KR102181840B1 - Multicyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

Description

A polycyclic compound and an organic light-emitting device including the same TECHNICAL FIELD

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2018-0003778 filed with the Korean Intellectual Property Office on January 11, 2018, the entire contents of which are incorporated herein.

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

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.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. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground. These organic light emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

Materials used as the organic material layer in the organic light-emitting device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions. The light-emitting material includes blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary to realize better natural colors according to the light-emitting color.

In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant may be used as a luminescent material. The principle is that when a small amount of a dopant having an energy band gap smaller than that of a host that mainly constitutes the light emitting layer is mixed with the light emitting layer, excitons generated from the host are transported as a dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

In order to fully exhibit the excellent characteristics of the organic light emitting device described above, materials that form the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc., are supported by stable and efficient materials. The development of new materials continues to be required.

Korean Patent Publication No. 10-2015-0086084

In the present specification, a compound and an organic light emitting device including the same are described.

An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

X1 and X2 are the same as or different from each other, and each independently C or Si,

Ar1 and Ar2 combine with each other to form a substituted or unsubstituted ring,

Ar3 and Ar4 combine with each other to form a substituted or unsubstituted ring,

R1 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In addition, according to an exemplary embodiment of the present specification, 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 at least one of the organic material layers includes the above-described compound.

When the compound of the present invention is used as an organic material layer material of an organic light-emitting device, it is possible to manufacture an organic light-emitting device having a low driving voltage and excellent efficiency and lifetime characteristics. In particular, when the compound of the present invention is used as a dopant for a light emitting layer, an organic light emitting device having a high lifespan and excellent performance can be manufactured.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
FIG. 2 shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4 I did it.

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

The present specification provides a compound represented by the following formula (1). Since the compound represented by the following formula (1) has a polycyclic structure including a spiro, since the three-dimensionality is greater than that of the planarity, light cancellation between molecules can be reduced.

In addition, in the case of using the compound of the present invention as a dopant of the light emitting layer according to an example of the present invention, due to the characteristic that the energy value of the high binding molecular orbit is large, electron transfer is easy when used with a host material containing anthracene. There is an advantage. Therefore, when the compound of the present invention is used in an organic material layer of an organic light-emitting device, it is possible to manufacture an organic light-emitting device having excellent color reproducibility, improved efficiency, and excellent lifespan characteristics.

[Formula 1]

In Formula 1,

X1 and X2 are the same as or different from each other, and each independently C or Si,

Ar1 and Ar2 combine with each other to form a substituted or unsubstituted ring,

Ar3 and Ar4 combine with each other to form a substituted or unsubstituted ring,

R1 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

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

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

The term "substituted" 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 as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium (-D); Halogen group; Silyl group; Boron group; Cyano group (-CN); A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or no substituent. For example, "a substituent to which two or more substituents are connected" 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 addition, the "substituent to which two or more substituents are connected" may be a dimethylphenyl group. That is, the dimethylphenyl group can be interpreted as a substituent in which two methyl groups and a phenyl group are connected.

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

In the present specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

In the present specification, the silyl group may be represented by the formula of -SiY1Y2Y3, wherein Y1, Y2 and Y3 are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes trimethylsilyl group (TMS), triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. It is not limited to this.

In the present specification, the boron group may be represented by the formula of -BY4Y5, wherein Y4 and Y5 are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the boron group includes a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, a diphenyl boron group, and a phenyl boron group, but is not limited thereto.

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-oxy And the like, but are not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.

In the present specification, the amine group may be represented by -NY6Y7, and Y6 and Y7 are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heterocyclic group. In addition, the amine group may be represented by an arylamine group, a heteroarylamine group, an arylheteroarylamine group, and the like, and the aryl and heteroaryl are the aryl groups and heteroaryl groups described below.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, an indenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

Spirofluorenyl groups such as,

(9,9-dimethylfluorenyl group), and

It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.

,

등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si, and Se as a hetero atom, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of heterocyclic groups include pyridyl group, pyrrole group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, carbazole group, imidazole group, pyrazole group, dibenzofuranyl group, dibenzothiophenyl group,

,

And the like, but are not limited to these.

In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroaryl group is aromatic.

In this specification, "adjacent" The group may refer to a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on an atom where the corresponding substituent is substituted. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

In the present specification, in a substituted or unsubstituted ring formed by bonding of adjacent groups to each other, "ring" is a hydrocarbon ring; Or it means a heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and the hydrocarbon ring may be selected from examples of the cycloalkyl group or an aryl group, except that the hydrocarbon ring is not monovalent.

In the present specification, description of an aryl group may be applied except that the aromatic hydrocarbon ring is not monovalent.

In the present specification, the heterocycle is an atom other than carbon and contains one or more heteroatoms, and specifically, the heteroatoms include one or more atoms selected from the group consisting of N, O, P, S, Si and Se can do. The heterocycle may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.

According to an exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently C or Si.

According to another exemplary embodiment, X1 and X2 are C.

In another exemplary embodiment, X1 and X2 are Si.

According to another exemplary embodiment, X1 is C, and X2 is Si.

In another exemplary embodiment, X1 is Si, and X2 is C.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 combine with each other to form a substituted or unsubstituted ring.

According to another exemplary embodiment, Ar1 and Ar2 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or to form a substituted or unsubstituted hetero ring.

In another exemplary embodiment, Ar1 and Ar2 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 hetero ring is formed.

