KR20200070141A - Organic light emitting device - Google Patents

Abstract

The present application relates to an organic light emitting device. 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. Therefore, low driving voltage, high luminous efficiency and/or long lifespan are possible.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

The present invention claims the benefit of the filing date of Korean Patent Application No. 10-2018-0156860, filed with the Korean Patent Office on December 7, 2018, the entire contents of which are incorporated herein.

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.

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 formed of a multi-layered structure composed of different materials, for example, it 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 glows.

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

This specification is to provide an organic light emitting device.

This specification is an anode; A cathode provided opposite the anode; An emission layer provided between the anode and the cathode and including a compound represented by the following Chemical Formula 1; A hole transport region provided between the anode and the emission layer; And an electron transport region provided between the cathode and the light emitting layer and including a compound represented by Formula 2 below.

[Formula 1]

In Formula 1, A, B and C are each independently a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle, X1 and X2 are each independently O, CR1R2 or NR3, and R1 to R3 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl group, substituted Or an unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and adjacent groups among R1 to R3, A, B, and C are bonded to each other and substituted Or may form an unsubstituted ring,

[Formula 2]

In Formula 2, at least two of X4 to X6 are N and the rest are CH, and Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, L is a substituted or unsubstituted trivalent aryl group; Or a substituted or unsubstituted trivalent heterocyclic group, Y is a substituted or unsubstituted polycyclic aryl group, n is 2, and when n is 2, the two Ys 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 hole transport region 10, a light emitting layer 3, an electron transport region 20, and a cathode 4 are sequentially stacked. .
2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron regulating layer 7, an electron injection and transport layer 8, and a cathode 4 An example of this sequentially stacked organic light emitting device is shown.
3 is an MS spectrum of Compound 2-1 according to an exemplary embodiment of the present specification.
4 is an MS spectrum of Compound 2-2 according to an exemplary embodiment of the present specification.
5 is an MS spectrum of Compound 2-3 according to an exemplary embodiment of the present specification.
6 is an MS spectrum of Compound 2-4 according to an exemplary embodiment of the present specification.
7 is an MS spectrum of Compound 2-5 according to an exemplary embodiment of the present specification.
8 is an MS spectrum of Compound 2-6 according to an exemplary embodiment of the present specification.
9 is an MS spectrum of Compound 2-9 according to an exemplary embodiment of the present specification.
10 is an MS spectrum of Compound 2-10 according to an exemplary embodiment of the present specification.
11 is an MS spectrum of Compound 2-11 according to an exemplary embodiment of the present specification.
12 is an MS spectrum of Compound 2-12 according to an exemplary embodiment of the present specification.
13 is an MS spectrum of Compound 2-13 according to an exemplary embodiment of the present specification.
14 is an MS spectrum of Compound 2-16 according to an exemplary embodiment of the present specification.
15 is a MS spectrum of compound 2-17 according to the exemplary embodiment of the present specification.
16 is an MS spectrum of Compound 2-20 according to an exemplary embodiment of the present specification.
17 is an MS spectrum of Compound 2-22 according to an exemplary embodiment of the present specification.

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

This specification 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, wherein the one or more organic material layers each include an organic light emitting device including a compound represented by Formula 1 or a compound represented by Formula 2, respectively. to provide.

When a member is referred to as being "on" another member in the present application, this includes not only the case where one member abuts 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 specifically stated otherwise.

Examples of substituents herein 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 can be substituted, 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" as used herein refers to deuterium; Halogen group; Cyano group; Nitro group; Carbonyl group; Ester groups; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide 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 consisting of substituted or unsubstituted 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 this specification, the number of carbon atoms of the ester group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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, styrenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; Cyano group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. Specifically, a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but are not limited thereto.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, but is 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 the amine group are methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine 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 N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.

In the present specification, the N-aryl heteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group can be selected from the examples of the aryl group described above.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 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, etc., 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 substituted or unsubstituted 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 non-carbon atoms and 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 of 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, but are not limited thereto. In the present specification, the heterocyclic group includes one or more non-carbon atoms and 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 of 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, but are not limited thereto.

In the present specification, the description of the aforementioned cycloalkyl group may be applied, except that the aliphatic hydrocarbon ring is a divalent group.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the aryl sulfoxy group, the arylphosphine group, and the arylamine group may be applied to the aryl group described above.

In the present specification, the alkyl group of the alkylthio group, the alkyl sulfoxy group, and the alkylamine group may be applied to the description of the aforementioned alkyl group.

In the present specification, a heteroaryl group among heteroaryl groups and heteroarylamine groups may be applied to the description of the aforementioned heterocyclic group.

In the present specification, the description of the aryl group described above may be applied, except that the arylene group and the aromatic hydrocarbon ring are divalent groups, respectively.

In the present specification, the description of the heterocyclic group described above may be applied, except that the heteroarylene group and the heterocycle are divalent groups.

In the present specification, the meaning of forming a substituted or unsubstituted ring by combining with adjacent groups to each other means an aliphatic hydrocarbon ring substituted or unsubstituted by combining with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; Or it means forming a substituted or unsubstituted aromatic heterocycle.

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, 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 be. 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.

In the present specification, the meaning that adjacent groups are bonded to each other to form a substituted or unsubstituted ring is, as described above, adjacent groups are bonded to each other to form a 5-8 membered hydrocarbon ring or a 5-8 membered heterocycle. It means to form, may be monocyclic or polycyclic, may be aliphatic, aromatic or a condensed form thereof, and is not limited thereto.

According to an exemplary embodiment of the present application, R1 to R3 are each independently hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted alkoxy group, It is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

Further, according to an exemplary embodiment of the present application, R1 to R3 are each independently 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, R1 to R3 are each independently, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; An aryl group unsubstituted or substituted with a group selected from the group consisting of deuterium, alkyl groups, and trialkylsilyl groups; Or a heterocyclic group.

Further, according to an exemplary embodiment of the present application, R1 to R3 are each independently, a methyl group; Ethyl group; Isopropyl group; tert-butyl group; A phenyl group unsubstituted or substituted with a group selected from the group consisting of deuterium, alkyl groups, and trialkylsilyl groups; Biphenyl group; Or a dibenzofuranyl group.

According to an exemplary embodiment of the present application, groups adjacent to each other among R1 to R3, A, B, and C may combine to form a substituted or unsubstituted ring.

In addition, according to an exemplary embodiment of the present application, groups adjacent to each other among R1 to R3, A, B, and C may combine to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heteroring.

In addition, according to an exemplary embodiment of the present application, groups adjacent to each other among R1 to R3, A, B, and C are bonded to a substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms. Can form.

In addition, according to an exemplary embodiment of the present application, a group adjacent to each other among R1 to R3, A, B, and C is a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms. Can form.

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 and C are the same as in claim 1,

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,

Groups adjacent to each other among R', R", A, B and C may combine to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heteroring.

According to the exemplary embodiment of the present application, the compound represented by Chemical Formula 1 may include at least one deuterium.

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

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

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

According to an exemplary embodiment of the present application, the formula 1 may be represented by the formula (3).

[Formula 3]

In Chemical Formula 3, X1 and X2 are as defined in Chemical Formula 1,

Z1 to Z3 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted amine 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, or adjacent groups may combine with each other to form a substituted or unsubstituted ring,

a and b are each an integer from 1 to 4,

c is an integer from 1 to 3,

When a to c are 2 or more, structures in parentheses are the same or different from each other.

