KR20210107594A - Organic light emitting device - Google Patents

Abstract

The present specification provides an organic light emitting device that 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. At least one layer of the organic material layer includes the compound of chemical formula 1 and the compound of chemical formula 2.

Description

Organic light emitting device {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 by reference.

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.

The development of new materials for the organic light emitting device as described above is continuously required.

Korean Patent Publication No. 10-2016-087331

An object of the present application is to provide an organic light emitting device.

The present application relates to 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 provides an organic light emitting device including the compound of Formula 1 and the compound of Formula 2 below.

[Formula 1]

In Formula 1,

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

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,

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

[Formula 2]

In 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 of 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 as or different from each other.

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

1 illustrates 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.
Figure 2 is a 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) are sequentially An example of an organic light-emitting device stacked with

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 above.

Examples of substituents in the present specification are described below, but are not limited thereto.

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl 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 it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in 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 linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 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.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and 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, etc., but are not limited thereto. does not

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. 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. may be, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, 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, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the amine group is -NH ₂ ; an alkylamine group; N-alkylarylamine group; arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; naphthylamine group; biphenylamine group; anthracenylamine group; 9-methylanthracenylamine group; diphenylamine group; N-phenylnaphthylamine group; ditolylamine group; N-phenyltolylamine group; triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine 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; propyldimethylsilyl group; triphenylsilyl group; diphenylsilyl group; There is a phenylsilyl group, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl 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 C10-C24. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a 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.

,

,

및

등이 될 수 있으나, 이에 한정되는 것은 아니다.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 atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. Although the number of carbon atoms of the heterocyclic group is not particularly limited, it is preferably from 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

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

In the present specification, the description of the above-described heterocyclic group may be applied, except that the heterocyclic group is a divalent group.

In the present specification, the meaning of forming a ring by bonding with adjacent groups means a substituted or unsubstituted hydrocarbon ring by bonding with adjacent groups; And a substituted or unsubstituted heterocycle is formed, and the hydrocarbon ring and the heterocycle may be aliphatic, aromatic, or condensed forms thereof, but are not limited thereto.

In the present specification, the aliphatic hydrocarbon ring refers to a ring made of only carbon and hydrogen atoms as a non-aromatic ring.

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

In the present specification, the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms.

In the present specification, the aromatic heterocycle refers to an aromatic ring including one or more heteroatoms.

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

In the present specification, when adjacent groups combine with each other to form a ring, adjacent groups may combine 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 of 0 to 4,

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

* indicates the position to be substituted.

As used herein, "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. can For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

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 heterocyclic ring.

In addition, according to an exemplary embodiment of the present application, the 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 heterocyclic ring 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 heterocyclic ring having 3 to 30 carbon atoms.

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

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

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

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

According to an exemplary embodiment of the present application, C is 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 are O.

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

Also, 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 be bonded to 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 heterocycle, and aliphatic, aromatic or their It may be in a condensed form.

Also, according to an exemplary embodiment of the present application, adjacent groups among 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 heterocycle having 2 to 60 carbon atoms. and may be in the form of aliphatic, aromatic or condensed forms thereof.

In addition, according to an exemplary embodiment of the present application, adjacent groups of 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 in the form of aliphatic, aromatic or condensed forms thereof.

According to an exemplary embodiment of the present application, Chemical Formula 1 may be represented by the following Chemical 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,

Adjacent groups among R′, R″, A, B and C may be bonded to 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.

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

Also, 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.

Also, according to an exemplary embodiment of the present application, R' and R" are each independently 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', 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 heterocycle, aliphatic, It may be in 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 2 to 60 It may form a heterocycle, and may be in 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 a substituted or unsubstituted C6 to C30 hydrocarbon ring or a substituted or unsubstituted C2 to C30 It may form a heterocycle, and may be in an aliphatic, aromatic or condensed form thereof.

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

[Formula 1-2]

In 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,

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 heterocycle, and may be aliphatic, aromatic, or condensed forms 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 in aliphatic, aromatic or condensed forms 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 a substituted or unsubstituted C6 to C30 hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocycle may be formed, and may be in an aliphatic, aromatic or condensed form thereof.

Also, according to an exemplary 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, Chemical Formula 1 is selected from the following structural formulas.

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 are O.

According to an exemplary embodiment of the present application, X1 and X2 are 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 C6-C60 aryl group.