According to another exemplary embodiment, Ar1 and Ar2 are bonded to each other to be selected from the group consisting of deuterium, a halogen group, a cyano group (-CN), a silyl group, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group. One or more substituted or unsubstituted hydrocarbon rings; Or deuterium, a halogen group, a cyano group (-CN), a silyl group, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted hetero ring with at least one selected from the group consisting of a substituted or unsubstituted aryl group.

In another exemplary embodiment, Ar1 and Ar2 are bonded to each other to be selected from the group consisting of deuterium, a halogen group, a cyano group (-CN), a silyl group, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group. A substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms with one or more; Or deuterium, a halogen group, a cyano group (-CN), a silyl group, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted hetero ring having 2 to 60 carbon atoms selected from the group consisting of a substituted or unsubstituted aryl group To form.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are bonded to each other to form deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group, and tert -A hydrocarbon ring having 3 to 60 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of a butylphenyl group; Or substituted or unsubstituted with one or more selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group It forms a C2-C60 heterocycle.

In another exemplary embodiment, Ar1 and Ar2 are bonded to each other to form deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert -Cyclopentane unsubstituted or substituted with one or more selected from the group consisting of butylphenyl group; Deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group substituted or unsubstituted cyclo Hexane; Flu, unsubstituted or substituted with one or more selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group Oren; Deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group substituted or unsubstituted di Benzofluorene; Deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group substituted or unsubstituted cyclo Pentadiene; Xanthene unsubstituted or substituted with one or more selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group (xanthene); Substituted or unsubstituted with one or more selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group Cridin; Or it may be any one of the following structures.

The structures may be substituted with one or more selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group. have.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 combine with each other to form a substituted or unsubstituted ring.

According to another exemplary embodiment, Ar3 and Ar4 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or to form a substituted or unsubstituted hetero ring.

In another exemplary embodiment, Ar3 and Ar4 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 hetero ring is formed.

According to another exemplary embodiment, Ar3 and Ar4 are bonded to each other to be selected from the group consisting of deuterium, a halogen group, a cyano group (-CN), a silyl group, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group. One or more substituted or unsubstituted hydrocarbon rings; Or deuterium, a halogen group, a cyano group (-CN), a silyl group, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted hetero ring with at least one selected from the group consisting of a substituted or unsubstituted aryl group.

In another exemplary embodiment, Ar3 and Ar4 are bonded to each other to be selected from the group consisting of deuterium, a halogen group, a cyano group (-CN), a silyl group, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group. A substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms with one or more; Or deuterium, a halogen group, a cyano group (-CN), a silyl group, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted hetero ring having 2 to 60 carbon atoms selected from the group consisting of a substituted or unsubstituted aryl group To form.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are bonded to each other to form deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group, and tert -A hydrocarbon ring having 3 to 60 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of a butylphenyl group; Or substituted or unsubstituted with one or more selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group It forms a C2-C60 heterocycle.

In another exemplary embodiment, Ar3 and Ar4 are bonded to each other to form deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert -Cyclopentane unsubstituted or substituted with one or more selected from the group consisting of butylphenyl group; Deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group substituted or unsubstituted cyclo Hexane; Flu, unsubstituted or substituted with one or more selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group Oren; Deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group substituted or unsubstituted di Benzofluorene; Deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group substituted or unsubstituted cyclo Pentadiene; Xanthene unsubstituted or substituted with one or more selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group (xanthene); Substituted or unsubstituted with one or more selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group Cridin; Or it may be any one of the following structures.

The structures may be substituted with one or more selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert-butylphenyl group. have.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 4.

[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,

X1, X2 and R1 to R12 are the same as defined in Formula 1,

X3 and X4 are the same as or different from each other, and each independently CRR', NR", O or S,

A1 to A16, B1 to B16, R, R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; halogen group; cyano group (-CN); silyl group; boron group; substituted or unsubstituted An alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combined with an adjacent group to form a substituted or unsubstituted ring,

T1 to T8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, A1 to A16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a halogen group, or combine with an adjacent group to form a substituted or unsubstituted ring.

In another exemplary embodiment, A1 to A16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or fluorine (-F), or a substituted or unsubstituted aromatic hydrocarbon ring by bonding with an adjacent group to each other; Or to form a substituted or unsubstituted aromatic hetero ring.

According to another exemplary embodiment, the A1 to A16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or fluorine (-F), a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms by bonding to each other with an adjacent group; Or a substituted or unsubstituted C2 to C60 aromatic heterocycle is formed.

According to another exemplary embodiment, the A1 to A16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or fluorine (-F), substituted or unsubstituted benzene by bonding with adjacent groups to each other; Substituted or unsubstituted naphthalene; Or to form a substituted or unsubstituted pyridine.

In another exemplary embodiment, A1 to A16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or fluorine (-F), or an aromatic hydrocarbon having 6 to 60 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano group (-CN), an alkyl group having 1 to 20 carbon atoms, and a silyl group by bonding with adjacent groups ring; Or deuterium, a cyano group (-CN), a C 1 to C 20 alkyl group, and a substituted or unsubstituted C 2 to C 60 aromatic hetero ring with one or more selected from the group consisting of a silyl group is formed.

According to another exemplary embodiment, the A1 to A16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or fluorine (-F), or one or more selected from the group consisting of deuterium, cyano group (-CN), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group by bonding with adjacent groups A substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; Or an aromatic having 2 to 60 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano group (-CN), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group Form a hetero ring.