According to an exemplary embodiment of the present application, Z1 to Z3 are each independently hydrogen, deuterium, a substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups may combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present application, Z1 to Z3 are each independently hydrogen; heavy hydrogen; Diarylamine unsubstituted or substituted with a group selected from the group consisting of deuterium, diarylamine and carbazole; Phenyl group; Biphenyl group; methyl; tert-butyl; Carbazole unsubstituted or substituted with a group selected from the group consisting of aryl groups and carbazole; Or a trialkylsilyl group, or adjacent groups may combine with each other to form a substituted or unsubstituted ring.

According to one embodiment of the present specification, when Z1 to Z3 and R1 to R3 each independently combine with an adjacent group to form a substituted or unsubstituted ring, adjacent groups directly bond to each other; Or it may be connected to any one of the following structures to form a ring.

In the above structure,

A1 to A24 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,

a1 to a11 are each an integer from 0 to 4,

a12 is an integer from 0 to 6,

* Indicates the position to be substituted.

According to an exemplary embodiment of the present application, the formula 1 may be represented by any one of the following formulas 3-1 to 3-3.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

In Chemical Formulas 3-1 to 3-3,

X3 is a direct bond, O, CR11R12 or NR13,

Z11 to Z19 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted amine 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, or adjacent groups may combine with each other to form a substituted or unsubstituted ring,

z11, z12 and z17 are each an integer from 1 to 4,

z13, z14, z15, z16, z18 and z19 are integers from 1 to 3,

When z11 to z19 are 2 or more, structures in parentheses are the same or different from each other,

R4 to R8 and R11 to R13 are each independently a 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, R4 to R8 are each independently, a substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present application, R4 to R8 are each independently a methyl group; Ethyl group; Isopropyl group; tert-butyl group; A phenyl group unsubstituted or substituted with a group selected from the group consisting of deuterium, alkyl groups, and trialkylsilyl groups; Biphenyl group; Or a dibenzofuranyl group.

According to an exemplary embodiment of the present application, R11 to R13 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present application, R11 to R13 are each independently hydrogen; heavy hydrogen; Methyl group; Or a phenyl group.

According to an exemplary embodiment of the present application, Z11 to Z19 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted amine 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, or adjacent groups may combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present application, Z11 to Z19 are each independently hydrogen; heavy hydrogen; Diarylamine unsubstituted or substituted with a group selected from the group consisting of deuterium, diarylamine and carbazole; Phenyl group; Biphenyl group; methyl; tert-butyl; Carbazole unsubstituted or substituted with a group selected from the group consisting of aryl groups and carbazole; Or a trialkylsilyl group, or adjacent groups may combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present application, when the adjacent groups of Z11 to Z19 combine with each other to form a substituted or unsubstituted ring, each independently substituted or unsubstituted indolo ring; A substituted or unsubstituted benzene ring; Or it may form a substituted or unsubstituted natalene ring.

According to an exemplary embodiment of the present application, when the adjacent groups of Z11 to Z19 combine with each other to form a substituted or unsubstituted ring, each independently substituted or unsubstituted aryl group indole ring; A benzene ring unsubstituted or substituted with an alkyl group; Or it can form a natalene ring.

According to an exemplary embodiment of the present application, when the adjacent groups of Z11 to Z19 combine with each other to form a substituted or unsubstituted ring, each independently substituted or unsubstituted phenyl group indolo ring; a benzene ring unsubstituted or substituted with a t-butyl group; Or it can form a natalene ring.

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

The organic light emitting device according to the exemplary embodiment of the present application includes a compound represented by the following Chemical Formula 2.

[Formula 2]

In Formula 2,

At least one of X4 to X6 is N and the other is CR',

Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L is a direct bond; A substituted or unsubstituted n+ monovalent aryl group; Or a substituted or unsubstituted n+1 monovalent heterocyclic group,

Y is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

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,

n is 1 or 2,

When n is 2, two Y's are the same or different from each other.

According to an exemplary embodiment of the present application, at least one of X4 to X6 is N and the other is CR'.

According to an exemplary embodiment of the present application, at least two of X4 to X6 is N and the other is CH.

According to one embodiment of the present application, two of X4 to X6 are N and the other is CH.

According to an exemplary embodiment of the present application, X4 to X6 is N.

According to an exemplary embodiment of the present application, Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present application, Ar1 and Ar2 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, Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present application, Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present application, Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present application, Ar1 and Ar2 are each independently, a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present application, Ar1 and Ar2 are each independently, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present application, Ar1 and Ar2 are each independently, a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; Or a substituted or unsubstituted pyrenyl group.

According to an exemplary embodiment of the present application, Ar1 and Ar2 are each independently, a phenyl group; Biphenyl group; Naphthyl group; Phenanthrenyl group; A fluorenyl group substituted with an alkyl group; Dibenzofuranyl group; Dibenzothiophenyl group; Or a pyrenyl group.

According to an exemplary embodiment of the present application, L is a direct bond; A substituted or unsubstituted n+ monovalent aryl group; Or a substituted or unsubstituted n + monovalent heterocyclic group.

According to an exemplary embodiment of the present application, L is a direct bond; A substituted or unsubstituted n+1 monovalent aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted n+1 monovalent heterocyclic group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present application, L is a direct bond; A substituted or unsubstituted n+1 monovalent aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted n+1 monovalent heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present application, L is a direct bond; A substituted or unsubstituted n+1 monovalent aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted n+1 monovalent heterocyclic group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present application, L is a substituted or unsubstituted trivalent aryl group; Or a substituted or unsubstituted trivalent heterocyclic group.

According to an exemplary embodiment of the present application, L is a substituted or unsubstituted trivalent aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted trivalent heterocyclic group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present application, L is a substituted or unsubstituted trivalent aryl group.

According to an exemplary embodiment of the present application, L is a substituted or unsubstituted trivalent aryl group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present application, L is a substituted or unsubstituted trivalent phenyl group; Or a substituted or unsubstituted trivalent biphenyl group.

According to an exemplary embodiment of the present application, L is a trivalent phenyl group; Or a trivalent biphenyl group.

According to an exemplary embodiment of the present application, Y is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present application, Y is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present application, Y is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present application, Y is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present application, Y is a substituted or unsubstituted polycyclic aryl group. Here, polycyclic means a state in which two or more rings are condensed.

According to an exemplary embodiment of the present application, Y is a substituted or unsubstituted 2 to 5 ring aryl group.

According to an exemplary embodiment of the present application, Y is a substituted or unsubstituted 2 to 4 ring aryl group.

According to an exemplary embodiment of the present application, Y is a substituted or unsubstituted 2 to 3 ring aryl group.

According to an exemplary embodiment of the present application, Y is a substituted or unsubstituted polycyclic aryl group having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present application, Y is a substituted or unsubstituted polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present application, Y is a substituted or unsubstituted polycyclic aryl group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present application, Y is a substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenenylenyl group; Or a substituted or unsubstituted fluorenyl group.

According to an exemplary embodiment of the present application, n is 1 or 2.

According to an exemplary embodiment of the present application, n is 2.

According to an exemplary embodiment of the present application, when n is 2, the two Y are the same.

According to an exemplary embodiment of the present application, when n is 2, the two Y are different from each other.

According to an exemplary embodiment of the present application, R'is hydrogen, deuterium, 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 It is an aryl group or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present application, R'is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present application, R'is hydrogen or deuterium.

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

For example, the compound of Formula 1 may have a core structure as shown in Scheme 1 below, and the compound of Formula 2 may have a core structure as shown in Scheme 2 below. Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be varied according to techniques known in the art.

[Scheme 1]

In Reaction Scheme 1, A, B and C are as defined in Chemical Formula 1,

D and E are each independently a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring,

A ₁ to A ₃ are functional groups capable of coupling reactions with amines, respectively.

