KR20190085880A - Multicyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a compound represented by Chemical Formula 1 and an organic light emitting device comprising the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a polycyclic compound and an organic light-

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

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound and an organic light emitting device including the same.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, 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 may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The luminescent material has blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color.

Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant can be used as a light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with a light emitting layer in a small amount, the excitons generated in the host are transported as a dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, light of a desired wavelength can be obtained depending on the type of the dopant used.

In order to sufficiently exhibit the excellent characteristics of the organic light emitting device described above, materials constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material and an electron injecting material are supported by stable and efficient materials Development of new materials is continuously required.

Korean Patent Publication No. 10-2015-0086084

In this specification, compounds and organic light emitting devices containing them are described.

An embodiment of the present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

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

Ar1 and Ar2 are bonded to each other to form a substituted or unsubstituted ring,

Ar3 and Ar4 are bonded to each other to form a substituted or unsubstituted ring,

R1 to R12 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; 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.

According to an embodiment of the present invention, there is also provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound described above.

When the compound of the present invention is used as an organic material layer material of an organic light emitting device, an organic light emitting device having a low driving voltage and excellent efficiency and lifetime characteristics can be manufactured. Particularly, when the compound of the present invention is used as a dopant of a light emitting layer, an organic light emitting device having a high lifetime and excellent performance can be produced.

Fig. 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 element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

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

The present invention provides a compound represented by the following formula (1). The compound represented by the following formula (1) has a polycyclic structure including a spiro, so that the stereostructure is larger than the planarity, so that light cancellation between molecules can be reduced.

In addition, when the compound of the present invention is used as a dopant in the light emitting layer according to an example of the present invention, electron transfer is easy when used together with a host material including an anthracene due to a high energy value of a high binding molecular orbital 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, an organic light emitting device having excellent color reproducibility, improved efficiency, and excellent lifetime characteristics can be manufactured.

 [Chemical Formula 1]

In Formula 1,

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

Ar1 and Ar2 are bonded to each other to form a substituted or unsubstituted ring,

Ar3 and Ar4 are bonded to each other to form a substituted or unsubstituted ring,

R1 to R12 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; 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 this specification, when a part is referred to as "including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

In this specification, when a member is located on another member, it 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 substituents herein 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 substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.

As used herein, the term " substituted or unsubstituted "includes deuterium (-D); A 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, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected. The "substituent group to which two or more substituents are connected" may be a dimethylphenyl group. Namely, the dimethylphenyl group can be interpreted as a substituent in which two methyl groups and a phenyl group are connected.

Illustrative examples of such substituents are set forth below, but are not limited thereto.

In this 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 a substituted or unsubstituted aryl group. The silyl group specifically includes a trimethylsilyl group (TMS), a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But is not limited thereto.

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 a substituted or unsubstituted aryl group. Specific examples of the boron group include, but are not limited to, a dimethyl boron group, a diethyl boron group, a t-butyl methyl boron group, a diphenyl boron group, and a phenyl boron group.

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

In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples thereof include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

In the present specification, the amine group may be represented by -NY6Y7, wherein 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 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 groups apply to the aryl group and the heteroaryl group described below.

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

In the present specification, a 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,

,

, A spirofluorenyl group

(9,9-dimethylfluorenyl group), and

(9,9-diphenylfluorenyl group), and the like. However, the present invention is not limited thereto.

,

등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heteroaromatic ring group containing at least one of N, O, P, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophenyl, carbazole, imidazole, pyrazole,

,

And the like, but are not limited thereto.

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

In this specification, "adjacent" The group may mean a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom of the substituent. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

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

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

In the present specification, an explanation on an aryl group except an aromatic hydrocarbon ring is not monovalent can be applied.

In the present specification, the hetero ring includes one or more non-carbon atoms and hetero atoms. Specifically, the hetero atom includes at least one atom selected from the group consisting of N, O, P, S, Si and Se can do. The heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples of the heteroaryl group may be selected except that the aromatic heterocyclic ring is not monovalent.

According to one embodiment of the present disclosure, X1 and X2 are the same or different from each other, and each independently C or Si.