According to an exemplary embodiment of the present specification, A1 to A16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or fluorine (-F), or one or more selected from the group consisting of deuterium, cyano group (-CN), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group by bonding with adjacent groups Benzene substituted or unsubstituted with; Naphthalene unsubstituted or substituted with one or more selected from the group consisting of deuterium, cyano group (-CN), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group; Or deuterium, cyano group (-CN), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group to form at least one substituted or unsubstituted pyridine selected from the group consisting of.

According to another exemplary embodiment, any one of A1 and A2 and any one of A3 and A4 are bonded to each other to form a substituted or unsubstituted benzene; Substituted or unsubstituted naphthalene; Or to form a substituted or unsubstituted pyridine.

According to another exemplary embodiment, any one of A5 and A6 and any one of A7 and A8 are bonded to each other to form a substituted or unsubstituted benzene; Substituted or unsubstituted naphthalene; Or to form a substituted or unsubstituted pyridine.

According to another exemplary embodiment, any one of A9 and A10 and any one of A11 and A12 are bonded to each other to form a substituted or unsubstituted benzene; Substituted or unsubstituted naphthalene; Or to form a substituted or unsubstituted pyridine.

According to another exemplary embodiment, any one of A13 and A14 and any one of A15 and A16 are bonded to each other to form a substituted or unsubstituted benzene; Substituted or unsubstituted naphthalene; Or to form a substituted or unsubstituted pyridine.

According to an exemplary embodiment of the present specification, B1 to B16 are the same as or different from each other, and each independently hydrogen or combine with an adjacent group to form a substituted or unsubstituted ring.

In another exemplary embodiment, B1 to B16 are the same as or different from each other, and each independently hydrogen or a substituted or unsubstituted aromatic hydrocarbon ring by bonding with an adjacent group; Or to form a substituted or unsubstituted aromatic hetero ring.

According to another exemplary embodiment, the B1 to B16 are the same as or different from each other, and each independently hydrogen, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms by bonding with an adjacent group; Or a substituted or unsubstituted C2 to C60 aromatic heterocycle is formed.

In another exemplary embodiment, B1 to B16 are the same as or different from each other, and each independently hydrogen, or benzene substituted or unsubstituted by bonding with an adjacent group to each other; Substituted or unsubstituted naphthalene; It forms a substituted or unsubstituted carbazole or a substituted or unsubstituted pyridine.

According to another exemplary embodiment, the B1 to B16 are the same as or different from each other, and each independently hydrogen or benzene by bonding with an adjacent group to each other; naphthalene; Forms carbazole or pyridine.

According to another exemplary embodiment, any one of B1 and B2 and any one of B3 and B4 are substituted or unsubstituted benzene by bonding to each other; Substituted or unsubstituted naphthalene; Or to form a substituted or unsubstituted pyridine.

In another exemplary embodiment, any one of B1 and B2, any one of B3 and B4, and R" are combined with each other to form a substituted or unsubstituted carbazole.

According to another exemplary embodiment, any one of B5 and B6 and any one of B7 and B8 are bonded to each other to form a substituted or unsubstituted benzene; Substituted or unsubstituted naphthalene; Or to form a substituted or unsubstituted pyridine.

In another exemplary embodiment, any one of B5 and B6, any one of B7 and B8, and R" are bonded to each other to form a substituted or unsubstituted carbazole.

According to another exemplary embodiment, any one of B9 and B10 and any one of B11 and B12 are bonded to each other to form a substituted or unsubstituted benzene; Substituted or unsubstituted naphthalene; Or to form a substituted or unsubstituted pyridine.

In another exemplary embodiment, any one of B9 and B10, any one of B11 and B12, and R" are combined with each other to form a substituted or unsubstituted carbazole.

According to another exemplary embodiment, any one of B13 and B14 and any one of B15 and B16 are bonded to each other to form a substituted or unsubstituted benzene; Substituted or unsubstituted naphthalene; Or to form a substituted or unsubstituted pyridine.

In another exemplary embodiment, any one of B13 and B14, any one of B15 and B16, and R" are bonded to each other to form a substituted or unsubstituted carbazole.

In the exemplary embodiment of the present specification, X3 and X4 are the same as or different from each other, and each independently CRR', NR", O or S.

According to an exemplary embodiment of the present specification, R, R'and R" are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group, or a substituted or unsubstituted ring combined with an adjacent group To form.

In another exemplary embodiment, R, R'and R" are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or by bonding with an adjacent group to replace Or to form an unsubstituted ring.

According to another exemplary embodiment, the R, R'and R" are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or by bonding with an adjacent group and substituted Or to form an unsubstituted ring.

In another exemplary embodiment, R, R'and R" are the same as or different from each other, and each independently hydrogen; Or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, or , By bonding with adjacent groups to form a substituted or unsubstituted ring.

In another exemplary embodiment, R, R'and R" are the same as or different from each other, and each independently hydrogen; Or substituted with a methyl group, ethyl group, propyl group, isopropyl group, butyl group or tert-butyl group, or It is an unsubstituted aryl group having 6 to 30 carbon atoms, or combines with an adjacent group to form a substituted or unsubstituted ring.

According to another exemplary embodiment, the R, R'and R" are the same as or different from each other, and each independently hydrogen; substituted or provided with a methyl group, ethyl group, propyl group, isopropyl group, butyl group, or tert-butyl group Cyclic phenyl group; methyl group, ethyl group, propyl group, isopropyl group, butyl group or tert-butyl group substituted or unsubstituted biphenyl group; Or methyl group, ethyl group, propyl group, isopropyl group, butyl group or tert-butyl group substituted Or it is an unsubstituted naphthyl group, or combines with an adjacent group to form a substituted or unsubstituted ring.