Under the nitrogen atmosphere, an amine compound and a halogenated aromatic ring compound were obtained through a coupling reaction using a Pd catalyst to obtain a compound having the structure of formula (A).

Another amine compound of the same amount as in Formula A was added, and a compound having the structure of Formula B was obtained through a coupling reaction using a Pd catalyst. Further, a tert-butyl lithium (t-Butyl Lithium) solution was added to a flask containing a compound having the structure of Formula B at -80°C. After stirring for about 30 minutes, boron tribromide was added and the temperature was raised to room temperature. Thereafter, the mixture was cooled to 0°C again, N,N-diisopropylethylamine was added, the temperature was raised to 120°C, and the mixture was heated and stirred. After the reaction was completed, the mixture was cooled to room temperature, and a core structure of Formula 1-1-1 was obtained through a purification process.

[Scheme 2]

[Formula C]

[Formula D] [Formula 2]

In Reaction Scheme 2, X4 to X6, L, n, Ar1 and Ar2 are as defined in Chemical Formula 2.

In Reaction Scheme 2, a coupling reaction using a triazine compound and a boronic acid or boronate type linker as a catalyst for Pd was performed to obtain a compound having the structure of Formula C.

The same amount of bis(pinacolato)diboron (Bis) in dioxane solvent was added to the equivalent of formula C, and the base KOAc and Pd were used as catalysts to carry out a borylation reaction to perform formula D A compound having the structure of was obtained. In addition, a core structure of Formula 2 was obtained through a coupling reaction between a compound having the structure of Formula D and Y.

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 thereto, and may include a smaller number of organic material layers.

In an exemplary embodiment of the present application, the organic material layer may include a layer including the compound represented by Chemical Formula 2 between the first electrode and the light emitting layer.

In an exemplary embodiment of the present application, the organic material layer may include a layer including the compound represented by Chemical Formula 2 between the second electrode and the light emitting layer.

In one embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or a hole transport layer includes a compound represented by Chemical Formula 2.

In one embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Chemical Formula 1.

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

The light emitting layer may include a compound represented by Chemical Formula 1. Specifically, the light-emitting layer may include a host and a dopant including Formula 1.

The light emitting layer may include a compound represented by Chemical Formula 1 as a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran, and dibenzofuran Derivatives, dibenzothiophene, dibenzothiophene derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

In one embodiment of the present application, the weight ratio of the host and the dopant is 90: 10 to 99: 1. Specifically, it may be 90: 10, 91:9, 92:8, 93:7, 94:6, 95:5, 96:4, 97:3, 98:2, or 99:1, preferably 95:5, but is not limited thereto.

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

In one embodiment of the present application, the host includes an anthracene derivative. In this case, the anthracene derivative may be substituted or unsubstituted anthracene, and adjacent substituents among the substituents substituted on anthracene may combine with each other to form a substituted or unsubstituted ring.

In one embodiment of the present application, the host includes a compound represented by Formula 4 below.

[Formula 4]

In Chemical Formula 4,

L101 and L102 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R101 to R108 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or connected to an adjacent substituent to form a substituted or unsubstituted ring,

m1 and m2 are each an integer from 0 to 5,

When m1 is 2 or more, L101 is the same or different from each other,

When m2 is 2 or more, L102 is the same or different from each other.

In one embodiment of the present application, the host includes a compound represented by any one of the following structures.

.

.

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; A light emitting layer provided between the first electrode and the second electrode; And one or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode. In one embodiment of the present application, the organic material layer of one or more layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection, and a hole blocking layer.

In one embodiment of the present application, the organic light emitting device includes an anode; A cathode provided opposite the anode; An emission layer provided between the anode and the cathode and including a compound represented by the following Chemical Formula 1; A hole transport region provided between the anode and the emission layer; And an electron transport region provided between the cathode and the light emitting layer and including a compound represented by the following Chemical Formula 2.

In one embodiment of the present application, the hole transport region includes an organic material layer of one or more layers provided between the anode and the light emitting layer, and refers to a region that serves to transport holes from the anode to the light emitting layer. The hole transport region may include at least one layer of a hole injection layer, a hole transport layer, a hole injection and transport layer, a hole control layer, and an electron blocking layer.

In one embodiment of the present application, the electron transport region includes an organic material layer of one or more layers provided between the cathode and the light emitting layer, and means a region that receives holes from the cathode and transports holes to the light emitting layer. The electron transport region may include at least one of an electron injection layer, an electron transport layer, an electron injection and transport layer, an electron control layer, and a hole blocking layer.

The electron transport region includes an electron control layer, an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron control layer, The electron injection layer, the electron transport layer, or the electron injection and transport layer may include a compound represented by Formula 2 above.

In one embodiment of the present application, the electron transport region includes two or more electron transport layers, and at least one of the two or more electron transport layers includes a compound represented by Chemical Formula 2. Specifically, in one embodiment of the present application, the compound represented by Chemical Formula 2 may be included in one layer of the two or more electron transport layers, or may be included in each of the two or more electron transport layers.

In addition, in one embodiment of the present application, when the compound represented by Chemical Formula 2 is included in each of the two or more electron transport layers, other materials except the compound may be the same or different from each other.

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 hole transport region 10, a light emitting layer 3, an electron transport region 20, and a cathode 4 are sequentially stacked. . In this structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer 3, and the compound represented by Chemical Formula 2 may be included in the electron transport region 20.

2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron regulating layer 7, an electron injection and transport layer 8, and a cathode 4 The structure of this sequentially stacked organic light emitting device is illustrated. In this structure, the compound represented by Chemical Formula 1 is included in the light emitting layer 3, and the compound represented by Chemical Formula 2 can be included in the electron regulating layer 7 or the electron injection and transport layer 8.

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.

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.

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, that is, the compound represented by Formula 1.

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 an alloy 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 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing the 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 this method, an organic light emitting device may also be formed 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 (anode), and the second electrode is a cathode (cathode).

In another exemplary embodiment, the first electrode is a cathode (cathode), and the second electrode is an anode (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); ZnO:Al or SNO ₂ : Combination of metal and oxide such as Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into 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; There is a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection material is a layer for injecting holes from an electrode, and the hole injection material has the ability to transport holes, 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 a light emitting layer A compound that prevents migration of the excited excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. , Organic anthraquinone 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 the hole transport material, the hole is transported from the anode or the hole injection layer to the hole and is transported to the light emitting layer. 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.

The light emitting layer may further include an additional light emitting material in addition to the compound represented by Chemical Formula 1 described above. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; 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 transporting material is a layer that receives electrons from the cathode or the electron injection layer and transports electrons to the light emitting layer. As the electron transporting material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, the mobility of electrons Large materials are suitable. 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 those 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 the cathode, 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 injects holes 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, fluorenylidene 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-naphtolato) 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 compounds represented by Chemical Formulas 1 and 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 1: Formula 1]

<Production Example 1-1> Synthesis of Compound 1-1

One) Synthesis of Compound 1-1-A

[Compound 1-1-A]

Under nitrogen atmosphere, N-methylaniline (30.0 g), 1-bromo-2,3-dichlorobenzene (63 g), Pd(tBu3P) ₂ (0.29 g), NaOtBu (53.8) and xylene (500) ml) the flask containing the mixture was heated and stirred at 80°C for 4 hours, then heated to 120°C and further heated and stirred for 3 hours. After the reaction solution was cooled to room temperature, water and ethyl acetate were added and separated. Subsequently, it was purified by silica gel column chromatography (developer: toluene/heptane=1/20 (capacity ratio)) to obtain 2,3-dichloro-N-methyl-N-phenylaniline (64.0 g).

Here, tBu means tertbutyl.