According to another embodiment, X1 and X2 are C.

In another embodiment, X1 and X2 are Si.

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

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

According to one embodiment of the present invention, Ar1 and Ar2 are bonded to each other to form a substituted or unsubstituted ring.

According to another embodiment, Ar1 and Ar2 may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In another embodiment, Ar1 and Ar2 are a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms which are bonded to each other; Or a substituted or unsubstituted C2-C60 heterocycle.

According to another embodiment, Ar1 and Ar2 may be bonded to each other and 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; Or a substituted or unsubstituted heterocycle 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.

In another embodiment, Ar1 and Ar2 are bonded to each other to form a ring 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 hydrocarbon ring having 3 to 60 carbon atoms, substituted or unsubstituted by 1 or more carbon atoms; Or a heterocyclic ring having 2 to 60 carbon atoms, which is substituted or unsubstituted by at least one member 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 .

According to one embodiment of the present invention, Ar1 and Ar2 are bonded to each other to form a ring structure containing at least one group selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, A hydrocarbon ring having 3 to 60 carbon atoms which is unsubstituted or substituted with at least one group selected from the group consisting of a methyl group, an ethyl group, a propyl group, and a butyl group; Or a substituted or unsubstituted aryl group optionally substituted by one or more groups selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert- To form a heterocycle having 2 to 60 carbon atoms.

In another embodiment, Ar1 and Ar2 may combine with each other to form a ring selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, -Butylphenyl group, or a cyclopentane that is substituted or unsubstituted with at least one member selected from the group consisting of: A substituted or unsubstituted cycloalkyl group selected from the group consisting of hydrogen, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert- Hexane; Substituted or unsubstituted fluids 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- Ore; Substituted or unsubstituted diesters 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- Benzofluorene; A substituted or unsubstituted cycloalkyl group selected from the group consisting of hydrogen, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert- Pentadienes; (S) selected from the group consisting of hydrogen, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert- xanthene; A substituted or unsubstituted aryl group selected from the group consisting of hydrogen, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert- Cridine; Or may be any of the following structures.

The structures may be substituted with at least one member 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- have.

According to one embodiment of the present invention, Ar3 and Ar4 are bonded to each other to form a substituted or unsubstituted ring.

According to another embodiment, Ar3 and Ar4 may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In another embodiment, Ar 3 and Ar 4 are a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms bonded to each other; Or a substituted or unsubstituted C2-C60 heterocycle.

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

In another embodiment, Ar3 and Ar4 are bonded to each other to form a ring 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 hydrocarbon ring having 3 to 60 carbon atoms, substituted or unsubstituted by 1 or more carbon atoms; Or a heterocyclic ring having 2 to 60 carbon atoms, which is substituted or unsubstituted by at least one member 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 .

According to one embodiment of the present invention, Ar3 and Ar4 are bonded to each other to form a ring structure containing at least one selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, A hydrocarbon ring having 3 to 60 carbon atoms which is unsubstituted or substituted with at least one group selected from the group consisting of a methyl group, an ethyl group, a propyl group, and a butyl group; Or a substituted or unsubstituted aryl group optionally substituted by one or more groups selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert- To form a heterocycle having 2 to 60 carbon atoms.

In another embodiment, Ar3 and Ar4 may combine with each other to form a ring selected from the group consisting of deuterium, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, -Butylphenyl group, or a cyclopentane that is substituted or unsubstituted with at least one member selected from the group consisting of: A substituted or unsubstituted cycloalkyl group selected from the group consisting of hydrogen, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert- Hexane; Substituted or unsubstituted fluids 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- Ore; Substituted or unsubstituted diesters 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- Benzofluorene; A substituted or unsubstituted cycloalkyl group selected from the group consisting of hydrogen, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert- Pentadienes; (S) selected from the group consisting of hydrogen, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert- xanthene; A substituted or unsubstituted aryl group selected from the group consisting of hydrogen, fluorine (-F), cyano group (-CN), trimethylsilyl group, methyl group, isopropyl group, tert-butyl group, phenyl group and tert- Cridine; Or may be any of the following structures.