According to another exemplary embodiment, the R, R'and R" are the same as or different from each other, and each independently hydrogen; Or a phenyl group unsubstituted or substituted with a tert-butyl group, or substituted or unsubstituted by bonding with an adjacent group To form a ring.

In another exemplary embodiment, R" is hydrogen; or a phenyl group unsubstituted or substituted with a tert-butyl group, or combine with an adjacent group to form a carbazole.

According to an exemplary embodiment of the present specification, T1 to T8 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group.

According to another exemplary embodiment, the T1 to T8 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another exemplary embodiment, the T1 to T8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

According to another exemplary embodiment, the T1 to T8 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; Or a naphthyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 2 is represented by the following Chemical Formula 2-1 or 2-2.

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,

X1, X2 and R1 to R12 are the same as defined in Formula 1,

A21 to A36 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar11 to Ar14 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic hetero ring.

According to an exemplary embodiment of the present specification, A21 to A36 are the same as or different from each other, and each independently hydrogen; Or a halogen group.

According to another exemplary embodiment, the A21 to A36 are the same as or different from each other, and each independently hydrogen; Or fluorine (-F).

According to an exemplary embodiment of the present specification, Ar11 to Ar14 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle.

According to another exemplary embodiment, Ar11 to Ar14 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 aromatic heterocycle.

According to another exemplary embodiment, the Ar11 to Ar14 are the same as or different from each other, and each independently substituted with one or more selected from the group consisting of deuterium, a cyano group (-CN), an alkyl group having 1 to 20 carbon atoms, and a silyl group, or An unsubstituted C6-C60 aromatic hydrocarbon ring; Or deuterium, cyano group (-CN), an alkyl group having 1 to 20 carbon atoms, and an aromatic heteroring having 2 to 60 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of a silyl group.

In another exemplary embodiment, Ar11 to Ar14 are the same as or different from each other, and each independently deuterium, cyano group (-CN), methyl group, propyl group, isopropyl group, butyl group, tert-butyl group, phenyl group Or an aromatic hydrocarbon ring having 6 to 60 carbon atoms unsubstituted or substituted with a trimethylsilyl group; Or deuterium, cyano group (-CN), methyl group, propyl group, isopropyl group, butyl group, tert-butyl group, phenyl group or trimethylsilyl group substituted or unsubstituted C 2 to C 60 aromatic heterocycle.

According to another exemplary embodiment, Ar11 to Ar14 are the same as or different from each other, and each independently deuterium, cyano group (-CN), methyl group, propyl group, isopropyl group, butyl group, tert-butyl group, phenyl group Or benzene unsubstituted or substituted with a trimethylsilyl group; Naphthalene unsubstituted or substituted with deuterium, cyano group (-CN), methyl group, propyl group, isopropyl group, butyl group, tert-butyl group, phenyl group or trimethylsilyl group; Or deuterium, cyano group (-CN), methyl group, propyl group, isopropyl group, butyl group, tert-butyl group, phenyl group or trimethylsilyl group substituted or unsubstituted pyridine.

According to an exemplary embodiment of the present specification, Formula 3 is represented by the following Formula 3-1 or Formula 3-2.

[Formula 3-1]

[Chemical Formula 3-2]

In Formulas 3-1 and 3-2,

X1, X2 and R1 to R12 are the same as defined in Formula 1,

X3 and X4 are the same as defined in Chemical Formula 3,

B21 to B36 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar21 to Ar24 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic hetero ring, and any one of Ar21 to Ar24 may be bonded to R" to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, B21 to B36 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to another exemplary embodiment, the B21 to B36 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, B21 to B36 are hydrogen.

According to an exemplary embodiment of the present specification, Ar21 to Ar24 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted aromatic hetero ring having 2 to 60 carbon atoms, and Ar21 to Ar24 may be bonded to each other with R" to form a substituted or unsubstituted ring.

According to another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms, and Ar21 to Ar24 are combined with R" and substituted or It can form an unsubstituted hetero ring.

In another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and each independently substituted or unsubstituted benzene; Or substituted or unsubstituted naphthalene, Ar21 to Ar24 may be bonded to each other with R" to form a hetero ring.

According to another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and each independently benzene; Or naphthalene, and Ar21 to Ar24 may be combined with R" to form carbazole.

According to an exemplary embodiment of the present specification, R1 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted alkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to another exemplary embodiment, the R1 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, R1 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

According to another exemplary embodiment, the R1 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluorine (-F); Cyano group (-CN); Methyl group; Butyl group; tert-butyl group; A diphenylamine group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms; A halogen group, a cyano group (-CN), an alkyl group having 1 to 20 carbon atoms, or a phenyl group unsubstituted or substituted with a silyl group; A halogen group, a cyano group (-CN), an alkyl group having 1 to 20 carbon atoms, or a biphenyl group unsubstituted or substituted with a silyl group; A naphthyl group unsubstituted or substituted with a halogen group, a cyano group (-CN), an alkyl group having 1 to 20 carbon atoms, or a silyl group; A fluorenyl group unsubstituted or substituted with a halogen group, a cyano group (-CN), an alkyl group having 1 to 20 carbon atoms, or a silyl group; A dibenzofuran group unsubstituted or substituted with a halogen group, a cyano group (-CN), an alkyl group having 1 to 20 carbon atoms, or a silyl group; Or a halogen group, a cyano group (-CN), an alkyl group having 1 to 20 carbon atoms, or a dibenzothiophene group unsubstituted or substituted with a silyl group.