MS [M+H] + =252

2) Synthesis of Compound 1-1-B

[Compound 1-1-A] [Compound 1-1-B]

Under nitrogen atmosphere, 2,3-dichloro-N-methyl-N-phenylaniline (20.0 g), N-methylaniline (8.5 g), Pd(t-Bu3P) ₂ (0.08 g), NaOtBu (15.2 g) and The flask containing xylene was heated and stirred at 120°C for 1 hour. After the reaction solution was cooled to room temperature, water and ethyl acetate were added and separated. Subsequently, it was purified by a silica gel short pass column (developing solution: heated toluene), and further washed with a mixed solvent of heptane and ethyl acetate (the volume ratio of heptane/ethyl acetate = 1) to obtain 2-chloro-N1,N3-. Dimethyl-N1,N3-diphenylbenzene-1,3-diamine (23.2 g) was obtained.

MS [M+H] + = 323

3) Synthesis of Compound 1-1

[Compound 1-1-B] [Compound 1-1]

In a flask containing 2-chloro-N1,N3-dimethyl-N1,N3-diphenylbenzene-1,3-diamine (25.0 g) and tert-butylbenzene (130 ml), at -30°C under nitrogen atmosphere, 1.6 M tert-butyllithium pentane solution (48.4 ml) was added. After the dropping was completed, the temperature was raised to 60° C. and stirred for 1 hour, and then a component having a lower boiling point than tert-butylbenzene was distilled off under reduced pressure. After cooling to -30°C, boron tribromide (10.6 ml) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then, it was cooled to 0°C again, N,N-diisopropylethylamine (12.8 ml) was added, and the mixture was stirred at room temperature until the exotherm had cooled, then heated to 120°C and stirred with heating for 2 hours. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled with an ice bath, followed by ethyl acetate, was added and separated. Then, it was purified by a silica gel short pass column (developing solution: heated chlorobenzene). After washing with refluxed heptane and refluxed ethyl acetate, the compound (16.3 g) represented by Chemical Formula 1-1 was obtained by reprecipitation from chlorobenzene.

MS [M+H] + = 297

<Production Example 1-2> Synthesis of Compound 1-2

One) Synthesis of Compound 1-2-A

[Compound 1-2-A]

Under a nitrogen atmosphere, diphenylamine (37.5 g), 1-bromo-2,3-dichlorobenzene (50.0 g), Pd(t-Bu3P) ₂ (0.58 g), NaOtBu (32.0 g) and xylene ) (500 ml) containing the flask was heated and stirred at 80° C. for 4 hours, then heated to 120° C. and further heated and stirred for 3 hours. After the reaction solution was cooled to room temperature, water and ethyl acetate were added and separated. Subsequently, it was purified by silica gel column chromatography (developing solution: toluene/heptane = 1/20 (capacity ratio)) to obtain 2,3-dichloro-N,N-diphenylaniline (63.0 g).

MS [M+H] + = 314

2) Synthesis of Compound 1-2-B

[Compound 1-2-A] [Compound 1-2-B]

Under nitrogen atmosphere, 2,3-dichloro-N,N-diphenylaniline (16.2g), di([1,1'-biphenyl]-4-yl)amine (15.0g), Pd(t-Bu3P) _The flask containing ₂ (0.22 g), NaOtBu (6.7 g) and xylene (150 ml) was heated and stirred at 120° C. for 1 hour. After the reaction solution was cooled to room temperature, water and ethyl acetate were added and separated. Subsequently, it was purified by a silica gel short pass column (developer: heated toluene), and further washed with a mixed solvent of heptane and ethyl acetate (heptane/ethyl acetate = 1, which is a ratio of these volumes) to N1,N1-di([1 ,1'-biphenyl]-4-yl)-2-chloro-N3,N3-diphenylbenzene-1,3-diamine (22.0 g).

MS [M+H] + = 599

3) Synthesis of Compound 1-2

[Compound 1-2-B] [Compound 1-2]

N1,N1-di([1,1'-biphenyl]-4-yl)-2-chloro-N3,N3-diphenylbenzene-1,3-diamine (22.0 g) and tert-butylbenzene (130 ml To a flask containing ), 1.6 M tert-butyllithium pentane solution (48.4 ml) was added at -30 DEG C under nitrogen atmosphere. After the dropping was completed, the temperature was raised to 60° C. and stirred for 1 hour, and then a component having a lower boiling point than tert-butylbenzene was distilled off under reduced pressure. After cooling to -30°C, boron tribromide (6.2 ml) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then, it was cooled to 0°C again, N,N-diisopropylethylamine (12.8 ml) was added, and the mixture was stirred at room temperature until the exotherm had cooled, then heated to 120°C and stirred with heating for 2 hours. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled with an ice bath, followed by ethyl acetate, was added and separated. Then, it was purified by a silica gel short pass column (developing solution: heated chlorobenzene). After washing with refluxed heptane and refluxed ethyl acetate, the compound (11.2 g) represented by Chemical Formula 1-2 was obtained by reprecipitation from chlorobenzene.

MS [M+H] + = 573

<Production Example 3> Synthesis of Compound 1-3

One) Synthesis of Compound 1-3-A

[Compound 1-3-A]

Compound 1-3-A was prepared by the same method as Compound 1-1-A, except that di([1,1'-biphenyl]-3-yl)amine was used instead of N-methylaniline.

MS [M+H] + = 466

2) Synthesis of Compound 1-3-B

[Compound 1-3-A] [Compound 1-3-B]

Compound 1-, except that [Compound 1-3-A] was used instead of [Compound 1-1-A] and N1,N1,N3-triphenylbenzene-1,3-diamine was used instead of N-methylaniline. Compound 1-3-B was prepared by the same method as 1-B.

MS [M+H] + = 614

3) Synthesis of Compound 1-3

[Compound 1-3-B] [Compound 1-3]

Compound 1-3 was prepared by the same method as Compound 1-1, except that [Compound 1-3-B] was used instead of [Compound 1-1-B].

MS [M+H] + = 740

<Production Example 1-4> Synthesis of Compound 1-4

One) Synthesis of Compound 1-4-A

[Compound 1-4-A]

1-bromo-2,3-dichloro-5-methylbenzene is used instead of 1-bromo-2,3-dichlorobenzene, and 3,5-di-tert-butyl-N-(3 is substituted for N-methylaniline. Compound 1-4-A was prepared by the same method as Compound 1-1-A, except that -(tert-butyl)phenyl)aniline was used.

MS [M+H] + = 496

2) Synthesis of Compound 1-4-B

Compound 1-1-B except that [Compound 1-4-A] was used instead of [Compound 1-1-A] and bis(4-(tert-butyl)phenyl)amine was used instead of N-methylaniline. Compound 1-4-B was prepared by the same method.

MS [M+H] + = 741

3) Synthesis of Compound 1-4

[Compound 1-4-B] [Compound 1-4]

Compound 1-4 was prepared by the same method as Compound 1-1, except that [Compound 1-4-B] was used instead of [Compound 1-1-B].

MS [M+H] + =715

<Production Example 1-5> Synthesis of Compound 1-5

One) Synthesis of Compound 1-5-A

[Compound 1-5-A]

Compound 1-5-A was prepared by the same method as Compound 1-1-A, except that N,9-diphenyl-9H-carbazole-2-amine was used instead of N-methylaniline.

MS [M+H] + = 479

2) Synthesis of Compound 1-5-B

[Compound 1-5-A] [Compound 1-5-B]

Compound 1-, except that [Compound 1-5-A] was used instead of [Compound 1-1-A] and N1,N1,N3-triphenylbenzene-1,3-diamine was used instead of N-methylaniline. Compound 1-5-B was prepared by the same method as 1-B.