According to an exemplary embodiment of the present application, R1 to R3 are each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C6-C30 aryl group.

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, and 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 an exemplary embodiment of the present application, R1 and R2 are a phenyl group, 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, and R3 is deuterium.

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

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

According to an exemplary 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 of 1 to 7, an integer of 3 to 7, an integer of 5 to 7, or an integer of 6 to 7.

According to an exemplary embodiment of the present application, when R2 is deuterium, b may be an integer of 1 to 7, an integer of 3 to 7, an integer of 5 to 7, or an integer of 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, or 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, Chemical Formula 2 is selected from the following structural formulas.

In the present application, when a member is said to be located "on" another member, this includes not only a case in which a member is in contact with another member but also a case in which another member is present between the two members.

In the present application, when a part "includes" a certain component, this means that other components may be further included, rather than excluding 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, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In an exemplary embodiment of the present application, the organic light emitting device further comprises one 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 an exemplary embodiment of the present application, the organic light emitting device includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1 and the compound of Formula 2 above.

In an exemplary embodiment of the present application, the one 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 for simultaneously transporting and injecting holes, 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 the compound of Formula 1 and the compound of Formula 2 above.

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

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

In another exemplary embodiment, the organic light emitting device may be a normal type organic light emitting device 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 diode according to an 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 such a structure, the compound of Formula 1 and the compound of Formula 2 may be included in the emission layer 3 .

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

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

The organic light emitting device of the present application may be manufactured using 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 may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. 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 of Formula 1 and the compound of Formula 2 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 coating method refers to 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 manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Laid-Open No. 2003/012890). However, the manufacturing method is not limited thereto.

In the exemplary 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.

As the anode material, a material having a large work function is generally preferable to facilitate hole injection into the organic material layer. Specific examples of the anode 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); combinations of metals and oxides 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 the 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; and 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 the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film 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 material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, 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. material is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. do. Specific examples include Al complex of 8-hydroxyquinoline; complexes comprising Alq3; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer. A compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The hole blocking layer is a layer that blocks the holes from reaching the cathode, 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 is not limited thereto.

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

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 Examples below. However, the following examples are for illustrative purposes only, and the scope of the present specification is not limited thereto.

<Production Example>

<Preparation Example 1> Preparation of compound A

1-1) Preparation of compound A-2

Dissolve 9-bromoanthracene (20.0 g, 77.8 mmol) and dibenzofuran-2-boronic acid (18.1 g, 85.6 mmol) in 1,4-dioxane 200 ml in a three-necked flask, K ₂ CO ₃ (12.5 g, 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 reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and toluene. After drying the extract with MgSO ₄ , filtration and concentration, 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

Compound A-2 (19.6g, 56.9mmol), N-bromosuccinimide (NBS) (11.1g, 62.6mmol) and 200ml of dimethylformamide (DMF) were put in a two-neck flask, and 10 at room temperature under an argon atmosphere. time was stirred. After completion of the reaction, 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 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 (19.4 g, 45.8 mmol) and dibenzofuran-1-boronic acid (10.7 g, 50.4 mmol) were dissolved in 300 ml of 1,4-dioxane in a three-necked flask, and K ₂ CO ₃ (12.7 g, 104 mmol) ) 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 in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and toluene. After drying the extract with MgSO ₄ , filtration and concentration, the sample was purified by silica gel column chromatography to obtain 12.1 g of Compound A. (Yield 51%, MS[M+H] ⁺ =511)

<Preparation Example 2> Preparation of compound B

2-1) Preparation of compound B-2

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

2-2) Preparation of compound B-1

20.1 g of Compound B-1 was obtained by performing the synthesis in the same manner as in Preparation Example 1-2, except that Compound B-2 was used instead of Compound A-2 in Preparation Example 1-2. (yield 75%, MS[M+H] ⁺ =424)

2-3) Preparation of compound B

15.1 g of Compound B was obtained by performing the synthesis in the same manner as in Preparation Example 1-3, except that Compound B-1 was used instead of Compound A-1 in Preparation Example 1-3. (Yield 62%, MS[M+H] ⁺ =511)