In another exemplary embodiment, R1 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluorine (-F); Cyano group (-CN); Methyl group; Butyl group; tert-butyl group; A diphenylamine group substituted with an alkyl group having 1 to 20 carbon atoms; A phenyl group unsubstituted or substituted with deuterium, fluorine (-F), cyano group (-CN), methyl group, tert-butyl group, trimethylsilyl group or triphenylsilyl group; Biphenyl group unsubstituted or substituted with deuterium, methyl group, tert-butyl group, trimethylsilyl group, or triphenylsilyl group; A naphthyl group unsubstituted or substituted with deuterium, a methyl group, a tert-butyl group, a trimethylsilyl group, or a triphenylsilyl group; A fluorenyl group unsubstituted or substituted with deuterium, a methyl group, a tert-butyl group, a trimethylsilyl group, or a triphenylsilyl group; Dibenzofuran group unsubstituted or substituted with deuterium, methyl group, tert-butyl group, trimethylsilyl group, or triphenylsilyl group; Or a dibenzothiophene group unsubstituted or substituted with deuterium, methyl group, tert-butyl group, trimethylsilyl group, or triphenylsilyl group.

In the exemplary embodiment of the present specification, Formula 1 may be represented by any one of Compounds 1 to 40 below.

The compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by a method described below.

" 대신 "

"를 사용하는 경우 본원 화학식 1에서 Ar1와 Ar2 및 Ar3와 Ar4가 서로 결합하여 헤테로고리를 형성하는 화합물을 얻을 수 있다.For example, the compound of Formula 1 may have a core structure as shown in the following scheme. Substituents may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art. In addition, when a different type of intermediate is used, a compound having a different structure corresponding to Formula 1 may be obtained. For example, in the following preparation example "

" instead "

In the case of using ", Ar1 and Ar2, and Ar3 and Ar4 are bonded to each other to form a heterocycle in Formula 1 herein.

<Reaction Scheme>

In addition, by introducing various substituents into the core structure of the above-described structure, a compound having the inherent characteristics of the introduced substituent can be synthesized. For example, by introducing a substituent mainly used for the hole injection layer material, the hole transport material, the light emitting layer material and the electron transport layer material used in the manufacture of the organic light emitting device into the core structure, it is possible to synthesize a material that satisfies the conditions required by each organic material layer. I can.

In addition, the organic light emitting device according to the present invention 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, wherein at least one of the organic material layers includes the compound of Formula 1.

The organic light-emitting device of the present invention may be manufactured by a conventional method and material of an organic light-emitting device, except that one or more organic material layers are formed by using the above-described compound.

The compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer 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, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a larger number or a smaller number of organic material layers.

In the organic light-emitting device of the present invention, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by Formula 1 above.

In the organic light emitting device of the present invention, the organic material layer may include a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer may include a compound represented by Formula 1 above.

In another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes one or more compounds represented by Formula 1 above.

According to another exemplary embodiment, the emission layer may include a host and a dopant, and may include at least one of the compounds represented by Formula 1 as the dopant.

In another exemplary embodiment, the emission layer may include a host and a dopant, include at least one of the compounds represented by Formula 1 as the dopant, and at least one of the compounds as the host. .

According to another exemplary embodiment, the emission layer includes a host and a dopant, includes at least one of the compounds represented by Formula 1 as the dopant, and includes at least one of the compounds as the host, , May further include an additional dopant and/or host.

In another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 1 as a dopant of the emission layer, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals, or metal compounds May be included as a dopant.

As another example, the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 1 as a dopant of the emission layer, includes a fluorescent host or a phosphorescent host, and can be used together with an iridium-based (Ir) dopant. have.

In the exemplary embodiment of the present specification, the organic light-emitting device is a green organic light-emitting device in which the emission layer includes the compound represented by Formula 1 as a dopant.

According to the exemplary embodiment of the present specification, the organic light-emitting device is a red organic light-emitting device in which the emission layer includes the compound represented by Formula 1 as a dopant.

In another exemplary embodiment, the organic light-emitting device is a blue organic light-emitting device in which the emission layer includes the compound represented by Formula 1 as a dopant.

According to another exemplary embodiment, the organic material layer may include an emission layer, and the emission layer may include a compound represented by Formula 1 as a host of the emission layer.

As another example, the organic material layer may include an emission layer, and the emission layer may include a compound represented by Formula 1 as a host of the emission layer, and may include a dopant.

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

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

The structure of the organic light-emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

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

FIG. 2 shows an organic light emitting diode in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1. The structure is illustrated. In such a structure, the compound may be included in the hole injection layer 5, the hole transport layer 6, the light-emitting layer 7 or the electron transport layer 8.

For example, the organic light-emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and uses a metal or conductive metal oxide or alloy thereof on a substrate. Is formed by depositing an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon through a deposition process or a solution process, and then depositing a material that can be used as a cathode thereon. I can. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and 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: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is 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 are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, etc., but are not limited thereto.

The hole transport material is a material capable of transporting holes from an anode or a hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

The emission layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

Examples of the host material for the light emitting layer include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

The iridium-based complex used as the dopant of the light emitting layer is as follows, but is not limited thereto.