MS [M+H] + = 779

3) Synthesis of Compound 1-5

[Compound 1-5-B] [Compound 1-5]

Compound 1-5 was prepared by the same method as Compound 1-1, except that [Compound 1-5-B] was used instead of [Compound 1-1-B].

MS [M+H] + =753

<Production Example 1-6> Synthesis of Compound 1-6

One) Synthesis of Compound 1-6-A

[Compound 1-6-A]

Compound 1-6-A was prepared by the same method as Compound 1-1-A, except that N-phenylnaphthalen-2-amine was used instead of N-methylaniline.

MS [M+H] + = 364

2) Synthesis of Compound 1-6-B

[Compound 1-6-A] [Compound 1-6-B]

Compound 1-6- in the same manner as Compound 1-1-B, except that [Compound 1-6-A] was used instead of [Compound 1-1-A] and diphenylamine was used instead of N-methylaniline. B was prepared.

MS [M+H] + = 497

3) Synthesis of Compound 1-6

[Compound 1-6-B] [Compound 1-6]

Compound 1-6 was manufactured by the same method as Compound 1-1, except that [Compound 1-6-B] was used instead of [Compound 1-1-B].

MS [M+H] + =471

<Production Example 1-7> Synthesis of Compound 1-7

One) Synthesis of Compound 1-7-A

9-(3-bromo-4,5-dichlorophenyl)-9H-carbazole was used instead of 1-bromo-2,3-dichlorobenzene, and 3-(tert-butyl)-N instead of N-methylaniline Compound 1-7-A was prepared by the same method as Compound 1-1-A, except that -(4-(tert-butyl)phenyl)aniline was used.

MS [M+H] + = 591

2) Synthesis of Compound 1-7-B

Compound 1-1-B, except that [Compound 1-7-A] was used instead of [Compound 1-1-A] and bis(4-(tert-butyl)phenyl)amine was used instead of N-methylaniline. Compound 1-7-B was prepared by the same method.

MS [M+H] + =836

3) Synthesis of Compound 1-7

Compound 1-7 was manufactured by the same method as Compound 1-1, except that [Compound 1-7-B] was used instead of [Compound 1-1-B].

MS [M+H]+ = 810

<Production Example 1-8> Synthesis of Compound 1-8

One) Synthesis of Compound 1-8-A

[Compound 1-8-A]

3-Bromo-4,5-dichloro-N,N-diphenylaniline is used instead of 1-bromo-2,3-dichlorobenzene, and 3-(tert-butyl)-N-( instead of N-methylaniline Compound 1-8-A was prepared by the same method as Compound 1-1-A, except that 4-(tert-butyl)phenyl)aniline was used.

MS [M+H] + = 593

2) Synthesis of Compound 1-8-B

[Compound 1-8-A] was used instead of [Compound 1-1-A], and 3-(tert-butyl)-N-(4-(tert-butyl)phenyl)aniline was used instead of N-methylaniline. Compound 1-8-B was prepared by the same method as Compound 1-1-B.

MS [M+H] + = 838

3) Synthesis of Compound 1-8

Compound 1-8 was prepared by the same method as Compound 1-1, except that [Compound 1-8-B] was used instead of [Compound 1-1-B].

MS [M+H] + = 812

<Production Example 1-9> Synthesis of Compound 1-9

One) Synthesis of Compound 1-9-A

[Compound 1-9-A]

Compound 1-9-A was prepared by the same method as Compound 1-1-A, except that N-phenyldibenzo[b,d]furan-3-amine was used instead of N-methylaniline.

MS [M+H] + = 404

2) Synthesis of Compound 1-9-B

Compound 1-, except that [Compound 1-9-A] was used instead of [Compound 1-1-A] and N-phenyldibenzo[b,d]furan-3-amine was used instead of N-methylaniline. Compound 1-9-B was prepared by the same method as 1-B.

MS [M+H] + = 627

3) Synthesis of Compound 1-9

Compound 1-9 was prepared by the same method as Compound 1-1, except that [Compound 1-9-B] was used instead of [Compound 1-1-B].

MS [M+H] + = 601

<Production Example 1-10> Synthesis of Compound 1-10

One) Synthesis of Compound 1-10-A

[Compound 1-10-A]

Use N-phenyl-4-(trimethylsilyl)aniline instead of N-methylaniline and 3-bromo-4,5-dichloro-N,N-diphenylaniline instead of 1-bromo-2,3-dichlorobenzene. Compound 1-10-A was prepared according to the same method as Compound 1-1-A except for the use.

MS [M+H] + = 553

2) Synthesis of Compound 1-10-B

[Compound 1-10-A] [Compound 1-10-B]

Compound 1-1-B, except that [Compound 1-10-A] is used instead of [Compound 1-1-A] and N-phenyl-4-(trimethylsilyl)aniline is used instead of N-methylaniline. Compound 1-10-B was prepared by the same method.

MS [M+H] + =758

3) Synthesis of Compound 1-10

[Compound 1-10-B] [Compound 1-10]

Compound 1-10 was prepared by the same method as Compound 1-1, except that [Compound 1-10-B] was used instead of [Compound 1-1-B].

MS [M+H] + =732

<Production Example 1-11> Synthesis of Compound 1-11

One) Synthesis of Compound 1-11-A

[Compound 1-11-A]

4-(tert-butyl)-N-phenylaniline is used instead of N-methylaniline and 3-bromo-4,5-dichloro-N,N-diphenylaniline is substituted for 1-bromo-2,3-dichlorobenzene Compound 1-11-A was prepared by the same method as Compound 1-1-A, except that was used.

MS [M+H] + = 557

2) Synthesis of Compound 1-11-B

[Compound 1-11-A] was used instead of [Compound 1-1-A], and N-(4-(tert-butyl)phenyl)-3-fluoroaniline was used instead of N-methylaniline. Compound 1-11-B was prepared by the same method as compound 1-1-B.

MS [M+H] + =744

3) Synthesis of Compound 1-11-C

Compound 1-11-C was prepared by the same method as Compound 1-1, except that [Compound 1-11-B] was used instead of [Compound 1-1-B].

MS [M+H]+ = 718

4) Synthesis of Compound 1-11

Under nitrogen atmosphere, [Compound 1-11-C] (20 g), potassium carbonate (potassium carbonate) (7.7 g) and Pd (PPh ₃ ) ₄ (Tetrakis(triphenylphosphine)palladium(0)) (1.61 g) were dimethylacetate Put in amide (dimethylacetamide) (140 ml) and heated and stirred at 120° C. for 1 hour. The reaction solution was cooled to room temperature, and then filtered. Then, purified by a silica gel short pass column (developer: heated toluene), and further washed with a mixed solvent of heptane and ethyl acetate (the volume ratio of heptane/ethyl acetate = 1), [Compound 1-11] (28.0 g).

MS [M+H] + = 698

[Production Example 2: Formula 2]

<Production Example 2-1> Synthesis of Compound 2-1

One) Synthesis of Compound 2-1-A

[Compound 2-1-A]

2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (15g, 43.6mmol) and (3,5-dichloro) under nitrogen stream After dissolving phenyl)boronic acid (9.2g, 47.9mmol) in 150 mL of Tedrahydrofuran solvent, aqueous potassium carbonate (12.1g, 87.3mmol) solution was added and stirred with heating. Pd(PPh ₃ ) ₄ (1.5g, 1.3mmol) was added under reflux, followed by heating and stirring for 6 hours. After the reaction was completed, the temperature was lowered to room temperature, and the potassium carbonate solution was removed and filtered. The filtered solid was washed with ethanol to prepare compound 2-1-A (17.8 g, yield 90%).