The structures may be substituted with at least one member 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- have.

According to one embodiment of the present invention, the formula (1) is represented by any one of the following formulas (2) to (4).

(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,

X1, X2 and R1 to R12 are as defined in formula (1)

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

A halogen atom, a cyano group (-CN), a silyl group, a boron group, a substituted or unsubstituted aliphatic group, a substituted or unsubstituted aliphatic group, a substituted or unsubstituted aliphatic 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, or is bonded to an adjacent group to form a substituted or unsubstituted ring,

T1 to T8 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A 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 one embodiment of the present invention, A1 to A16 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Or a halogen group, or combine with adjacent groups to form a substituted or unsubstituted ring.

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

According to another embodiment, A1 to A16 are the same or different and each independently hydrogen; heavy hydrogen; Or fluorine (-F), or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms bonded to adjacent groups; Or a substituted or unsubstituted aromatic heterocycle having 2 to 60 carbon atoms.

According to another embodiment, A1 to A16 are the same or different and each independently hydrogen; heavy hydrogen; Or fluorine (-F), or a substituted or unsubstituted benzene bonded to adjacent groups; Substituted or unsubstituted naphthalene; Or a substituted or unsubstituted pyridine.

In another embodiment, A1 to A16 are the same or different from each other and each independently hydrogen; heavy hydrogen; Or an aromatic hydrocarbon having 6 to 60 carbon atoms, which is substituted or unsubstituted with at least one group selected from the group consisting of deuterium, cyano (-CN), alkyl group having 1 to 20 carbon atoms, and silyl group bonded to adjacent groups, ring; Or an aromatic heterocyclic ring having 2 to 60 carbon atoms, which is substituted or unsubstituted with at least one member selected from the group consisting of deuterium, cyano (-CN), an alkyl group having 1 to 20 carbon atoms, and a silyl group.

According to another embodiment, A1 to A16 are the same or different and each independently hydrogen; heavy hydrogen; Or fluorine (-F), or may combine with adjacent groups to form at least one group selected from the group consisting of deuterium, cyano (-CN), methyl, ethyl, propyl, isopropyl, butyl, A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or an aromatic group having 2 to 60 carbon atoms, which is unsubstituted or substituted with at least one group selected from the group consisting of deuterium, cyano (-CN), methyl, ethyl, propyl, isopropyl, butyl, To form a heterocyclic ring.

According to one embodiment of the present invention, A1 to A16 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Or fluorine (-F), or may combine with adjacent groups to form at least one group selected from the group consisting of deuterium, cyano (-CN), methyl, ethyl, propyl, isopropyl, butyl, Substituted or unsubstituted benzene; Naphthalene substituted or unsubstituted with at least one member selected from the group consisting of hydrogen, deuterium, cyano (-CN), methyl, ethyl, propyl, isopropyl, butyl, tert-butyl and trimethylsilyl; Or a substituted or unsubstituted pyridine selected from the group consisting of deuterium, cyano (-CN), methyl, ethyl, propyl, isopropyl, butyl, tert-butyl and trimethylsilyl.

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

According to another 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 a substituted or unsubstituted pyridine.

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

According to another 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 a substituted or unsubstituted pyridine.

According to one embodiment of the present invention, B1 to B16 are the same or different from each other, and are each independently hydrogen or a bond with adjacent groups to form a substituted or unsubstituted ring.

In another embodiment, B1 to B16 are the same or different and each independently hydrogen or a substituted or unsubstituted aromatic hydrocarbon ring bonded to adjacent groups to form an aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle.

According to another embodiment, B1 to B16 are the same or different and each independently hydrogen or an aromatic hydrocarbon ring having 6 to 60 carbon atoms substituted or unsubstituted by bonding to adjacent groups; Or a substituted or unsubstituted aromatic heterocycle having 2 to 60 carbon atoms.

In another embodiment, B1 to B16 are the same or different and each independently hydrogen or a substituted or unsubstituted benzene bonded to adjacent groups; Substituted or unsubstituted naphthalene; Substituted or unsubstituted carbazole or substituted or unsubstituted pyridine.

