KR102141293B1 - 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

Polycyclic compound and an organic light emitting device comprising the same{MULTICYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

This specification claims the benefit of Korean Patent Application No. 10-2018-0003776 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 emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode and electrons are injected at the cathode, and excitons are formed when the injected holes meet the electrons. When it falls to the ground again, it will shine. It is known that such an organic light emitting device has characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.

Materials used as the organic material layer in the organic light emitting device may 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, depending on their function. The light emitting materials include blue, green, and red light emitting materials, and yellow and orange light emitting materials necessary for realizing a better natural color depending on the light emitting color.

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

In order to sufficiently exhibit the excellent characteristics of the above-described organic light-emitting device, a material forming an organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., are supported by stable and efficient materials. Development of new materials continues to be required.

Korean Patent Publication No. 10-2015-0086084

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

One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[Formula 1]

In Chemical Formula 1,

X1 and X2 are the same as or different from each other, and each independently O, S, CRaRb, NRc or SiRdRe,

Ra, Rb, Rc, Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

One or more of R1 to R12 are each independently a cyano group (-CN); Boron group; Silyl 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 rest is hydrogen or deuterium.

In addition, according to an exemplary embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the above-described compound.

When the compound of the present invention is used as an organic material layer material for an organic light emitting device, an organic light emitting device having excellent efficiency and life characteristics can be manufactured.

1 shows an example of an organic light emitting device including 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 comprising 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 It is done.

Hereinafter, this specification will be described in more detail.

The present specification provides a compound represented by Formula 1 below. Since the compound represented by the following Chemical Formula 1 has a larger three-dimensionality than planarity, light cancellation between molecules can be reduced. In particular, when X1 and X2 in the following Chemical Formula 1 are heteroatoms, it is possible to maintain a more three-dimensional molecular skeleton due to repulsion of non-covalent electron pairs. In addition, the non-covalent electron pair of the hetero atom increases the mobility of the hole, so that the balance between the hole and the electron is improved, and low voltage and long life characteristics can be expected.

In addition, when the compound of the present invention is used as a dopant in a light emitting layer according to an example of the present invention, electron transfer is easy when used with a host material containing anthracene due to its high energy value of high binding molecular orbit. 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 lifespan characteristics can be manufactured.

[Formula 1]

In Chemical Formula 1,

X1 and X2 are the same as or different from each other, and each independently O, S, CRaRb, NRc or SiRdRe,

Ra, Rb, Rc, Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

One or more of R1 to R12 are each independently a cyano group (-CN); Boron group; Silyl 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 rest is hydrogen or deuterium.

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

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

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

The term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent is substitutable, and when two or more are substituted , 2 or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" in this specification is deuterium; Halogen group; 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 substituted or unsubstituted heterocyclic groups, substituted with 1 or 2 or more substituents selected from the group, or substituted with 2 or more substituents among the exemplified substituents, or having no substituents. For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected. In addition, "substituents linked to two or more substituents" may be a tert-butylphenyl group. That is, the tert-butylphenyl group may be interpreted as a substituent in which a tert-butyl group and a phenyl group are connected.

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

In the present specification, the silyl group may be represented by the formula -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 a trimethylsilyl group (TMS), a triethylsilyl group, a tert-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc. It is not limited to this.

In the present specification, the boron group may be represented by the formula -BY4Y5, wherein Y4 and Y5 are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group is specifically dimethyl boron group, diethyl boron group, tert-butyl methyl boron group, diphenyl boron group, phenyl boron group, and the like, but is not limited thereto.

In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 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 are 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-ox Tilgi, and the like, but are not limited to these.

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

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 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, etc., and the aryl group and heteroaryl group described later apply to the aryl group and heteroaryl group.

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 one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, indenyl group, phenanthrenyl group, pyrenyl group, perylene group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may combine with 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 hetero atom and is a ring group containing one or more of N, O, P, S, Si, and Se, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include pyridyl group, pyrrol 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, a description of the aforementioned heterocyclic group may be applied, except that the heteroaryl group is aromatic.