MS [M+H] + = 454

2) Synthesis of Compound 2-1-B

[Compound 2-1-A] [Compound 2-1-B]

Compound 2-1-A (17.8 g, 39.2 mmol), bis (pinacolato) diborone (10.9 g, 43.1 mmol) was dissolved in 180 mL of dioxane solvent under a nitrogen stream, and then potassium acetate (11.5 g, 117.5 mmol) And stirred for heating. In reflux, Pd(dba) ₂ (Bis(dibenzylideneacetone)palladium(0)) (0.7g. 1.2mmol) and PCy ₃ (Tricyclohexylphosphine) (0.7g, 2.4mmol) were added and heated and stirred for 8 hours. After the reaction was completed, the temperature was lowered to room temperature, and then filtered first to remove impurities. The filtrate was poured into water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the mixture was washed with ethanol to prepare compound 2-1-B (21 g, yield 84%).

MS [M+H] + = 638

3) Synthesis of Compound 2-1

[Compound 2-1-B] [Compound 2-1]

Compound 2-1-B (21g, 32.9mmol) and 1-bromonaphthalene (14.3g, 69.2mmol) were dissolved in tetrahydrofuran under a stream of nitrogen, put into an aqueous solution of potassium carbonate (18.2g, 132.8mmol), and heated and stirred. Did. In the reflux state, the catalyst Pd(PPh ₃ ) ₄ (1.2g, 1.0mmol) was added, and the mixture was heated and stirred for 8 hours. After the reaction was completed, the temperature was lowered to room temperature, and the potassium carbonate solution was removed and filtered. The filtered solid was washed with ethanol to prepare compound 2-1 (18 g, yield 85%).

MS [M+H] + = 638

Synthetic confirmation data of the compound 2-1 is shown in Figure 3.

<Production Example 2-2> Synthesis of Compound 2-2

[Compound 2-1-B] [Compound 2-2]

Compound 2-1-B (21g, 32.9mmol) and 2-bromonaphthalene (14.3g, 69.2mmol) were dissolved in tetrahydrofuran under a stream of nitrogen, put into an aqueous solution of potassium carbonate (18.2g, 132.8mmol), and heated and stirred. Did. In the reflux state, the catalyst Pd(PPh ₃ ) ₄ (1.2g, 1.0mmol) was added, and the mixture was heated and stirred for 8 hours. After the reaction was completed, the temperature was lowered to room temperature, and the potassium carbonate solution was removed and filtered. The filtered solid was washed with ethanol to prepare compound 2-2 (18 g, yield 85%).

MS [M+H] + = 638

Synthetic confirmation data of the compound 2-2 is shown in Figure 4.

<Production Example 2-3> Synthesis of Compound 2-3

1) Synthesis of Compound 2-3-A

Compound 2-3-A was prepared by the same method as Compound 2-1-A, except that (3-bromo-5-chlorophenyl)boronic acid was used instead of (3,5-dichlorophenyl)boronic acid.

MS [M+H] + = 499

2) Synthesis of Compound 2-3-B

Compound 2-3-A (20g, 40.1mmol) and 1-naphthalenylboronic acid (7.6g, 44.1mmol) were dissolved in 1.4-dioxane under a nitrogen stream, and then put in an aqueous solution of potassium phosphate (17.0g, 80.2mmol). It was stirred with heating. In the reflux state, the catalyst Pd(PPh ₃ ) ₄ (1.4g, 1.2mmol) was added and stirred with heating for 8 hours. After the reaction was completed, the temperature was lowered to room temperature, and the potassium phosphate solution was removed and filtered. The filtered solid was washed with ethanol to prepare compound 2-3-B (18 g, yield 82%).

MS [M+H] + = 546

3) Synthesis of Compound 2-3

[Compound 2-3-B] [Compound 2-3]

In the same manner as in Compound 2-1, except that Compound 2-3-B was used instead of Compound 2-1-B and (4-(1-naphthalenyl)phenyl)boronic acid was used instead of 1-bromonaphthalene. Compound 2-3 was prepared.

MS [M+H] + =714

Synthetic confirmation data of the compound 2-3 is shown in Figure 5.

<Production Example 2-4> Synthesis of Compound 2-4

[Compound 2-3-B] [Compound 2-4]

Compound 2-4 was prepared by the same method as Compound 2-3, except that (4-(2-naphthalenyl)phenyl)boronic acid was used instead of (4-(1-naphthalenyl)phenyl)boronic acid. .

MS [M+H] + =714

Synthetic confirmation data of the compound 2-4 is shown in Figure 6.

<Production Example 2-5> Synthesis of Compound 2-5

1) Synthesis of Compound 2-5-B

[Compound 2-5-B] [Compound 2-5]

Compound 2-5-B was prepared by the same method as Compound 2-3-B, except that 2-naphthalenylboronic acid was used instead of 1-naphthalenylboronic acid.

MS [M+H] + = 546

2) Synthesis of Compound 2-5

Except that Compound 2-5-B was used instead of Compound 2-3-B and (4-(2-naphthalenyl)phenyl)boronic acid was used instead of (4-(1-naphthalenyl)phenyl)boronic acid. , Compound 2-5 was prepared by the same method as Compound 2-3.

MS [M+H] + =714

Synthetic confirmation data of the compound 2-5 is shown in Figure 7.

<Production Example 2-6> Synthesis of Compound 2-6

[Compound 2-6]

Compound 2-6 was prepared by the same method as Compound 2-5, except that (4-(1-naphthalenyl)phenyl)boronic acid was used instead of (4-(2-naphthalenyl)phenyl)boronic acid. .

MS [M+H] + =714

The synthesis confirmation data of the compound 2-6 is shown in FIG. 8.

<Production Example 2-7> Synthesis of Compound 2-7

Compound 2-7 was prepared by the same method as Compound 2-1, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

MS [M+H] + =738

<Production Example 2-8> Synthesis of Compound 2-8

1) Synthesis of Compound 2-8-A

2-([1,1'-biphenyl]-4-yl)-4-(-6)-phenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-3- 1)-4-Chloro-6-phenyl-1,3,5-triazine Compound 2-8-A was prepared by the same method as Compound 2-1-A, except that it was used.

MS [M+H] + = 454

2) Synthesis of Compound 2-8-B

Compound 2-8-B was prepared by the same method as Compound 2-1-B, except that Compound 2-8-A was used instead of Compound 2-1-A.

MS [M+H] + = 638

3) Synthesis of Compound 2-8

Compound 2-8 was prepared by the same method as Compound 2-7, except that Compound 2-8-B was used instead of Compound 2-1-B.

MS [M+H] + =738

<Production Example 2-9> Synthesis of Compound 2-9

Compound 2-9 was prepared by the same method as Compound 2-8, except that 1-bromonaphthalene was used instead of 9-bromophenanthrene.

MS [M+H] + = 638

Synthetic confirmation data of the compound 2-9 is shown in Figure 9.

<Production Example 2-10> Synthesis of Compound 2-10

Compound 2-10 was prepared by the same method as Compound 2-8, except that 2-bromonaphthalene was used instead of 9-bromophenanthrene.

MS [M+H] + = 638

Synthetic confirmation data of the compound 2-10 is shown in Figure 10.

<Production Example 2-11> Synthesis of Compound 2-11

1) Synthesis of Compound 2-11-A

2-([1,1'-biphenyl]-4-yl)-4-(-6)-phenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-3- 1)-4-Chloro-6-phenyl-1,3,5-triazine Compound 2-11-A was prepared by the same method as Compound 2-3-A, except that it was used.