According to another embodiment, B1 to B16 are the same or different from each other and each independently hydrogen or a group bonded to adjacent groups to form benzene; naphthalene; Carbazole or pyridine.

According to another embodiment, any one of B1 and B2 and any one of B3 and B4 may be bonded to each other to form a substituted or unsubstituted benzene; Substituted or unsubstituted naphthalene; Or a substituted or unsubstituted pyridine.

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

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

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

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

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

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

According to one embodiment of the present invention, R, R 'and R "are the same or different and are each independently hydrogen or a substituted or unsubstituted aryl group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring .

In another embodiment, R, R 'and R "are the same or different and each independently represents hydrogen or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, Or an unsubstituted ring.

According to another embodiment, R, R 'and R "are the same or different and each independently represents hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, Or an unsubstituted ring.

In another embodiment, R, R 'and R "are the same or different and each independently represents hydrogen or an aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms , And the adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

In another embodiment, R, R 'and R "are the same or different and are each independently hydrogen or a substituted or unsubstituted or substituted one or more substituents selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl or tert- An unsubstituted aryl group having 6 to 30 carbon atoms, or is bonded to adjacent groups to form a substituted or unsubstituted ring.

According to another embodiment, R, R 'and R "are the same or different and are each independently hydrogen, substituted or unsubstituted with methyl, ethyl, propyl, isopropyl, butyl or tert- A substituted or unsubstituted biphenyl group with a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or a tert-butyl group or a biphenyl group substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or a tert- Or an unsubstituted naphthyl group, or may combine with adjacent groups to form a substituted or unsubstituted ring.

According to another embodiment, R, R 'and R "are the same or different and each independently represents a phenyl group substituted or unsubstituted with hydrogen or a tert-butyl group, To form a ring.

In another embodiment, R "is a phenyl group substituted or unsubstituted with hydrogen or a tert-butyl group, or combines with adjacent groups to form a carbazole.

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

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

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

According to one embodiment of the present invention, the formula (2) is represented by the following formula (2-1) or (2-2).

[Formula 2-1]

[Formula 2-2]

In the above Formulas (2-1) and (2-2)

X1, X2 and R1 to R12 have the same definitions as in the above formula (1)

A21 to A36 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A 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 or different and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle.

According to one embodiment of the present invention, A21 to A36 are the same or different and each independently hydrogen; Or a halogen group.

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

According to one embodiment of the present invention, Ar11 to Ar14 are the same or different and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle.

According to another embodiment, Ar11 to Ar14 may be the same or different and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 60 carbon atoms.

According to another embodiment, Ar11 to Ar14 are the same or different and are each independently substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, cyano (-CN), alkyl having 1 to 20 carbon atoms, and silyl An unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or an aromatic heterocyclic ring having 2 to 60 carbon atoms, which is substituted or unsubstituted with at least one member selected from the group consisting of deuterium, cyano (-CN), an alkyl group having 1 to 20 carbon atoms, and a silyl group.

 In another embodiment, Ar11 to Ar14 may be the same or different and each independently selected from the group consisting of deuterium, a cyano group (-CN), a methyl group, a propyl group, an isopropyl group, a butyl group, Or an aromatic hydrocarbon ring of 6 to 60 carbon atoms which is substituted or unsubstituted with a trimethylsilyl group; Or an aromatic heterocycle having 2 to 60 carbon atoms which is substituted or unsubstituted with deuterium, a cyano group (-CN), a methyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a phenyl group or a trimethylsilyl group.

According to another embodiment, Ar11 to Ar14 may be the same or different from each other and each independently selected from the group consisting of deuterium, a cyano group (-CN), a methyl group, a propyl group, an isopropyl group, a butyl group, Benzene substituted or unsubstituted with trimethylsilyl group; Naphthalene substituted or unsubstituted with deuterium, cyano (-CN), methyl, propyl, isopropyl, butyl, tert-butyl, phenyl or trimethylsilyl; Or pyridine substituted or unsubstituted with deuterium, cyano group (-CN), methyl group, propyl group, isopropyl group, butyl group, tert-butyl group, phenyl group or trimethylsilyl group.