[Ir(piq) ₃ ] [Btp ₂ Ir(acac)]

[Ir(ppy) ₃ ] [Ir(ppy) ₂ (acac)]

[Ir(mpyp) ₃ ] [F ₂ Irpic]

[(F ₂ ppy) ₂ Ir(tmd)] [Ir(dfppz) ₃ ]

　　　

　　　

As the electron transport material, a material capable of receiving electrons well from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.

The electron injection material 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 prevents the movement of excitons generated in the light emitting layer to the hole injection layer, Further, a compound having excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

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

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

Hereinafter, in order to explain the present specification in detail, it will be described in detail with reference to examples. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present application is not construed as being limited to the embodiments described below. The embodiments of the present application are provided to more completely describe the present specification to those of ordinary skill in the art.

< Synthesis example >

Synthesis example 1. [Intermediate A-1- 3] of synthesis

Intermediate A-1-1 (150 g), bis (pinacolato) diboron (128 g), KOAc (68 g) tricyclohexylphosphine [tricyclohexylphosphine] (2.6 g) Pd ( dba) A flask containing ₂ (2.6g) and 1,4-dioxane [1,4-dioxane] (1.3 L) was heated at 110° C. and stirred for 5 hours. The reaction solution was cooled to room temperature, water and aq.NaCl were added to separate the mixture, and then MgSO ₄ (anhydrous) was treated and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (chloform/hexane) to obtain an intermediate A-1-2 (127 g).

Intermediate A-1-2 (120 g), bis (triphenyl-phosphine) palladium [bis (triphenyl-phosphine) palladium] (3.3 g), potassium phosphate (205 g) and 1,4-dioxane A flask containing [1,4-dioxane] (1.8 L) and distilled water (300 mL) was heated at 110° C. and stirred for 12 hours. The reaction solution was cooled to room temperature, water and aq.NH ₄ Cl were added to separate the mixture, and then MgSO ₄ (anhydrous) was treated and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (chloform/hexane) to obtain an intermediate A-1-3 (42 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=421.

Synthesis example 2. [Intermediate A-1- Of 5] synthesis

A flask containing intermediate A-1-3 (40 g), concentrated sulfuric acid (1 ml), acetic acid (50 ml) and chloroform (250 mL) was heated and stirred at 80° C. for 5 hours. After cooling the reaction solution to room temperature, the solvent was removed under reduced pressure and dissolved again in DMF (300 mL). Aq.NaCl (400 mL) was added and stirred for 30 minutes, and the resulting solid was filtered. The filtered solid was purified by recrystallization (Chlorform/hexane) to obtain an intermediate A-1-4 (23 g).

Bromine (27.5 g) was slowly added dropwise to a flask containing intermediate A-1-4 (15 g), acetic acid (20 mL) and DMF (150 mL) using a dropping funnel. After stirring at room temperature for 3 hours, aq.Na ₂ S ₂ O ₃ was added to the reaction solution, stirred for 30 minutes, and the resulting solid was filtered. The filtered solid was purified by recrystallization (Chlorform/hexane) to obtain an intermediate A-1-5 (20.9 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=668.

Synthesis example 3. [Intermediate A-1- 6] of synthesis

In a flask containing 2-bromo-1,1'-biphenyl [2-bromo-1,1'-biphenyl] (4.6g) dissolved in THF (45 mL, anhydrous) cooled to -78℃, n- Then, butyllithium [n-butyllithium] (3.57mL, 2.5M in hexane) was slowly added dropwise and stirred at the same temperature for 30 minutes. Then, intermediate A-1-5 (6g) was added, and the temperature was gradually raised to room temperature, followed by stirring at room temperature for 6 hours. After separating by adding water and aq.NH ₄ Cl, MgSO ₄ (anhydrous) was treated and filtered. The filtered solution was distilled off under reduced pressure, and then dissolved in chloroform (45 mL). Methanesulfonic acid (2.9 mL) was added dropwise to the reaction solution cooled to 0° C. and stirred at room temperature for 12 hours. The reaction solution was cooled to 0°C, neutralized with aq.NaHCO _3, and then the organic layer was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solvent was removed under reduced pressure and purified with recrystallization (ethyl acetate/hexane) to obtain an intermediate A-1-6 (6.5 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=941.

Synthesis example 4. [Compound A- 1] of synthesis

Intermediate A-1-6 (5 g), tetrakis(triphenylphosphine)palladium(0)[tetrakis-(triphenylphosphine)palladium(0)] (4-60 mg), K ₂ CO ₃ (3.7 g), A flask containing 4-fluorophenyl-boronic acid [4-fluorophenyl-boronic acid] (3.4 g), THF (30 ml) and distilled water (10 mL) was heated at 90° C. and stirred for 6 hours. The reaction solution was cooled to room temperature, water and aq.NH ₄ Cl were added to separate the mixture, and then MgSO ₄ (anhydrous) was treated and filtered. The filtered solution was distilled off under reduced pressure, and purified by silica gel column chromatography (developing solution: hexane/toluene = 10/1 (volume ratio)) to obtain compound A-1 (3.2 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=1005.

Synthesis example 5. [Compound A- 2] of synthesis

Synthesis Example 3. Intermediate A-2-1 (14.1 g) was obtained in the same manner as the method of synthesizing Intermediate A-1-6 using Intermediate A-1-5 (13.5 g).

Synthesis Example 4. Compound A-2 (2.9g) was obtained in the same manner as the method of synthesizing Compound A-1 using Intermediate A-2-1 (5g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=1021.