According to an exemplary embodiment of the present specification, one or more of the R1 to R12 are each independently a cyano group (-CN); Boron group; Silyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted amine 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, the rest is hydrogen or deuterium.

According to an exemplary embodiment of the present specification, at least one of the R1 to R12 is not the hydrogen, the above-described substituents are bonded, the compound of the present invention is a compound in which R1 to R12 are both hydrogen and R3 and R4 are combined to form a ring Alternatively, when applied to an organic light emitting device, a device having excellent efficiency and long life characteristics can be obtained compared to a compound in which R9 and R10 are combined to form a ring.

According to another exemplary embodiment, at least one of R1 to R12 is a cyano group (-CN); Silyl group; 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, the rest is hydrogen or deuterium.

In another exemplary embodiment, two or four of the R1 to R12 are cyano groups (-CN); Silyl group; 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, the rest is hydrogen or deuterium.

In another exemplary embodiment, at least one of R1 to R12 is a cyano group (-CN); Silyl group; A substituted or unsubstituted alkyl group having 1 to 30 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, the rest is hydrogen or deuterium.

According to another exemplary embodiment, at least one of R1 to R12 is a cyano group (-CN); Silyl group; A substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, the rest is hydrogen or deuterium.

In another exemplary embodiment, at least one of R1 to R12 is a cyano group (-CN); Trimethylsilyl group; Triphenylsilyl group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted pentyl 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 terphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted pyridyl group; Or a substituted or unsubstituted dibenzothiophenyl group, the rest is hydrogen or deuterium.

In another exemplary embodiment, at least one of R1 to R12 is a cyano group (-CN); Trimethylsilyl group; Triphenylsilyl group; Methyl group; A methyl group substituted with deuterium; Ethyl group; Propyl group; Isopropyl group; Butyl group; tert-butyl group; Pentyl group; diphenylamine group unsubstituted or substituted with tert-butyl group; A phenyl group unsubstituted or substituted with one or more selected from the group consisting of fluorine (-F), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group; A biphenyl group unsubstituted or substituted with one or more selected from the group consisting of fluorine (-F), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group; A naphthyl group unsubstituted or substituted with one or more selected from the group consisting of fluorine (-F), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group; A terphenyl group unsubstituted or substituted with one or more selected from the group consisting of fluorine (-F), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group; A fluorenyl group unsubstituted or substituted with one or more selected from the group consisting of fluorine (-F), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group; Dibenzofuranyl group; Pyridyl group; Or a dibenzothiophenyl group, the rest being hydrogen or deuterium.

According to another exemplary embodiment, at least one of R1 to R12 is a cyano group (-CN); Trimethylsilyl group; Triphenylsilyl group; Methyl group; A methyl group substituted with deuterium; Ethyl group; Propyl group; Isopropyl group; Butyl group; tert-butyl group; Pentyl group; diphenylamine group unsubstituted or substituted with tert-butyl group; A phenyl group unsubstituted or substituted with one or more selected from the group consisting of fluorine (-F), methyl group, tert-butyl group and trimethylsilyl group; A biphenyl group unsubstituted or substituted with one or more selected from the group consisting of a methyl group and a tert-butyl group; A naphthyl group unsubstituted or substituted with one or more selected from the group consisting of a methyl group and a tert-butyl group; A terphenyl group unsubstituted or substituted with 1 or more selected from the group consisting of a methyl group and a tert-butyl group; A fluorenyl group unsubstituted or substituted with one or more selected from the group consisting of methyl groups and tert-butyl groups; Dibenzofuranyl group; Pyridyl group; Or a dibenzothiophenyl group, the rest being hydrogen or deuterium.