According to one embodiment of the present invention, the formula (3) is represented by the following formula (3-1) or (3-2).

[Formula 3-1]

[Formula 3-2]

In the above Formulas (3-1) and (3-2)

X1, X2 and R1 to R12 have the same definitions as in the above formula (1)

X3 and X4 have the same definitions as in the above formula (3)

B21 to B36 are the same or different and each independently hydrogen; heavy hydrogen; A 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 or different and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocyclic ring, and any one of Ar21 to Ar24 may be bonded to R "to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, B21 to B36 are the same or different and are each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to another embodiment, B21 to B36 are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, B21 to B36 are hydrogen.

According to one embodiment of the present invention, Ar 21 to Ar 24 are the same or different and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 60 carbon atoms, and Ar 21 to Ar 24 may be bonded to each other to form a substituted or unsubstituted ring.

According to another embodiment, Ar 21 to Ar 24 are the same or different and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms, and Ar 21 to Ar 24 may be bonded to each other to form a substituted or unsubstituted To form an unsubstituted heterocycle.

In another embodiment, Ar 21 to Ar 24 are the same or different and are each independently substituted or unsubstituted benzene; Or substituted or unsubstituted naphthalene, and Ar21 to Ar24 may be bonded to each other to form a heterocycle.

According to another embodiment, Ar 21 to Ar 24 are the same or different from each other, and each independently represents benzene; Or naphthalene, and Ar 21 to Ar 24 may combine with R "to form a carbazole.

According to one embodiment of the present invention, R1 to R12 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A 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 embodiment, R 1 to R 12 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano group (-CN); A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; 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 heteroaryl group having 2 to 60 carbon atoms.

In another embodiment, R 1 to R 12 are the same or different and each independently hydrogen; heavy hydrogen; A 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 dibenzofurane group; Or a substituted or unsubstituted dibenzothiophene group.

According to another embodiment, R 1 to R 12 are the same or different and each independently hydrogen; heavy hydrogen; Fluorine (-F); Cyano group (-CN); Methyl group; Butyl group; tert-butyl group; A diphenylamine group substituted or unsubstituted 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 substituted or unsubstituted with a silyl group; A halogen group, a cyano group (-CN), an alkyl group having 1 to 20 carbon atoms, or a biphenyl group substituted or unsubstituted with a silyl group; A halogen group, a cyano group (-CN), an alkyl group having 1 to 20 carbon atoms, or a naphthyl group substituted or unsubstituted with a silyl group; A halogen group, a cyano group (-CN), an alkyl group having 1 to 20 carbon atoms or a fluorenyl group substituted or unsubstituted with a silyl group; A halogen group, a cyano group (-CN), an alkyl group having 1 to 20 carbon atoms, or a dibenzofurane group substituted or unsubstituted with a silyl group; Or a dibenzothiophene group substituted or unsubstituted with a halogen group, a cyano group (-CN), an alkyl group having 1 to 20 carbon atoms, or a silyl group.

In another embodiment, R 1 to R 12 are the same or different 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 substituted or unsubstituted with deuterium, fluorine (-F), cyano group (-CN), methyl group, tert-butyl group, trimethylsilyl group or triphenylsilyl group; A biphenyl group substituted or unsubstituted with a deuterium, a methyl group, a tert-butyl group, a trimethylsilyl group or a triphenylsilyl group; A naphthyl group substituted or unsubstituted with a deuterium, a methyl group, a tert-butyl group, a trimethylsilyl group or a triphenylsilyl group; A fluorenyl group substituted or unsubstituted with a deuterium, a methyl group, a tert-butyl group, a trimethylsilyl group or a triphenylsilyl group; A dibenzofurane group substituted or unsubstituted with a deuterium, a methyl group, a tert-butyl group, a trimethylsilyl group or a triphenylsilyl group; Or a dibenzothiophene group substituted or unsubstituted with a deuterium, a methyl group, a tert-butyl group, a trimethylsilyl group or a triphenylsilyl group.