Synthesis example 6. [Compound A- 3] of synthesis

In a flask containing intermediate A-2-1 (7g) dissolved in THF-d8 (20 mL, anhydrous) cooled to -78℃, n-butyllithium (14.3mL, 2.5M in hexane) was added. It was slowly added dropwise and then stirred at the same temperature for 2 hours. Then, deuterium oxide (10mL, anhydrous) was added, and then the temperature was raised to room temperature and stirred at room temperature for 1 hour. After separating the organic layer, it was filtered by treating with MgSO ₄ (anhydrous). The filtered solvent was removed under reduced pressure and purified with recrystallization (toluene/hexane) to obtain compound A-3 (2.1 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=665.

Synthesis example 7. [Compound A- Of 4] synthesis

Synthesis Example 3. Compound A-4 (3.9g) was obtained in the same manner as in the method of synthesizing Intermediate A-1-6 using Intermediate A-1-4 (7g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=631.

Synthesis example 8. [Intermediate B-1- 3] of synthesis

Synthesis Example 1. Intermediate B-1-2 (58.4g) was obtained in the same manner as the method for synthesizing Intermediate A-1-2 using Intermediate B-1-1 (80g).

Synthesis Example 1. Intermediate B-1-3 (8.5 g) was obtained in the same manner as the method for synthesizing Intermediate A-1-3 using Intermediate B-1-2 (57g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=481.

Synthesis example 9. [Intermediate B-1- Of 5] synthesis

Synthesis Example 2 Using Intermediate B-1-3 (18.7g) Intermediate B-1-4 (8.6g) was obtained in the same manner as in the method of synthesizing Intermediate A-1-4.

Synthesis Example 3. Intermediate B-1-5 (11 g) was obtained in the same manner as in the method of synthesizing intermediate A-1-6 using intermediate B-1-4 (8.6 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=661.

Synthesis example 10. [Compound B- 1] of synthesis

A flask containing intermediate B-1-5 (9.5 g), potassium carbonate (6 g), perfluorobutanesulfonyl floride (11 g) and DMF (60 mL) was placed at room temperature. Stir for 2 hours. Distilled water (150 mL) was added and further stirred at room temperature for 1 hour, and then the solid was filtered under reduced pressure. The filtered solid was purified by recrystallization (THF/EtOH) to obtain intermediate B-1-6 (14.7 g).

Intermediate B-1-6 (4.5 g), dibenzofuranyl-4-boronic acid (1.8 g), bis (triphenylphosphine) palladium [bis (triphenylphosphine) palladium] (20 mg), potassium phosphate [potassium phosphate] (2.4 g ) And 1,4-dioxane [1,4-dioxane] (16 ml) and distilled water (4 ml) were heated at 110° C. and stirred for 4 hours. The reaction solution was cooled to room temperature, water and aq.NH ₄ Cl were added to separate the mixture, and then MgSO ₄ (anhydrous) was treated and filtered. The filtered solution was distilled off under reduced pressure and purified by silica gel column chromatography (developing solution: hexane/toluene = 10/1 (volume ratio)) to obtain compound B-1 (1.9 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=961.

Synthesis example 11. [Compound B- 2] of synthesis

Intermediate B-1-6 (4.5 g), di-ortho-tolylamine (1.5 g), bis (triphenylphosphine) palladium (0) [bis (triphenylphosphine) palladium (0 )] (38 mg), potassium phosphate (1.9 g) and toluene (20 ml) were heated at 120° C. and stirred for 12 hours. The reaction solution was cooled to room temperature, water and aq.NH ₄ Cl were added to separate the mixture, and then MgSO ₄ (anhydrous) was treated and filtered. The filtered solution was distilled off under reduced pressure, and purified by silica gel column chromatography (developing solution: hexane/toluene = 10/1 (volume ratio)) to obtain compound B-2 (1.9 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+] = 1019.

Synthesis example 12. [Intermediate C-1- 3] of synthesis

Intermediate C-1-1 (60g) was dissolved in diethyl ether (750 mL) and then cooled to -78°C. To the cooled reaction solution, n-butyllithium (45.3 mL, 2.5M in hexane) was slowly added dropwise and then stirred at the same temperature for 2 hours. CuCl ₂ (45.7g, anhydrous) was added to the reaction solution and stirred at -78°C for 2 hours, then slowly heated to room temperature and stirred for 1 hour. After adding water and stirring for 30 minutes, the organic layer was separated and then treated with MgSO ₄ (anhydrous) and filtered. The filtered solvent was removed under reduced pressure and purified with recrystallization (cyclohexane) to obtain an intermediate C-1-2 (49.5 g).

Intermediate C-1-2 (45 g) was dissolved in THF (600 mL, anhydrous) and then cooled to -78°C. To the cooled reaction solution, n-butyllithium (99.7 mL, 2.5M in hexane) was added. It was slowly added dropwise and then stirred at the same temperature for 2 hours. After adding SM-1 (32.1g), a dichlorosilyl compound, to the reaction solution, the mixture was stirred for an additional hour at the same temperature, slowly raised to room temperature, and stirred at room temperature for 12 hours. After adding water and aq.NH ₄ Cl and stirring for 30 minutes, the organic layer was separated, treated with MgSO ₄ (anhydrous) and filtered. The filtered solvent was removed under reduced pressure and purified by recrystallization (ethylacetate/hexane) to obtain an intermediate C-1-3 (22.3g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=781.