According to another exemplary embodiment, at least one of R1 to R12 is a cyano group (-CN); Trimethylsilyl group; Triphenylsilyl group; Methyl group; A methyl group substituted with deuterium; Ethyl group; Propyl group; Isopropyl group; Butyl group; tert-butyl group; Pentyl group; diphenylamine group substituted with tert-butyl group; Ditert-butylphenyl group; Phenyl group; Trifluorophenyl group; Trimethylsilylphenyl group; Biphenyl group; Naphthyl group; Terphenyl group; 9,9-dimethylfluorenyl group; Dibenzofuranyl group; Pyridyl group; Or a dibenzothiophenyl group, the rest being hydrogen or deuterium.

In one embodiment of the present specification, the compound represented by Formula 1 is represented by Formula 2 or 3 below.

[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,

The definitions of X1 and X2 are the same as in Formula 1,

Ar1 to Ar6 are the same as or different from each other, and each independently a cyano group; Boron group; Silyl 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 the exemplary embodiment of the present specification, Ar1 to Ar6 are the same as or different from each other, and each independently a cyano group (-CN); Boron group; Silyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted amine 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.

According to another exemplary embodiment, Ar1 to Ar6 are the same as or different from each other, and each independently a cyano group (-CN); Silyl group; 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.

In another exemplary embodiment, Ar1 to Ar6 are the same as or different from each other, and each independently a cyano group (-CN); Silyl group; A substituted or unsubstituted alkyl group having 1 to 30 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.

According to another exemplary embodiment, Ar1 to Ar6 are the same as or different from each other, and each independently a cyano group (-CN); Silyl group; A substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In another exemplary embodiment, Ar1 to Ar6 are the same as or different from each other, and each independently a cyano group (-CN); Trimethylsilyl group; Triphenylsilyl group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted pentyl 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 terphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted pyridyl group; Or a substituted or unsubstituted dibenzothiophenyl group.

In another exemplary embodiment, Ar1 to Ar6 are the same as or different from each other, and each independently a cyano group (-CN); Trimethylsilyl group; Triphenylsilyl group; Methyl group; A methyl group substituted with deuterium; Ethyl group; Propyl group; Isopropyl group; Butyl group; tert-butyl group; Pentyl group; diphenylamine group unsubstituted or substituted with tert-butyl group; A phenyl group unsubstituted or substituted with one or more selected from the group consisting of fluorine (-F), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group; A biphenyl group unsubstituted or substituted with one or more selected from the group consisting of fluorine (-F), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group; A naphthyl group unsubstituted or substituted with one or more selected from the group consisting of fluorine (-F), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group; A terphenyl group unsubstituted or substituted with one or more selected from the group consisting of fluorine (-F), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group; A fluorenyl group unsubstituted or substituted with one or more selected from the group consisting of fluorine (-F), methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and trimethylsilyl group; Dibenzofuranyl group; Pyridyl group; Or dibenzothiophenyl group.

According to another exemplary embodiment, Ar1 to Ar6 are the same as or different from each other, and each independently a cyano group (-CN); Trimethylsilyl group; Triphenylsilyl group; Methyl group; A methyl group substituted with deuterium; Ethyl group; Propyl group; Isopropyl group; Butyl group; tert-butyl group; Pentyl group; diphenylamine group unsubstituted or substituted with tert-butyl group; A phenyl group unsubstituted or substituted with one or more selected from the group consisting of fluorine (-F), methyl group, tert-butyl group and trimethylsilyl group; A biphenyl group unsubstituted or substituted with one or more selected from the group consisting of a methyl group and a tert-butyl group; A naphthyl group unsubstituted or substituted with 1 or more selected from the group consisting of a methyl group and a tert-butyl group; A terphenyl group unsubstituted or substituted with one or more selected from the group consisting of a methyl group and a tert-butyl group; A fluorenyl group unsubstituted or substituted with one or more selected from the group consisting of methyl groups and tert-butyl groups; Dibenzofuranyl group; Pyridyl group; Or dibenzothiophenyl group.