<Preparation Example 3> Preparation of compound C

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

<Preparation Example 4> Preparation of compound D

4-1) Preparation of compound D-4

Dissolve 2-bromoanthracene (50.0 g, 194 mmol) and phenylboronic acid (26.1 g, 214 mmol) in 500 ml of 1,4-dioxane in a 3-neck flask, and K ₂ CO ₃ (53.8 g, 389 mmol) in H ₂ O 200 ml 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 reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and toluene. After drying the extract with MgSO ₄ , filtration and concentration, 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

21.1 g of Compound D-3 was obtained by performing the synthesis in the same manner as in Preparation Example 1-2, except that Compound D-4 was used instead of Compound A-2 in Preparation Example 1-2. (yield 80%, MS[M+H] ⁺ =334)

4-3) Preparation of compound D-2

In Preparation Example 1-1, the synthesis was carried out in the same manner as in Preparation Example 1-1, except that compound D-3 instead of 9-bromoanthracene and dibenzofuran-1-boronic acid instead of dibenzofuran-2-boronic acid were used. Thus, 19.3 g of compound D-2 was obtained. (Yield 76%, MS[M+H] ⁺ =421)

4-4) Preparation of compound D-1

17.1 g of Compound D-1 was obtained by performing the synthesis in the same manner as in Preparation Example 1-2, except that Compound D-2 was used instead of Compound A-2 in Preparation Example 1-2. (Yield 72%, MS[M+H] ⁺ =500)

4-5) Preparation of compound D

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

<Preparation Example 5> Preparation of compound E

5-1) Preparation of compound E-4

Synthesis was carried out in the same manner as in Preparation Example 4-1, except that naphthyl-1-boronic acid was used instead of phenylboronic acid in Preparation 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

In Preparation Example 4-2, 14.8 g of Compound E-3 was obtained by performing the synthesis in the same manner as in Preparation Example 4-2, except that Compound E-4 was used instead of Compound D-4. (yield 59%, MS[M+H] ⁺ =384)

5-3) Preparation of compound E-2

13.8 g of compound E-2 was obtained in the same manner as in Preparation Example 4-3, except that Compound E-3 was used instead of Compound D-3 in Preparation Example 4-3. (yield 76%, MS[M+H] ⁺ =471)

5-4) Preparation of compound E-1

13.8 g of Compound E-1 was obtained in the same manner as in Preparation Example 4-4, except that Compound E-2 was used instead of Compound D-2 in Preparation Example 4-4. (yield 59%, MS[M+H] ⁺ =550)

5-5) Preparation of compound E

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

<Preparation Example 6> Preparation of compound F

6-1) Preparation of compound F-2

In Preparation Example 4-3, 16.9 g of compound F-2 was obtained by performing the synthesis in the same manner as in Preparation Example 4-3, except that dibenzofuran-2-boronic acid was used instead of dibenzofuran-1-boronic acid. (Yield 67%, MS[M+H] ⁺ =421)

6-2) Preparation of compound F-1

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

6-3) Preparation of compound F

In Preparation Example 4-5, the synthesis was carried out in the same manner as in Preparation Example 4-5, except that compound F-1 instead of compound D-1 and dibenzofuran-3-boronic acid instead of dibenzofuran-2-boronic acid were used. 10.5 g of compound F was obtained. (yield 69%, MS[M+H] ⁺ =587)

<Preparation Example 7> Preparation of compound G

7-1) Preparation of compound G-2

16.9 g of compound G-2 was obtained by performing the synthesis in the same manner as in Preparation Example 5-3, except that dibenzofuran-2-boronic acid was used instead of dibenzofuran-1-boronic acid in Preparation Example 5-3. (Yield 67%, MS[M+H] ⁺ =421)

7-2) Preparation of compound G-1

13.0 g of compound G-1 was obtained by performing the synthesis in the same manner as in Preparation Example 5-4, except that Compound G-2 was used instead of Compound E-2 in Preparation Example 5-4. (Yield 65%, MS[M+H] ⁺ =500)

7-3) Preparation of compound G

In Preparation Example 5-5, the synthesis was carried out in the same manner as in Preparation Example 5-5, except that compound G-1 instead of compound E-1 and dibenzofuran-3-boronic acid instead of dibenzofuran-2-boronic acid were used. 10.5 g of compound G was obtained. (yield 69%, MS[M+H] ⁺ =587)

<Preparation Example 8> Preparation of compound H

8-1) Preparation of compound H-1

11.3 g of Compound H-1 was obtained in the same manner as in Preparation Example 1-3, except that dibenzofuran-2-boronic acid was used instead of dibenzofuran-1-boronic acid in Preparation Example 1-3. (Yield 56%, MS[M+H] ⁺ =511)