Synthesis example 13. [Intermediate C-1- Of 5] synthesis

Intermediate C-1-3 (20 g) was dissolved in toluene (100 mL), then boron tribromide (12.3 mL) was slowly added dropwise at 0°C, followed by stirring at room temperature for 6 hours. The reaction solution was cooled to 0°C, and aq.Na ₂ S ₂ O ₃ and aq. NaHCO ₃ was added and stirred for 30 minutes. After separating only the organic layer using a separatory funnel, it was filtered by treating with MgSO ₄ (anhydrous). The filtered solution was distilled off under reduced pressure, dissolved in dimethylformamide [DMF] (100 mL), and then perfluorobutanesulfonyl floride (16 g) and potassium carbonate (9.7 g) were added. Then, the mixture was stirred at room temperature for 12 hours. Distilled water (250 mL) was added and further stirred at room temperature for 1 hour, and then the solid was filtered under reduced pressure. The filtered solid was purified by recrystallization (Toluene/hexane) to obtain an intermediate C-1-5 (16.7 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=1583.

Synthesis example 14. [Compound C- 1] of synthesis

Synthesis Example 4. Compound C-1 (2.1g) was obtained in the same manner as the method of synthesizing compound A-1 using intermediate C-1-5 (6g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=1186.

< Example >

Example One.

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000 Å was placed in distilled water dissolved in a dispersant and washed with ultrasonic waves. The detergent was manufactured by Fischer Co., and the distilled water was Millipore Co. Distilled water filtered secondarily with the product's filter was used. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

The compound HAT was thermally vacuum deposited to a thickness of 50 Å on the prepared ITO transparent electrode to form a hole injection layer. 1000Å of the following compound HT-A was vacuum-deposited as a hole transport layer thereon, and 100Å of the compound HT-B was subsequently deposited. On the light-emitting layer, BH-A as a host and A-2 as a dopant were vacuum-deposited to a thickness of 200 Å at 2% by weight.

Then, 300Å of the following compound ET-A and the compound Liq were deposited at a ratio of 1:1, and on this, magnesium (Mg) doped with 10% by weight of silver (Ag) having a thickness of 150Å and aluminum having a thickness of 1,000Å were sequentially By depositing to form a cathode, an organic light emitting device was manufactured.

In the above process, the deposition rate of the organic material was maintained at 1 Å/sec, the deposition rate for LiF was 0.2 Å/sec, and the deposition rate for aluminum was 3 Å/sec to 7 Å/sec.

Example 2.

In Example 1, an organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound B-1 was used instead of Compound A-2.

Example 3.

In Example 1, an organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound B-2 was used instead of Compound A-2.

Example 4.

In Example 1, an organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound C-1 was used instead of Compound A-2.

Example 5.

In Example 3, an organic light-emitting device was manufactured in the same manner as in Example 3, except that Compound A-3 was used instead of Compound BH-A.

Example 6.

In Example 3, an organic light-emitting device was manufactured in the same manner as in Example 3, except that Compound A-4 was used instead of Compound BH-A.

Example 7.

In Example 3, an organic light-emitting device was manufactured in the same manner as in Example 3, except that Compound A-3 was further included (weight ratio of BH-A and A-4 = 7/3).

Comparative example One.

In Example 1, an organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound D-1 was used instead of Compound A-2.

The driving voltage and efficiency of the organic light-emitting device prepared in Examples 1 to 7, and Comparative Example 1 were measured at a current density of 10 mA/cm ² , and the initial luminance was 90% at a current density of 20 mA/cm ² . The time (life) was measured. The results are shown in Table 1 below.

Experimental example Host Dopant 10mA / cm ² 20mA / cm ² Driving voltage (V) Efficiency (cd/A) Life (hr) Example 1 BH-A A-2 4.9 4.9 173 Example 2 BH-A B-1 5.1 5.6 200 Example 3 BH-A B-2 5.6 5.8 205 Example 4 BH-A C-1 5.8 4.7 162 Example 5 A-3 B-2 5.1 6.2 151 Example 6 A-4 B-2 4.9 6.3 78 Example 7 BH-A + A-3 B-2 5.2 6.2 236 Comparative Example 1 BH-A D-1 5.9 2.8 160

From the results of Table 1, it can be seen that Examples 1 to 7 have superior driving voltage, efficiency, and lifetime characteristics of the device than Comparative Example 1.

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

Claims (11)

Compound represented by the following formula 2-2 or 3-2:
[Formula 2-2]

[Chemical Formula 3-2]

In Formulas 2-2 and 3-2,
X1 and X2 are the same as or different from each other, and each independently C or Si,
Ar11 to Ar14 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic hetero ring,
X3 and X4 are the same as or different from each other, and each independently CRR', NR", O or S,
R, R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; halogen group; cyano group; silyl group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or Unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
Ar21 to Ar24 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic hetero ring,
Any one of Ar21 to Ar24 may be combined with R" to form carbazole,
R1 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. delete delete delete The method according to claim 1,
Formula 1 is a compound represented by any one of the following compounds 1 to 4, compounds 8 to 20, and 23 to 40:

. A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to any one of claims 1 and 5 Light-emitting element. The method of claim 6,
The organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound. The method of claim 6,
The organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound. The method of claim 6,
The organic material layer includes an emission layer, and the emission layer includes one or more of the compounds. The method of claim 9,
The emission layer includes a host and a dopant, and an organic light-emitting device comprising at least one of the compounds as the dopant. The method of claim 9,
The emission layer includes a host and a dopant, at least one of the compounds as the dopant, and at least one of the compounds as the host.

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