According to another exemplary embodiment, Ar1 to Ar6 are the same as or different from each other, and each independently a cyano group (-CN); Trimethylsilyl group; Triphenylsilyl group; Methyl group; A methyl group substituted with deuterium; Ethyl group; Propyl group; Isopropyl group; Butyl group; tert-butyl group; Pentyl group; diphenylamine group substituted with tert-butyl group; Ditert-butylphenyl group; Phenyl group; Trifluorophenyl group; Trimethylsilylphenyl group; Biphenyl group; Naphthyl group; Terphenyl group; 9,9-dimethylfluorenyl group; Dibenzofuranyl group; Pyridyl group; Or dibenzothiophenyl group.

According to one embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently O, S, CRaRb, NRc, or SiRdRe.

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

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

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

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

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

According to another exemplary embodiment, one of X1 and X2 is S, and the other is O.

According to an exemplary embodiment of the present specification, the Ra, Rb, Rc, Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 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.

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

According to another exemplary embodiment, Ra and Rb are the same as or different from each other, and each independently substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another exemplary embodiment, Ra and Rb are the same as or different from each other, and each independently 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 exemplary embodiment, Ra and Rb are the same as or different from each other, and each independently an alkyl group having 1 to 20 carbon atoms; Or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, Ra and Rb are the same as or different from each other, and each independently a methyl group; Or a phenyl group unsubstituted or substituted with one or more selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl and tert-butyl groups.

In another exemplary embodiment, Ra and Rb are the same as or different from each other, and each independently a methyl group; Or a phenyl group unsubstituted or substituted with tert-butyl group.

According to an exemplary embodiment of the present specification, Rc is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another exemplary embodiment, Rc is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another exemplary embodiment, Rc is 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.

According to another exemplary embodiment, Rc is a substituted or unsubstituted aryl group.

In another exemplary embodiment, Rc is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another exemplary embodiment, Rc is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Rc is a halogen group, deuterium, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted.

According to another exemplary embodiment, Rc is a phenyl group unsubstituted or substituted with 1 or more selected from the group consisting of a halogen group, deuterium, an alkyl group having 1 to 20 carbon atoms, and a silyl group; A biphenyl group unsubstituted or substituted with one or more selected from the group consisting of a halogen group, deuterium, an alkyl group having 1 to 20 carbon atoms and a silyl group; A terphenyl group unsubstituted or substituted with one or more selected from the group consisting of a halogen group, deuterium, an alkyl group having 1 to 20 carbon atoms and a silyl group; A fluorenyl group unsubstituted or substituted with one or more selected from the group consisting of a halogen group, deuterium, an alkyl group having 1 to 20 carbon atoms and a silyl group; Or a naphthyl group unsubstituted or substituted with one or more selected from the group consisting of a halogen group, deuterium, an alkyl group having 1 to 20 carbon atoms and a silyl group.

In another embodiment, Rc is a phenyl group unsubstituted or substituted with one or more selected from the group consisting of a halogen group, deuterium, methyl group, tert-butyl group and trimethylsilyl group; A biphenyl group unsubstituted or substituted with one or more selected from the group consisting of a halogen group, deuterium, methyl group, tert-butyl group and trimethylsilyl group; A terphenyl group unsubstituted or substituted with one or more selected from the group consisting of a halogen group, deuterium, methyl group, tert-butyl group and trimethylsilyl group; A fluorenyl group unsubstituted or substituted with one or more selected from the group consisting of a halogen group, deuterium, methyl group, tert-butyl group and trimethylsilyl group; Or a naphthyl group unsubstituted or substituted with one or more selected from the group consisting of a halogen group, deuterium, methyl group, tert-butyl group and trimethylsilyl group.

According to another exemplary embodiment, Rc is a phenyl group; tert-butylphenyl group; Fluorophenyl group; Trimethylsilylphenyl group; Dimethylphenyl group; A phenyl group substituted with deuterium; Biphenyl group; Terphenyl group; 9,9-dimethylfluorenyl group; Or a naphthyl group.

