KR102256782B1 - Multicyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

A polycyclic compound and an organic light-emitting device including the same TECHNICAL FIELD [0002]

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

In the present specification, an organic light-emitting device is a light-emitting device using an organic semiconductor material, and requires an exchange of holes and/or electrons between an electrode and an organic semiconductor material. Organic light emitting devices can be divided into two types as follows according to the principle of operation. First, excitons are formed in the organic material layer by photons introduced into the device from an external light source, and these excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes, and used as a current source (voltage source). It is a type of light emitting device. The second is a light emitting device in which holes and/or electrons are injected into an organic semiconductor material layer forming an interface with the electrode by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows. These organic light emitting devices are known to have 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 can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions. Light-emitting materials include blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary to realize better natural colors according to the light-emitting color.

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

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

Korean Patent Laid-Open Publication No. 10-2009-0064540

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

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

[Formula 1]

In Formula 1,

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

Y is O, S or CRdRe,

Ra, Rb, Rc, Rd, Re, and R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a to c are each an integer of 0 to 4,

When a to c are each an integer of 2 or more, the substituents in parentheses are the same as or different from each other.

In addition, according to an exemplary embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

The compounds described herein can be used as a material for an organic material layer of an organic light-emitting device. When manufacturing an organic light-emitting device containing the compound according to at least one embodiment, an organic light-emitting device having high efficiency and long life can be obtained, and when the compound of the present invention is included in the light-emitting layer of the organic light-emitting device, high color gamut It is possible to manufacture an organic light emitting device having.

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.
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 I did it.
3 shows a graph of LC-Mass measurement of Compound 10.

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

The present specification provides a compound represented by the following formula (1). When the compound represented by the following formula (1) is used in the organic material layer of the organic light-emitting device, the efficiency and lifespan characteristics of the organic light-emitting device are always maintained.

Also. The compound according to an exemplary embodiment of the present application minimizes the separation of HOMO and LUMO and moves very efficiently in the movement of electrons and majors to form excitons, thereby maximizing luminescence characteristics. When a blue organic light-emitting device is manufactured using this, it can have a high color reproducibility in not only upper light emission but also lower light emission.

Also. The compound according to the exemplary embodiment of the present application may have a high color gamut with a structure having a narrow half width.

[Formula 1]

In Formula 1,

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

Y is O, S or CRdRe,

Ra, Rb, Rc, Rd, Re, and R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a to c are each an integer of 0 to 4,

When a to c are each an integer of 2 or more, the substituents in parentheses are the same as or different from each other.

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

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

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

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

In the present specification, the term "substituted or unsubstituted" refers to deuterium; 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 amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent to which two phenyl groups are connected.

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

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

In the present specification, the silyl group may be represented by the formula of _{-SiY a} Y _b Y _{c , wherein Y a} , Y _b and Y _c 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, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto. Does not.

In the present specification, the boron group may be represented by the formula of _{-BY d} Y _{e , wherein Y d} and Y _e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.

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 an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and the like.

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

In the present specification, the amine group is -NH ₂ ; Alkylamine group; Arylalkylamine group; Arylamine group; Arylheteroarylamine group; It may be selected from the group consisting of an alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60.

In the present specification, the number of carbon atoms in the alkylamine group is not particularly limited, but may be 1 to 40, and according to an embodiment, may be 1 to 20. Specific examples of the alkylamine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group.

In the specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a biphenylphenylamine group, a dibiphenylamine group, and fluorine. Nilphenylamine group, and the like, but are not limited thereto.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.

In the present specification, an arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group.

In the present specification, an arylalkylamine group means an aryl group and an amine group substituted with an alkyl group.

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

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

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

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

,

Spirofluorenyl groups such as,

(9,9-dimethylfluorenyl group), and

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

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si, and Se as hetero atoms, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group. And the like, but are not limited to these.

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

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

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

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

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or an aryl group except for the divalent group.

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

In the present specification, the heterocycle is an atom other than carbon and contains one or more heteroatoms, and specifically, the heteroatoms include one or more atoms selected from the group consisting of N, O, P, S, Si, and Se, etc. can do. The heterocycle may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group, except that it is a divalent group.

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

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.

In the exemplary embodiment of the present specification, Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C60 alkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

According to another exemplary embodiment, the Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

In another exemplary embodiment, Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted 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 substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted pentyl group; Or a substituted or unsubstituted hexyl group.

In another exemplary embodiment, Ra and Rb are the same as or different from each other, and each independently a methyl group; Ethyl group; Propyl group; Butyl group; Pentyl group; Or a hexyl group.

According to an exemplary embodiment of the present specification, Rc is a substituted or unsubstituted alkyl group having 1 to 60 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 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Rc is a substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

According to an exemplary embodiment of the present specification, Y is O, S, or CRdRe.

According to an exemplary embodiment of the present specification, Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, the Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In another exemplary embodiment, Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted pentyl group; A substituted or unsubstituted hexyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted biphenyl group.

According to another exemplary embodiment, the Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; Propyl group; Butyl group; Pentyl group; Hexyl group; Phenyl group; Biphenyl group; Or a naphthyl group.

According to another exemplary embodiment, Rd and Re are a methyl group, an ethyl group, or a phenyl group.

According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

According to another exemplary embodiment, R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In another exemplary embodiment, R1 is hydrogen; heavy hydrogen; Cyano group; Silyl group; Boron group; Or a substituted or unsubstituted C 1 to C 20 alkyl group.

According to another exemplary embodiment, R1 is hydrogen; heavy hydrogen; Cyano group; Silyl group; Boron group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted pentyl group; Or a substituted or unsubstituted hexyl group.