In one embodiment of the present invention, the formula (1) may be represented by any one of the following compounds 1 to 40.

The compound of formula (1) according to one embodiment of the present invention can be prepared by the following production method.

" 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) can be prepared into a core structure as shown in the following reaction formula. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art. Further, when another kind of intermediate is used, compounds of other structures corresponding to the above formula (1) can be obtained. For example, in the following production example, "

" instead "

, A compound in which Ar1 and Ar2 and Ar3 and Ar4 are bonded to each other to form a heterocyclic ring can be obtained.

<Reaction Scheme>

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent mainly used in a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic light emitting device into the core structure, a material meeting the requirements of each organic layer is synthesized .

Further, the organic light emitting device according to the present invention includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1.

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

The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, 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 injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include more or fewer organic 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 the above formula (1).

In the organic light emitting device of the present invention, the organic material layer may include a hole injecting layer or a hole transporting layer, and the hole injecting layer or the hole transporting layer may include the compound represented by the above formula (1).

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes one or more compounds represented by the general formula (1).

According to another embodiment, the light emitting layer includes a host and a dopant, and at least one of the compounds represented by Formula 1 may be included as the dopant.

In another embodiment, the light emitting layer includes a host and a dopant, and at least one of the compounds represented by Formula 1 may be included as the dopant, and at least one of the compounds may be included as the host .

According to another embodiment, the light emitting layer comprises a host and a dopant, wherein at least one of the compounds represented by Formula 1 is included as the dopant, at least one of the compounds is included as the host, , An additional dopant and / or a host.

In another embodiment, the organic layer includes a light-emitting layer, wherein the light-emitting layer contains a compound represented by the general formula (1) as a dopant of the light-emitting layer and includes a fluorescent host or a phosphorescent host, As a dopant.

As another example, the organic layer may include a light emitting layer, and the light emitting layer may include a compound represented by Formula 1 as a dopant of the light emitting layer, and may include a fluorescent host or a phosphorescent host, and may be used together with an iridium (Ir) have.

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

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

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

According to another embodiment, the organic layer may include a light emitting layer, and the light emitting layer may include a compound represented by Formula 1 as a host of the light emitting layer.

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

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

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

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

1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated on a substrate 1. In FIG. In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic light emitting device in which an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 are sequentially laminated on a substrate 1 Structure is illustrated. In such a structure, the compound may be included in the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 7, or the electron transporting layer 8.

For example, the organic light emitting device according to the present invention may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate, To form an anode, an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed thereon through a deposition process or a solution process, and then a substance which can be used as a cathode is deposited thereon . In addition to such a 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.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted 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; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The negative electrode 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; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting layer may emit red, green or blue light, and may be formed of a phosphor or a fluorescent material. The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

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

The iridium complex used as a dopant in 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 transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. Specific examples include an 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 injecting material has an ability to transport electrons, has an electron injecting effect from the cathode, an electron injecting effect to the emitting layer or the light emitting material, prevents migration of excitons generated in the emitting layer to the hole injecting layer, Further, a compound having excellent thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injection layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

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

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other 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 enable those skilled in the art to more fully understand the present invention.

< Synthetic example >

Synthetic example  1. [Intermediate A-1- 3]  synthesis

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

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

Synthetic example  2. [Intermediate A-1- 5]  synthesis

The flask containing the 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. The reaction solution was cooled to room temperature, the solvent was removed under reduced pressure, and the residue was dissolved again in DMF (300 mL). aq. NaCl (400 mL) was added, stirred for 30 minutes, and the resulting solid was filtered. The filtered solid was purified by recrystallization (Chlorform / hexane) to obtain intermediate A-1-4 (23 g).

Bromine [bromine] (27.5 g) was slowly added dropwise to the flask containing the 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 intermediate A-1-5 (20.9 g). As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M + H +] = 668.