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

According to another exemplary embodiment, Rd and Re are the same as or different from each other, and each independently substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another exemplary embodiment, Rd and Re are the same as or different from each other, and each independently substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Rd and Re are the same as or different from each other, and each independently an alkyl group having 1 to 20 carbon atoms; Or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

In another exemplary embodiment, Rd and Re are the same as or different from each other, and each independently a methyl group; Or a phenyl group unsubstituted or substituted with tert-butyl group.

In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Compounds 1 to 60.

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

For example, the compound of Formula 1 may have a core structure as shown in the following scheme. Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be varied according to techniques known in the art. In addition, when other types of intermediates are used, compounds having different structures corresponding to Formula 1 may be obtained.

<Reaction formula>

-Reaction Scheme for Making Compound A Type

Intermediate-1 can be used to synthesize intermediate-2 through oxidative C-H amination using Pd.

As described below, various Ar groups were introduced from the intermediate (intermediate-3, 4) obtained through a bromination reaction and a protecting group removal reaction to a general Suzuki reaction, and then, a Buckwald amination reaction was used. By introducing various Ar ₃ , various kinds of products can be synthesized.

-Reaction scheme for making compound B type

Intermediate-5 obtained intermediate-6 by dimerization reaction using Pd, and then intermediate-7 was produced through a bromination reaction, and between this compound and boronic acid or borate compound (boronic acid or borate compound) having various substituents (R) Compound B (product B) having various substituents can be synthesized using a general Suzuki reaction.

In addition, by introducing various substituents to the core structure of the structure as described above, it is possible to synthesize a compound having intrinsic properties of the introduced substituents. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, a light emitting layer material, and an electron transport layer material used in manufacturing an organic light emitting device into the core structure, a material satisfying the conditions required for each organic material layer can be synthesized. 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 layer of the organic material layer includes a compound represented by Chemical Formula 1.

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

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 application method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited to this, and may include more or fewer 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 electron injection layer may include a compound represented by Chemical Formula 1.

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 Chemical Formula 1.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.

According to another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1 as a dopant in the light emitting layer.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 as a dopant in the light emitting layer, and includes a fluorescent host or a phosphorescent host, and other organic compounds, metals or metal compounds It may include as a dopant.

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

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

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

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

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

In one 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 the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. 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 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 metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to have a metal or conductive metal oxide on the substrate or alloys thereof To form an anode, and to form 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. Can. In addition to this method, an organic light emitting device may be made by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into an organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There is a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole-injecting material is a material that can be easily injected holes from the anode at a low voltage, and it is preferable that the high-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 material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

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

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

The host material of the light emitting layer includes a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

The iridium-based 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 transport material, a material capable of receiving electrons from the cathode well and transferring them to the light emitting layer, a material having high mobility for electrons is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including 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 for the light emitting layer or the light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, Also, a compound having excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

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

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

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

Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present application is not interpreted to be limited to the embodiments described below. The embodiments of the present application are provided to more fully describe the present specification to those skilled in the art.

< Manufacturing example >

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

A-1-1 (50 g), bis(pinacolato)diboron (47 g), KOAc (27.2 g) tricyclohexylphosphine (0.97 g) Pd (dba ) The flask containing ₂ (1.0 g) and 1,4-dioxane [1,4-dioxane] (600 ml) was heated at 110° C. and stirred for 5 hours. The reaction solution was cooled to room temperature, separated by adding water and aq.NaCl, and filtered by treatment 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 (42.8 g).

A-1-2 (40 g), bis(triphenylphosphine)palladium (1.78 g), potassium phosphate (74 g) and 1,4-dioxane [1,4 -dioxane] (900 ml) and a flask containing distilled water (300 mL) was 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, and filtered by treatment with MgSO ₄ (anhydrous). The filtered solution was distilled off under reduced pressure and purified by silica gel column chromatography (developer: hexane/ethyl acetate = 30/1 (volume ratio)) to obtain intermediate A-1-3 (15.7 g). As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=365.