MS [M+H] + = 499

2) Synthesis of Compound 2-11-B

Compound 2-11-B was prepared by the same method as Compound 2-3-B, except that 2-11-A was used instead of Compound 2-3-A.

MS [M+H] + = 546

3) Synthesis of Compound 2-11

Compound 2-11 was prepared by the same method as Compound 2-3, except that Compound 2-11-B was used instead of Compound 2-3-B.

MS [M+H] + =714

Synthesis confirmation data of Compound 2-11 is shown in FIG. 11.

<Production Example 2-12> Synthesis of Compound 2-12

Compound 2-12 was prepared by the same method as Compound 2-4, except that Compound 2-11-B was used instead of Compound 2-3-B.

MS [M+H] + =714

Synthetic confirmation data of the compound 2-12 is shown in Figure 12.

<Production Example 2-13> Synthesis of Compound 2-13

1) Synthesis of Compound 2-13-B

Compound 2-13-B was prepared by the same method as Compound 2-5-B, except that Compound 2-11-A was used instead of Compound 2-3-A.

MS [M+H] + = 546

2) Synthesis of Compound 2-13

Compound 2-13 was prepared by the same method as Compound 2-5, except that Compound 2-13-B was used instead of Compound 2-5-B.

MS [M+H] + =714

Synthesis confirmation data of Compound 2-13 is shown in FIG. 13.

<Production Example 2-14> Synthesis of Compound 2-14

Compound 2-14 was prepared by the same method as Compound 2-13, except that (4-(naphthalen-1-yl)phenyl)boronic acid was used instead of (4-(naphthalen-2-yl)phenyl)boronic acid. .

MS [M+H] + =714

<Production Example 2-16> Synthesis of Compound 2-16

1) Synthesis of Compound 2-16-A

2-Chloro-4-(dibenzo[b,d]furan instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine Compound 1-16-A was prepared in the same manner as compound 2-1-A, except that -1-yl)-6-phenyl-1,3,5-triazine was used.

MS [M+H] + = 468

2) Synthesis of Compound 2-16-B

Compound 2-16-B was prepared by the same method as Compound 2-1-B, except that Compound 2-16-A was used instead of Compound 2-1-A.

MS [M+H] + = 652

3) Synthesis of Compound 2-16

Compound 2-16 was prepared by the same method as Compound 2-1, except that Compound 2-16-B was used instead of Compound 2-1-B.

MS [M+H] + = 652

Synthetic confirmation data of the compound 2-16 is shown in Figure 14.

<Production Example 2-17> Synthesis of Compound 2-17

Compound 2-17 was prepared by the same method as Compound 2-1, except that Compound 2-16-B was used instead of Compound 2-1-B and 2-bromonaphthalene was used instead of 1-bromonaphthalene.

MS [M+H] + = 652

Synthetic confirmation data of the compound 2-17 is shown in Figure 15.

<Production Example 2-18> Synthesis of Compound 2-18

1) Synthesis of Compound 2-18-A

2-Chloro-4-(dibenzo[b,d]furan instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine Compound 1-18-A was prepared by the same method as compound 2-3-A, except that -1-yl)-6-phenyl-1,3,5-triazine was used.

MS [M+H]+ = 512

2) Synthesis of Compound 2-18-B

Compound 2-18-B was prepared by the same method as Compound 2-3-B, except that Compound 2-18-A was used instead of Compound 2-3-A.

MS [M+H] + = 560

3) Synthesis of Compound 2-18

Compound 2-18 was prepared by the same method as Compound 2-3, except that Compound 2-18-B was used instead of Compound 2-3-B.

MS [M+H] + = 728

<Production Example 2-19> Synthesis of Compound 2-19

Compound 2-19 was prepared by the same method as Compound 2-4, except that Compound 2-18-B was used instead of Compound 2-3-B.

MS [M+H] + = 728

<Production Example 2-20> Synthesis of Compound 2-20

1) Synthesis of Compound 2-20-B

Compound 2-20-B was prepared by the same method as Compound 2-18-B, except that 2-naphthalene boronic acid was used instead of 1-naphthalene boronic acid.

MS [M+H] + = 560

2) Synthesis of Compound 2-20

Compound 2-20 was prepared by the same method as Compound 2-5, except that Compound 2-20-B was used instead of Compound 2-5-B.

MS [M+H] + = 728

Synthetic confirmation data of the compound 2-20 is shown in Figure 16.

<Production Example 2-21> Synthesis of Compound 2-21

Compound 2-21 was prepared by the same method as Compound 2-20, except that (4-(naphthalen-1-yl)phenyl)boronic acid was used instead of (4-(naphthalen-2-yl)phenyl)boronic acid. .

MS [M+H] + = 728

<Production Example 2-22> Synthesis of Compound 2-22

Compound 2-22 was prepared by the same method as Compound 2-16, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

MS [M+H] + =752

Synthetic confirmation data of the compound 2-22 is shown in Figure 17.

<Production Example 2-23> Synthesis of Compound 2-23

1) Synthesis of Compound 2-23-A

Compound 2-23-A was prepared by the same method as Compound 2-1-A, except that (2,5-dichlorophenyl)boronic acid was used instead of (3,5-dichlorophenyl)boronic acid.

MS [M+H] + = 454

2) Synthesis of Compound 2-23-B

Compound 2-23-B was prepared by the same method as Compound 2-1-B, except that Compound 2-23-A was used instead of Compound 2-1-A.

MS [M+H] + = 638

3) Synthesis of Compound 2-23

Compound 2-23 was prepared by the same method as Compound 2-1, except that Compound 2-23-B was used instead of Compound 2-1-B.

MS [M+H] + = 638

<Production Example 2-24> Synthesis of Compound 2-24

Compound 2-24 was prepared according to the same method as Compound 2-23, except that 2-bromonaphthalene was used instead of 1-bromonaphthalene.

MS [M+H] + = 638

<Production Example 2-25> Synthesis of Compound 2-25

Compound 2-25 was prepared by the same method as Compound 2-23, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

MS [M+H] + =738

<Production Example 2-26> Synthesis of Compound 2-26

1) Synthesis of Compound 2-26-A

2-Chloro-4-(naphthalen-2-yl)-6 instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine Compound 2-, except that (2-bromo-4-chlorophenyl)boronic acid was used instead of (3-bromo-5-chlorophenyl)boronic acid using -phenyl-1,3,5-triazine Compound 2-26-A was prepared by the same method as 3-A.

MS [M+H] + = 472

2) Synthesis of Compound 2-26-B

Compound 2-26-B was prepared by the same method as Compound 2-3-B, except that Compound 2-26-A was used instead of Compound 2-3-A.

MS [M+H] + = 520

3) Synthesis of Compound 2-26

Except that Compound 2-26-B was used instead of Compound 2-3-B and (4-(phenanthrene-9-yl)phenyl)boronic acid was used instead of (4-(naphthalen-1-yl)phenyl)boronic acid. Then, compound 2-26 was prepared by the same method as compound 2-3.

MS [M+H] + =738

[Example]

<Example 1-1>

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) at a thickness of 100 nm was placed in distilled water in which a dispersant was dissolved and washed with ultrasonic waves. The detergent used was a product of Fischer Co., and distilled water was used for Millipore Co. As the product filter, distilled water filtered secondarily was used. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated for 2 minutes with distilled water twice. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the prepared ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT-CN) was thermally vacuum-deposited to form a 50 nm thick hole injection layer.

A hole transport layer having a thickness of 40 nm was formed by vacuum-depositing compound HT1, a material for transporting holes thereon.

H1 and Compound 1-1 were vacuum deposited on the hole transport layer at a weight ratio of 25:1 to form a 30 nm thick light emitting layer.