8-2) Preparation of compound H

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

<Preparation 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) in a 3-neck flask ), NaOBu (4.1 g) was dissolved in 50 ml of xylene and stirred for 3 hours. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and toluene. The extract _{was dried over 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 the flask containing the 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 the dropwise addition, the temperature was raised to 50° C. and stirred for 2 hours. After cooling to -40°C, boron tribromide (2.80 ml) was added, the temperature was raised to room temperature, and the mixture was stirred for 4 hours. After that, 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 separation by adding saturated NaCl solution and ethyl acetate, 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), and 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, a _{saturated NH 4} Cl solution and toluene were added to separate the mixture, and the solvent was distilled off under reduced pressure. It was purified by silica gel column chromatography to obtain 1.2 g of compound BD-A. (Yield 67%, MS[M+H] ⁺ =812)

<Preparation Example 10> Preparation of compound M

10-1) Preparation of compound M-2

The synthesis was performed in the same manner as in Preparation Example 1-1, except that dibenzothiophene-2-boronic acid was used instead of dibenzofuran-2-boronic acid in Preparation 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

19.9 g of compound M-1 was obtained by performing the synthesis in the same manner as in Preparation Example 1-2, except that Compound M-2 was used instead of Compound A-2 in Preparation Example 1-2. (Yield 82%, MS[M+H] ⁺ =440)

10-3) Preparation of compound M

In Preparation Example 1-3, the synthesis was carried out in the same manner as in Preparation Example 1-3, except that Compound M-1 instead of Compound A-1 and dibenzothiophene-1-boronic acid instead of dibenzofuran-1-boronic acid were used. Thus, 12.1 g of compound M was obtained. (Yield 49%, MS[M+H] ⁺ =543)

<Preparation Example 11> Preparation of compound N

11-1) Preparation of compound N-2

In Preparation Example 1-1, except for using dibenzothiophene-3-boronic acid instead of dibenzofuran-2-boronic acid, the synthesis was performed in the same manner as in Preparation 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

In Preparation Example 1-2, 20.8 g of Compound N-1 was obtained by performing the synthesis in the same manner as in Preparation Example 1-2, except that Compound N-2 was used instead of Compound A-2. (yield 85%, MS[M+H] ⁺ =440)

11-3) Preparation of compound N

In Preparation Example 1-3, the synthesis was carried out in the same manner as in Preparation Example 1-3, except for using Compound N-1 instead of Compound A-1 and dibenzothiophene-1-boronic acid instead of dibenzofuran-1-boronic acid. 13.4 g of compound N was obtained. (Yield 54%, MS[M+H] ⁺ =543)

<Preparation Example 12> Preparation of compound O

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

<Preparation Example 13> Preparation of compound P

13-1) Preparation of compound P-2

In Preparation Example 4-3, 17.6 g of compound P-2 was obtained by performing the synthesis in the same manner as in Preparation Example 4-3, except that dibenzothiophene-1-boronic acid was used instead of dibenzofuran-1-boronic acid. . (Yield 67%, MS[M+H] ⁺ =437)

13-2) Preparation of compound P-1

18.8 g of compound P-1 was obtained by performing the synthesis in the same manner as in Preparation Example 4-4, except that Compound P-2 was used instead of Compound D-2 in Preparation Example 4-4. (yield 80%, MS[M+H] ⁺ =440)

13-3) Preparation of compound P

In Preparation Example 4-5, the synthesis was carried out in the same manner as in Preparation Example 4-5, except that compound P-1 instead of compound D-1 and dibenzothiophene-2-boronic acid instead of dibenzofuran-2-boronic acid were used. 10.2 g of compound P was obtained. (Yield 42%, MS[M+H] ⁺ =619)

<Preparation Example 14> Preparation of compound Q

In Preparation Example 13-3, 11.9 g of compound Q was obtained by performing the synthesis in the same manner as in Preparation Example 13-3, except that dibenzothiophene-3-boronic acid was used instead of dibenzothiophene-2-boronic acid. (Yield 49%, MS[M+H] ⁺ =619)

<Preparation Example 15> Preparation of compound R

15-1) Preparation of compound R-2

In Preparation Example 4-3, 18.8 g of compound R-2 was obtained by performing the synthesis in the same manner as in Preparation Example 4-3, except that dibenzothiophene-2-boronic acid was used instead of dibenzofuran-1-boronic acid. . (Yield 72%, MS[M+H] ⁺ =437)