Manufacturing example 2. [Intermediate A-1- 5] of synthesis

After A-1-3 (15 g) was dissolved in chloroform (200 mL), boron tribromide (11.9 mL) was slowly added dropwise at 0° C., and then stirred 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 treatment with MgSO ₄ (anhydrous). The filtered solution was distilled off under reduced pressure and dissolved in dimethylformamide [DMF] (200 mL), followed by perfluorobutanesulfonyl floride (31 g) and potassium carbonate (17 g). Put in, and stirred at room temperature for 12 hours. Distilled water (500 mL) was added, the mixture was 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 A-1-4 (19.5 g).

Intermediate A-1-4 (19 g), p-toluenesulfonamide (4 g), tris(dibenzylideneacetone)dipalladium(0)[tris(dibenzylideneacetone)dipalladium(0)] (0.39 g), a flask containing tBuXPhos (0.36 g), K ₃ PO ₄ (11.2 g) and 1,4-dioxane [1,4-dioxane] (150 ml) was 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, and filtered by treatment with MgSO ₄ (anhydrous). The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain intermediate A-1-5 (15.0 g). As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=643.

Manufacturing example 3. [Intermediate A-1- 7] of synthesis

Intermediate A-1-5 (13 g), palladium(II) aceated[[Palladium(II) aceated](0.45 g), potassium peroxymonosulfate[oxone](6.2 g), p-toluenesulphonic acid mono The flask containing hydrate [p-toluenesulfonic acid monohydrate] (1.9 g) and pavalic acid (50 ml) and DMF (150 mL) was heated at 40° C. and stirred for 12 hours. The reaction solution was cooled to room temperature, neutralized by adding water and aq.NaHCO ₃ , and then the solid was filtered. The filtered solid was purified by recrystallization (ethyl acetate/hexane), and intermediate A-1-6 (6.6 g) Got

The flask containing intermediate A-1-6 (6 g) and N-bromosuccinimide [NBS] (7.5 g) and chloroform (50 mL) was stirred at room temperature for 5 hours. 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 treatment with MgSO ₄ (anhydrous). The filtered solution was distilled off under reduced pressure and purified by recrystallization (Chlorform/hexane) to obtain intermediate A-1-7 (5.7 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=951.

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

Intermediate A-1-7 (4 g) was dissolved in dimethyl sulfoxide [DMSO] (30 mL), and then potassium hydroxide (2.4 g) and ethanol (10 mL) were added. After stirring at room temperature for 4 hours, 100 mL of distilled water was slowly added dropwise and stirred for 30 minutes. The resulting solid was filtered under reduced pressure, and the filtered solid was purified by recrystallization (toluene/hexane). The obtained solid and tetrakis(triphenyl-phosphine)palladium(0)[tetrakis(triphenyl-phosphine)palladium(0)](0.24g), K ₂ CO ₃ (3.5g), 2-methylphenyl boronic acid The flask containing [2-methylphenylboronic acid] (2.5 g) and 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, separated by adding water and aq.NH ₄ Cl, and filtered by treatment with MgSO ₄ (anhydrous). The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain intermediate A-1-8 (2.2 g).

Intermediate A-1-8 (2.2 g), bis(triphenylphosphine)palladium(0)[bis(triphenylphosphine)palladium(0)](33mg), sodium tert-butoxide(1.2g ), p-fluorophenylbromide (p-fluorophenylbromide) (1.2 g) and toluene (30 ml) containing the flask was heated at 120 ℃, and stirred for 12 hours. The reaction solution was cooled to room temperature, separated by adding water and aq.NH ₄ Cl, and filtered by treatment with MgSO ₄ (anhydrous). 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 (1.9 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+] = 879.