Compound ET1 was vacuum-deposited on the light emitting layer to form an electron control layer having a thickness of 3 nm.

Compound 2-1 and compound LiQ (Lithium Quinolate) were vacuum-deposited on a weight ratio of 1:1 on the electron control layer to form an electron injection and transport layer having a thickness of 35 nm.

Lithium fluoride (LiF) and aluminum were sequentially deposited on the electron injection and transport layer to a thickness of 1.2 nm and 200 nm to form a cathode to prepare an organic light emitting device.

In the above process, the deposition rate of the organic material was maintained at 0.04 nm/sec to 0.07 nm/sec, the deposition rate of lithium fluoride was maintained at 0.03 nm/sec, and the deposition rate of aluminum was maintained at 0.2 nm/sec, The vacuum degree during deposition is 2 × 10 ^-7 torr to 5×10 ⁻⁶ torr was maintained.

<Examples 1-2 to 1-17>

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Table 1 below instead of the compound 1-1 and the compound 2-1, respectively.

<Comparative Examples 1-1 to 1-17>

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Table 1 below instead of the compound 1-1 and the compound 2-1, respectively.

For each of the organic light emitting diodes of Examples and Comparative Examples, driving voltage and luminous efficiency were measured at a current density of 10 mA/cm ² , and the time at which the luminance became 98% compared to the initial luminance at a current density of 20 mA/cm ² (LT98). Was measured. The results are shown in Table 1 below.

Emitting layer Electron injection and transport layer Voltage
(V) Current efficiency
(cd/A) Color coordinate
(x,y) LT98(h) Example 1-1 Compound 1-1 Compound 2-1 3.78 4.59 (0.142, 0.126) 190 Example 1-2 Compound 1-2 Compound 2-6 3.71 4.67 (0.142, 0.126) 196 Example 1-3 Compound 1-3 Compound 2-8 3.83 4.55 (0.142, 0.127) 180 Example 1-4 Compound 1-4 Compound 2-11 3.82 4.58 (0.142, 0.126) 177 Example 1-5 Compound 1-8 Compound 2-2 3.76 4.45 (0.142, 0.126) 183 Example 1-6 Compound 1-9 Compound 2-3 3.82 4.61 (0.142, 0.126) 213 Example 1-7 Compound 1-5 Compound 2-4 3.81 4.56 (0.142, 0.127) 200 Example 1-8 Compound 1-10 Compound 2-5 3.80 4.53 (0.142, 0.126) 191 Example 1-9 Compound 1-6 Compound 2-7 3.85 4.59 (0.142, 0.127) 195 Example 1-10 Compound 1-7 Compound 2-9 3.76 4.62 (0.142, 0.126) 184 Example 1-11 Compound 1-11 Compound 2-2 3.80 4.52 (0.142, 0.127) 177 Example 1-12 Compound 1-4 Compound 2-5 3.80 4.60 (0.142, 0.127) 195 Example 1-13 Compound 1-8 Compound 2-10 3.75 4.57 (0.142, 0.126) 180 Example 1-14 Compound 1-3 Compound 2-13 3.79 4.60 (0.142, 0.126) 178 Example 1-15 Compound 1-10 Compound 2-18 3.80 4.59 (0.142, 0.126) 183 Example 1-16 Compound 1-11 Compound 2-23 3.77 4.55 (0.142, 0.126) 179 Examples 1-17 Compound 1-4 Compound 2-26 3.84 4.58 (0.142, 0.126) 185 Comparative Example 1-1 D-A Compound 2-1 4.10 4.01 (0.142, 0.127) 100 Comparative Example 1-2 D-B Compound 2-3 4.13 4.11 (0.142, 0.126) 112 Comparative Example 1-3 D-C Compound 2-7 4.11 4.00 (0.142, 0.127) 104 Comparative Example 1-4 D-D Compound 2-11 4.09 4.05 (0.142, 0.127) 115 Comparative Example 1-5 D-E Compound 2-18 4.04 3.92 (0.142, 0.127) 96 Comparative Example 1-6 D-F Compound 2-8 4.08 3.99 (0.142, 0.128) 102 Comparative Example 1-7 Compound 1-4 ET-A 4.07 4.15 (0.142, 0.127) 91 Comparative Example 1-8 Compound 1-10 ET-B 4.05 4.20 (0.142, 0.126) 87 Comparative Example 1-9 Compound 1-1 ET-C 4.12 4.07 (0.142, 0.127) 95 Comparative Example 1-10 Compound 1-9 ET-D 4.09 4.19 (0.142, 0.126) 92 Comparative Example 1-11 Compound 1-3 ET-E 4.15 4.03 (0.142, 0.127) 86 Comparative Example 1-12 Compound 1-11 ET-F 4.14 4.13 (0.142, 0.126) 90 Comparative Example 1-13 D-A ET-B 4.03 3.87 (0.142, 0.126) 86 Comparative Example 1-14 D-F ET-D 4.08 3.95 (0.142, 0.127) 88 Comparative Example 1-15 Compound 1-6 ET-G 4.06 4.10 (0.142, 0.127) 101 Comparative Example 1-16 Compound 1-9 ET-H 4.09 4.12 (0.142, 0.127) 106 Comparative Example 1-17 D-D ET-I 4.11 3.92 (0.142, 0.127) 91

1: Substrate
2: anode
3: light emitting layer
4: Cathode
5: hole injection layer
6: hole transport layer
7: Electronic control layer
8: electron injection and transport layer
10: hole transport area
20: electron transport area

Claims (8)

Anode; A cathode provided opposite the anode;
An emission layer provided between the anode and the cathode and including a compound represented by the following Chemical Formula 1;
A hole transport region provided between the anode and the emission layer; And
An organic light-emitting device provided between the cathode and the light-emitting layer and including an electron transport region including a compound represented by Formula 2 below:
[Formula 1]

In Formula 1,
A, B and C are each independently a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring,
X1 and X2 are each independently O, CR1R2 or NR3,
R1 to R3 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,
R1 to R3, A, B and C adjacent groups may combine with each other to form a substituted or unsubstituted ring,
[Formula 2]

In Formula 2,
At least two of X4 to X6 are N and the rest are CH,
Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L is a substituted or unsubstituted trivalent aryl group; Or a substituted or unsubstituted trivalent heterocyclic group,
Y is a substituted or unsubstituted polycyclic aryl group,
n is 2,
When n is 2, two Y's are the same or different from each other. 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 and C are the same as in claim 1,
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,
Groups adjacent to each other among R', R", A, B and C may combine to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heteroring. The method according to claim 1,
Formula 1 is an organic light emitting device is selected from the following structural formula:

. The method according to claim 1,
Formula 2 is a compound selected from the following structural formula:

. The method according to claim 1, The light emitting layer is an organic light emitting device comprising a host and a dopant comprising the formula (1). The method according to claim 5, The weight ratio of the host and the dopant is 90: 10 to 99: 1 organic light emitting device. The method according to claim 5, The host is an organic light-emitting device comprising a compound represented by the formula (4):
[Formula 4]

In Chemical Formula 4,
L101 and L102 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R101 to R108 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,
Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or connected to an adjacent substituent to form a substituted or unsubstituted ring,
m1 and m2 are each an integer from 0 to 5,
When m1 is 2 or more, L101 is the same or different from each other,
When m2 is 2 or more, L102 is the same or different from each other. The method according to claim 1, The electron transport region includes an electron control layer, an electron injection layer, an electron transport layer, or an electron injection and transport layer, the electron control layer, The electron injection layer, the electron transport layer, or the electron injection and transport layer is an organic light emitting device comprising a compound represented by the formula (2).

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