examples 1 to 14 including the compound of Formula 1 and the compound of Formula 2, respectively, as the dopant and host of the light emitting layer include the compound of Formula 1 as a dopant, but the host As a result, it was found that the organic light-emitting devices of Comparative Examples 1 to 4 and Comparative Example 8 containing the conventional anthracene derivative compound were superior in driving voltage, luminous efficiency, and/or life. In addition, the organic light emitting device according to the present invention than the organic light emitting device of Comparative Examples 5 to 7 and Comparative Examples 9 to 11 containing a compound of Formula 2 as a host but not a compound of Formula 1 as a dopant is the driving voltage. , It can be confirmed that it is excellent in luminous efficiency and/or life.

Specifically, in the case of the compound of Formula 2 of the present invention, by introducing dibenzofuran and/or dibenzothiophene into the anthracene core structure, electron transport ability increases, thereby lowering the driving voltage and external quantum efficiency. Will increase.

Although the preferred experimental example of the present invention has been described through the above, the present invention is not limited to this, and it is possible to carry out various modifications within the scope of the claims and the detailed description of the invention, and this also belongs to the scope of the invention. .

Claims (11)

1. 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,

   At least one layer of the organic material layer is an organic light emitting device comprising a compound of Formula 1 and a compound of Formula 2:

   [Formula 1]

   

   In Chemical Formula 1,

   A, B and C are each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted heterocycle,

   X3 and X4 are each independently O; S; Or NR,

   Y1 is boron or phosphine oxide,

   R is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

   The adjacent groups among R, A, B and C may combine with each other to form a ring,

   [Formula 2]

   

   In Chemical Formula 2,

   X1 and X2 are each independently O or S,

   R1 to R3 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

   a and b are each independently an integer from 0 to 7,

   c is an integer from 0 to 8,

   When a to c are each independently an integer of 2 or more, the substituents in parentheses are the same or different from each other.
2. The method according to claim 1,

   The formula 1 is an organic light emitting device represented by the following formula 1-1:

   [Formula 1-1]

   

   In Formula 1-1, the definitions of A, B, C and Y1 are the same as those in Formula 1,

   R'and R" are each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryl group Or a substituted or unsubstituted heterocyclic group,

   R', R", A, B and C adjacent groups may combine with each other to form a ring.
3. The method according to claim 1,

   The formula 1 is an organic light emitting device represented by the following formula 1-2:

   [Formula 1-2]

   

   In Chemical Formula 1-2,

   The definitions of A, B and C are the same as those in formula (1),

   R'and R" are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

   R', R", B and C adjacent groups may combine with each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic group.
4. The method according to claim 1,

   The A, B and C are each independently, substituted or unsubstituted benzene; Substituted or unsubstituted naphthalene; Or dibenzofuran.
5. The method according to claim 1,

   R is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.
6. The method according to claim 1,

   R1 to R3 are each independently hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with deuterium; Or an organic light emitting device that is a naphthyl group.
7. The method according to claim 1,

   Formula 1 is an organic light emitting device is selected from the following structural formula:

   

   

   .
8. The method according to claim 1,

   Formula 2 is an organic light emitting device is selected from the following structural formula:

   

   

   

   

   

   

   .
9. The method according to claim 1,

   The organic light emitting device of the one or more organic material layer includes a light emitting layer, the light emitting layer comprises a compound of Formula 1 and a compound of Formula 2.
10. The method according to claim 9,

    The light emitting layer is an organic light emitting device comprising the compound of Formula 1 as a dopant material, and the compound of Formula 2 as a host material.
11. The method according to claim 10,

    The weight ratio of the compound of Formula 1 and the compound of Formula 2 is 1:99 to 10:90.

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