Manufacturing example 5. [Intermediate A-2- 2] of synthesis

Intermediate A-1-6 (5 g) was dissolved in DMSO (50 mL), followed by addition of potassium hydroxide (4.4 g) and ethanol (15 mL). After stirring at room temperature for 4 hours, 100 mL of distilled water was slowly added dropwise and stirred for 30 minutes. The resulting solid was filtered under reduced pressure, and the filtered solid was dissolved in toluene (100 mL), neutralized with aq.NH ₄ Cl, and then the organic layer was separated and filtered by MgSO ₄ (anhydrous) treatment. The filtered solution was distilled off under reduced pressure and dissolved in DMF (80 mL). NBS (11.8 g) and trifluoroacetic acid (0.15 mL) were added, followed by stirring at room temperature for 2 hours. Aq.Na ₂ S ₂ O ₃ and aq. NaHCO ₃ 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-2-1 (3.2 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=954.

Intermediate A-2-1 (3.2 g), tetrakis(triphenylphosphine)palladium(0)] (40 mg), K ₂ CO ₃ (2.3 g), 4-tert The flask containing -butylphenylboronic acid (2.5 g) and 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, separated by adding water and aq.NH ₄ Cl, and filtered by treatment with MgSO ₄ (anhydrous). The filtered solution was distilled off under reduced pressure, then dissolved in THF (30 mL, anhydrous) and cooled to -78 °C. N-butyllithium [5.3 mL, 2.5M in hexane) was slowly added dropwise and stirred at -78°C for 2 hours and at 0°C for 30 minutes. After adding aq.NH ₄ Cl at 0°C and separating, MgSO ₄ (anhydrous) treatment was performed. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain compound A-2-2 (1.7 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=859.

Manufacturing example 6. [Compound A- 2] of synthesis

Compound A-2 (1.5 g) can be obtained similarly to the preparation method of compound A-1 of Preparation Example 4 using intermediate A-2-2 (1.6 g). As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+] = 1111.

Manufacturing example 7. [Intermediate B-1- 3] of synthesis

Flask containing intermediate B-1-1 (70 g), potassium carbonate (66 g), perfluorobutanesulfonyl floride (126 g) and DMF (1 L) at room temperature 2 Stir for hours. Distilled water (500 mL) was added, the mixture was 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-1-2 (133 g).

Using intermediate B-1-2 (120 g), intermediate B-1-3 (54 g) can be obtained in the same manner as the method for synthesizing intermediate A-1-2 of Preparation Example 1. As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=329.

Manufacturing example 8. [Intermediate B-1- 5] of synthesis

Intermediate B-1-4 (16.7 g) can be obtained in the same manner as the method for synthesizing intermediate A-1-3 of Preparation Example 1 using intermediate B-1-3 (50 g).

To a flask containing intermediate B-1-4 (16 g), acetic acid (50 mL) and DMF (250 mL), bromine (31.5 g) was slowly added dropwise 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 B-1-5 (19.6 g). As a result of measuring the mass spectrum of the obtained solid, the peak at [M+H+]=645 Was confirmed.

Manufacturing example 9. [Compound B- 1] of synthesis

Compound B-1 (3.9 g) can be obtained in the same manner as the method for synthesizing intermediate A-1-8 of Preparation Example 4 using Intermediate B-1-5 (5 g). As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=941.

Manufacturing example 10. [Compound B- 2] of synthesis

Compound B-2 (2.3 g) can be obtained similarly to the method for synthesizing Compound A-2 of Preparation Example 6 using Intermediate B-1-5 (5 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=1225.

Manufacturing example 11. [Intermediate A-3- 2] of synthesis

Intermediate A-1-7 (8 g) was dissolved in DMSO (60 mL), and then potassium hydroxide (5 g) and ethanol (20 mL) were added. After stirring at room temperature for 4 hours, 150 mL of distilled water was slowly added dropwise and stirred for 30 minutes. The resulting solid was filtered under reduced pressure, and the filtered solid was purified by recrystallization (ethyl acetate/hexane) to obtain intermediate A-3-1 (3.85 g).

140 flask containing intermediate A-3-1 (3.8 g), 4-cyanofluorobenzene [2.85 g], Cs ₂ CO ₃ (5.7 g) and xylene (40 mL) Heated at °C and stirred for 6 hours. The reaction solution was cooled to room temperature, separated by adding water and aq.NH ₄ Cl, and filtered by treatment with MgSO ₄ (anhydrous). The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain intermediate A-3-2 (3.3 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=831.