15-2) Preparation of compound R-1

In Preparation Example 4-4, 19.6 g of Compound R-1 was obtained by performing the synthesis in the same manner as in Preparation Example 4-4, except that Compound R-2 was used instead of Compound D-2. (Yield 83%, MS[M+H] ⁺ =440)

15-3) Preparation of compound R

In Preparation Example 4-5, the synthesis was carried out in the same manner as in Preparation Example 4-5, except that compound R-1 instead of compound D-1 and dibenzothiophene-3-boronic acid instead of dibenzofuran-2-boronic acid were used. 11.4 g of compound R was obtained. (Yield 47%, MS[M+H] ⁺ =619)

<Experimental example>

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

A glass substrate coated with ITO (Indium Tin Oxide) to a thickness of 150 nm was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. In this case, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using nitrogen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermal vacuum deposition of the HAT-CN compound to a thickness of 5 nm on the prepared ITO transparent electrode. Then, 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. Then, as a host and a dopant, the compounds shown in Table 1 were simultaneously vacuum-deposited at a weight ratio of 95:5 to form a light emitting layer having a thickness of 20 nm. Then, ETL was vacuum-deposited to a thickness of 20 nm to form an electron transport layer. Then, LiF was vacuum-deposited to a thickness of 0.5 nm to form an electron injection layer. Then, aluminum was deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic light emitting diode.

The driving voltage, luminous efficiency, color coordinates, and lifetime measured at a current density ^{of 10 mA/cm 2} of the organic light emitting diodes prepared 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 ) drive voltage
(V _OP ) Luminous Efficiency
(Cd/A) color coordinates 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

10 of the organic light emitting devices prepared in Examples 9 to 14 and Comparative Examples 8 to 11 were prepared in the same manner as in Experimental Example 1, but using the compounds shown in Table 2 below as hosts and dopants. 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 ) drive voltage
(V _OP ) Luminous Efficiency
(Cd/A) color coordinates 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 above, the organic light emitting devices of Examples 1 to 14 each including the compound of Formula 1 and the compound of Formula 2 as a dopant and a 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 device of Comparative Examples 1 to 4 and Comparative Example 8 including the conventional anthracene derivative compound was superior in driving voltage, luminous efficiency and/or lifespan. In addition, the organic light emitting device according to the present invention has a driving voltage higher than that of the organic light emitting devices of Comparative Examples 5 to 7 and Comparative Examples 9 to 11 including a compound of Formula 2 as a host but not a compound of Formula 1 as a dopant. , it can be confirmed that it is excellent in luminous efficiency and/or lifetime.

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

Although preferred experimental examples of the present invention have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and detailed description of the invention, and this also falls within the scope of the invention. .

1: substrate
2: Anode
3: light emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: electron transport layer
8: electron injection layer

Claims (11)

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 Formula 1,
A, B and C are each independently, a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic ring,
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,
Adjacent groups among R, A, B and C may combine with each other to form a ring,
[Formula 2]

In 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 of 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 as or different from each other. The method according to claim 1,
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,
Adjacent groups among R′, R″, A, B and C may be bonded to each other to form a ring. The method according to claim 1,
Formula 1 is an organic light emitting device represented by the following Formula 1-2:
[Formula 1-2]

In 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,
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 heterocyclic group. The method according to claim 1,
A, B and C are each independently, substituted or unsubstituted benzene; substituted or unsubstituted naphthalene; Or an organic light emitting device that is dibenzofuran. The method according to claim 1,
R is a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group. The method according to claim 1,
wherein R1 to R3 are each independently hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with deuterium; or a naphthyl group. The method according to claim 1,
Formula 1 is an organic light emitting device selected from the following structural formulas:

. The method according to claim 1,
Formula 2 is an organic light emitting device selected from the following structural formulas:

. The method according to claim 1,
The at least one organic material layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1 and the compound of Formula 2 above. 10. The method of claim 9,
The light emitting layer includes the compound of Formula 1 as a dopant material, and the compound of Formula 2 as a host material. 11. The method of claim 10,
The weight ratio of the compound of Formula 1 to the compound of Formula 2 is 1:99 to 10:90 of the organic light emitting device.

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