Synthetic example  3. [Intermediate A-1- 6]  synthesis

To a flask containing 2-bromo-1,1'-biphenyl (4.6 g) dissolved in THF (45 mL, anhydrous) cooled to -78 ° C was added n- Butyl lithium [n-butyllithium] (3.57 mL, 2.5 M in hexane) was slowly added dropwise and then stirred at the same temperature for 30 minutes. Intermediate A-1-5 (6 g) was then added, the temperature was gradually raised to room temperature, and the mixture was stirred at room temperature for 6 hours. Water and aq.NH ₄ Cl were added to the solution, which was then filtered through MgSO ₄ (anhydrous). The filtered solution was distilled off under reduced pressure and dissolved in chloroform (45 mL). Methanesulfonic acid (2.9 mL) was added dropwise to the reaction solution cooled to 0 占 폚, and then stirred at room temperature for 12 hours. The reaction solution was cooled to 0 ° C and neutralized with aq. NaHCO _{3. The} organic layer was separated, treated with MgSO ₄ (anhydrous) and filtered. The filtered solvent was removed under reduced pressure and the residue was purified by recrystallization (ethyl acetate / hexane) to obtain Intermediate A-1-6 (6.5 g). As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M + H +] = 941.

Synthetic example  4. [Compound A- 1]  synthesis

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

Synthetic example  5. [Compound A- 2]  synthesis

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

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

Synthetic example  6. [Compound A- 3]  synthesis

N-butyllithium (14.3 mL, 2.5 M in hexane) was added to the intermediate-sized A-2-1 (7 g) bottom long flask dissolved in THF-d8 (20 mL, anhydrous) The mixture was slowly added dropwise and stirred at the same temperature for 2 hours. Then, deuterium oxide (10 mL, anhydrous) was added and the temperature was raised to room temperature, followed by stirring at room temperature for 1 hour. The organic layer was separated and treated with MgSO ₄ (anhydrous). The filtered solvent was removed under reduced pressure and the residue was purified by recrystallization (toluene / hexane) to obtain Compound A-3 (2.1 g). As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M + H +] = 665.

Synthetic example  7. [Compound A- 4]  synthesis

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

Synthetic example  8. [Preparation of intermediate B-1- 3]  synthesis

Intermediate B-1-1 (80 g) Synthesis Example 1. Intermediate B-1-2 (58.4 g) was obtained in the same manner as in the synthesis of Intermediate A-1-2.

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

Synthetic example  9. [Preparation of intermediate B-1- 5]  synthesis

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

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

Synthetic example  10. [Compound B- 1]  synthesis

A flask containing the intermediate B-1-5 (9.5 g), potassium carbonate (6 g), perfluorobutanesulfonyl fluoride (11 g) and DMF (60 mL) And stirred for 2 hours. Distilled water (150 mL) was further added, and the mixture was further stirred at room temperature for 1 hour, followed by vacuum filtration. The filtered solid was purified by recrystallization (THF / EtOH) to give Intermediate B-1-6 (14.7 g)

(1.8 g), bis (triphenylphosphine) palladium (20 mg), potassium phosphate [potassium phosphate (2.4 g), and triethylamine ) 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, separated by adding water and aq. NH ₄ Cl, treated with MgSO ₄ (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by silica gel column chromatography (eluent: hexane / toluene = 10/1 (by volume)) to obtain Compound B-1 (1.9 g). As a result of measurement of the mass spectrum of the obtained solid, a peak was confirmed at [M + H +] = 961.

Synthetic example  11. [Compound B- 2]  synthesis

Intermediate B-1-6 (4.5 g), di-ortho-tolylamine (1.5 g), bis (triphenylphosphine) palladium (0) [bis )] (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, separated by adding water and aq. NH ₄ Cl, treated with MgSO ₄ (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by silica gel column chromatography (eluent: hexane / toluene = 10/1 (by volume)) to obtain Compound B-2 (1.9 g). As a result of measurement of the mass spectrum of the obtained solid, a peak was confirmed at [M + H +] = 1019.

Synthetic example  12. [Intermediate C-1- 3]  synthesis

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

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

Synthetic example  13. [Intermediate C-1- 5]  synthesis

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

Synthetic example  14. [Compound C- 1]  synthesis

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

< Example >

Example  One.