Manufacturing example 11. [Compound A- 3] of synthesis

- THF was cooled to-78 ℃ (35 mL, anhydrous) Intermediate A-3-2 (3g) n- butyllithium [n-butyllithium] (6.3mL, 2.5M in hexane) to a flask containing the dissolved in a slowly added dropwise It was then stirred for 2 hours at the same temperature. Subsequently, chlorotrimethylsilane (2.7 mL, anhydrous) was added, and then the temperature was gradually raised to room temperature and stirred at room temperature for 12 hours. Water and aq.NH ₄ Cl were added for separation, followed by MgSO ₄ (anhydrous) treatment. The filtered solution was distilled off under reduced pressure and purified by silica gel column chromatography (developing solution: hexane/toluene = 15/1 (volume ratio)) to obtain compound A-3 (1 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=807.

< Example >

Example One.

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was put in distilled water in which a dispersing agent was dissolved and washed with ultrasonic waves. As a detergent, a product of Fischer Co. was used, and distilled water was used by Millipore Co. Distilled water, which was second filtered as a product filter, was used. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the prepared ITO transparent electrode, the compound HAT was thermally vacuum-deposited to a thickness of 50 Pa to form a hole injection layer. Then, the following compound HT-A 1000 진공 was vacuum-deposited as a hole transport layer, and subsequently the compound HT-B 100Å was deposited. On the light emitting layer, BH-A as a host and A-1 as a dopant were vacuum deposited to a thickness of 200 mm 2 at 2% by weight.

Subsequently, 300 화합물 of the following compound ET-A and the compound Liq were deposited at a 1:1 ratio, and sequentially, 150 Å thick silver (Ag) 10% by weight doped magnesium (Mg) and 1,000 Å thick aluminum were deposited. 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, LiF was 0.2 Å/sec, and aluminum was maintained at a deposition rate of 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 A-2 was used instead of Compound A-1.

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-1.

Comparative example One.

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-1.

Comparative example 2.

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

The driving voltage and efficiency of the organic light emitting devices manufactured in Examples 1 to 3 and Comparative Examples 1 and ² were measured at a current density of 10 mA/cm ² , and compared to an initial luminance at a current density of 20 mA/cm ² . The time to 90% (life) was measured. The results are shown in Table 1 below.

Experimental Example Dopant 10mA/cm ² 20mA/cm ² Driving voltage (V) Efficiency (cd/A) Life (hr) Example 1 A-1 5.8 4.5 198 Example 2 A-2 5.8 3.9 210 Example 3 B-2 5.5 6.1 200 Comparative Example 1 C-1 5.9 2.8 160 Comparative Example 2 C-2 6.1 1.7 22

From the results of Table 1, Examples 1 to 3 than Comparative Example 1 using a compound in which a substituent is not bonded to the benzene ring of the core and Comparative Example 2 using a compound in which the benzene ring of the core forms a condensed ring by bonding to each other It can be seen that the driving voltage, efficiency and life characteristics of the device are excellent.

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

Claims (8)

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

[Formula 3]

In Chemical Formulas 2 and 3,
X1 and X2 are the same as or different from each other, and each independently O, S, CRaRb, NRc or SiRdRe,
Ra, Rb, Rc, Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar1 and Ar4 are the same as each other, and a cyano group; Boron group; Silyl 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,
Ar2 and Ar3 are the same as each other, and a cyano group; Boron group; Silyl 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,
Ar5 and Ar6 are the same as each other, and a cyano group; Boron group; Silyl 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 Compound represented by any one of the following compounds 1 to 60:

. A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises a compound according to any one of claims 1 and 4. Light emitting element. The method according to claim 5,
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 according to claim 5,
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 according to claim 5,
The organic material layer includes an emission layer, and the emission layer includes the compound.

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