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 Å was immersed in distilled water containing a dispersing agent and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

The compound HAT was thermally vacuum deposited on the ITO transparent electrode to a thickness of 50 Å to form a hole injection layer. Compound HT-A 1000 Å shown below was vacuum-deposited as a hole transport layer thereon, followed by vapor deposition of Compound HT-B 100 Å. BH-A as a host and A-2 as a dopant were vacuum-deposited to a thickness of 200 Å in a thickness of 2 wt% for the light emitting layer.

Next, 300 Å of the following compound ET-A and the compound Liq were deposited in a ratio of 1: 1, magnesium (Mg) doped with 10 wt% of silver and magnesium of 1,000 Å were sequentially deposited thereon. To form a cathode, thereby preparing an organic light emitting device.

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

Example  2.

An organic luminescent device was prepared in the same manner as in Example 1, except that the compound B-1 was used instead of the compound A-2.

Example  3.

An organic luminescent device was prepared in the same manner as in Example 1, except that Compound B-2 was used instead of Compound A-2.

Example  4.

An organic luminescent device was prepared in the same manner as in Example 1, except that the compound C-1 was used instead of the compound A-2.

Example  5.

An organic luminescent device was prepared in the same manner as in Example 3, except that the compound A-3 was used instead of the compound BH-A.

Example  6.

An organic luminescent device was prepared in the same manner as in Example 3, except that the compound A-4 was used instead of the compound BH-A.

Example  7.

An organic luminescent device was prepared in the same manner as in Example 3, except that Compound A-3 was further contained (weight ratio of BH-A and A-4 = 7/3).

Comparative Example  One.

An organic luminescent device was prepared in the same manner as in Example 1 except that the following compound D-1 was used instead of the compound A-2.

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

Experimental Example Host Dopant 10 mA / cm ² 20 mA / cm ² The 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 shown in Table 1, it can be confirmed that the devices of Examples 1 to 7 are superior in driving voltage, efficiency, and lifetime characteristics to those of Comparative Example 1.

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

Claims (11)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
X1 and X2 are the same or different and each independently C or Si,
Ar1 and Ar2 are bonded to each other to form a substituted or unsubstituted ring,
Ar3 and Ar4 are bonded to each other to form a substituted or unsubstituted ring,
R1 to R12 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; 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. The method according to claim 1,
(1) is a compound represented by any one of the following formulas (2) to (4):
(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,
X1, X2 and R1 to R12 are as defined in formula (1)
X3 and X4 are the same or different and each independently CRR ', NR &quot;, O or S,
A halogen atom, a cyano group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, An unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring,
T1 to T8 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; 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. The method of claim 2,
(2) is a compound represented by the following formula (2-1) or (2-2): &lt; EMI ID =
[Formula 2-1]

[Formula 2-2]

In the above Formulas (2-1) and (2-2)
X1, X2 and R1 to R12 have the same definitions as in the above formula (1)
A21 to A36 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; 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 or different and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle. The method of claim 2,
Wherein the compound represented by Formula 3 is represented by Formula 3-1 or 3-2:
[Formula 3-1]

[Formula 3-2]

In the above Formulas (3-1) and (3-2)
X1, X2 and R1 to R12 have the same definitions as in the above formula (1)
X3 and X4 have the same definitions as in the above formula (3)
B21 to B36 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; 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 or different and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocyclic ring, and any one of Ar21 to Ar24 may be bonded to R "to form a substituted or unsubstituted ring. The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following compounds 1 to 40:

. A first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound according to any one of claims 1 to 5. The organic light- Light emitting element. The method of claim 6,
Wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound. The method of claim 6,
Wherein the organic material layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer comprises the compound. The method of claim 6,
Wherein the organic material layer includes a light emitting layer, and the light emitting layer includes one or more of the compounds. The method of claim 9,
Wherein the light emitting layer comprises a host and a dopant, and at least one of the compounds is included as the dopant. The method of claim 9,
Wherein the light emitting layer comprises a host and a dopant, wherein at least one of the compounds is contained as the dopant, and at least one of the compounds is included as the host.

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