In another exemplary embodiment, R1 is hydrogen; heavy hydrogen; Cyano group; Silyl group; Boron group; Methyl group; Ethyl group; Propyl group; Isopropyl group; Butyl group; Pentyl group; Or a hexyl group.

According to an exemplary embodiment of the present specification, a is an integer of 0 to 2, and when a is 2, two R1s are the same as or different from each other.

According to an exemplary embodiment of the present specification, R4 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted C1-C60 alkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

According to another exemplary embodiment, the R4 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

In another exemplary embodiment, R4 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C 1 to C 20 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, the R4 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted pentyl group; A substituted or unsubstituted hexyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted naphthyl group.

According to another exemplary embodiment, R4 and R5 are the same as or different from each other, and each independently hydrogen or deuterium.

According to an exemplary embodiment of the present specification, b and c are each an integer of 1 to 4, when b is 2 or more, 2 or more R2s are the same as or different from each other, and when c is 2 or more, 2 or more R3s are the same or different from each other. Do.

According to another exemplary embodiment, b and c are 1 or 2, respectively.

According to an exemplary embodiment of the present specification, R2 and R3 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 aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group.

In another exemplary embodiment, R2 and R3 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 aryl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heterocyclic group. The aryl group may have 6 to 60 carbon atoms, the heteroaryl group may have 2 to 60 carbon atoms, and the alkyl group may have 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by Chemical Formula 2 below.

[Formula 2]

In Formula 2,

X1, X2, Y, R1, R4, R5 and a are as defined in Formula 1,

R21 and R31 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or heteroaryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

b1 and c1 are each an integer of 0 to 4, and when b1 and c1 are each 2 or more, the substituents in parentheses are the same as or different from each other,

m1 and m2 are each 0 or 1, m1+b1 is an integer of 0-4, and m2+c1 is an integer of 0-4.

According to an exemplary embodiment of the present specification, R21 and R31 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted C1-C60 alkyl group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

According to another exemplary embodiment, R21 and R31 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

In another exemplary embodiment, R21 and R31 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Or a substituted or unsubstituted C 1 to C 20 alkyl group.

According to another exemplary embodiment, R21 and R31 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; Or a substituted or unsubstituted butyl group.

According to another exemplary embodiment, R21 and R31 are the same as or different from each other, and each independently hydrogen; Methyl group; Or isopropyl group.

According to an exemplary embodiment of the present specification, b1 and c1 are each an integer of 0 to 4, when b1 is 2 or more, two or more R21s are the same as or different from each other, and when c1 is 2 or more, two or more R31s are the same or different from each other. Do.

According to another exemplary embodiment, b1 and c1 are 0 or 1, respectively.

According to the exemplary embodiment of the present specification, m1 and m2 are each 0 or 1, m1+b1 is an integer of 0 to 4, and m2+c1 is an integer of 0 to 4.

According to another exemplary embodiment, m1 and m2 are 1, and b1 and c1 are integers of 0 to 3, respectively.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group.

In another exemplary embodiment, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted C6 to C30 arylene group.

According to another exemplary embodiment, the L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

In another exemplary embodiment, L1 and L2 are direct bonds.

In another exemplary embodiment, L1 and L2 are the same as or different from each other, and each independently a phenylene group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

In another exemplary embodiment, L1 and L2 are the same as or different from each other, and each independently a phenylene group unsubstituted or substituted with a methyl group.

According to another exemplary embodiment, the L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a dimethylphenylene group.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently 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, or adjacent groups are bonded to each other to form a substituted or unsubstituted heterocycle.

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently 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, or adjacent groups are bonded to each other to form a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently a cyano group, a silyl group, or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; Or a cyano group, a silyl group, or a C2-C30 heteroaryl group unsubstituted or substituted with a C1-C10 alkyl group, or adjacent groups are bonded to each other and substituted or furnished with a cyano group, a silyl group, or a C1-C10 alkyl group It forms a cyclic C2-C30 heterocycle.

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted triazine group, or adjacent groups are bonded to each other to form a substituted or unsubstituted carbazole.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently a cyano group, a silyl group, or a phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; A biphenyl group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; A terphenyl group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; A naphthyl group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; A dibenzofuran group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; A dibenzothiophene group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; A fluorenyl group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; A pyridine group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; A pyrimidine group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; Or a cyano group, a silyl group, or a triazine group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, or adjacent groups are bonded to each other to form a carbazole substituted or unsubstituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms do.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a cyano group, a methyl group, a trimethylsilyl group, or a phenyl group unsubstituted or substituted with a tert-butyl group; A biphenyl group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; A terphenyl group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; A naphthyl group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; A dibenzofuran group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; A dibenzothiophene group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; A fluorenyl group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; A pyridine group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; A pyrimidine group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; Or a cyano group, a methyl group, a trimethylsilyl group, or a triazine group unsubstituted with a tert-butyl group, or adjacent groups are bonded to each other to form a carbazole substituted or unsubstituted with a cyano group, methyl group, trimethylsilyl group or tert-butyl group do.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a cyano group, a methyl group, a trimethylsilyl group, or a phenyl group unsubstituted or substituted with a tert-butyl group; Biphenyl group; A fluorenyl group substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group; Dibenzothiophene group; Or a cyano group or a pyridine group unsubstituted or substituted with a methyl group, or adjacent groups are bonded to each other to form a carbazole. Ar1 and Ar2 may be adjacent groups, and Ar3 and Ar4 may be adjacent groups.

According to an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by Chemical Formula 3 or 4 below.

[Formula 3]

[Formula 4]

In Formulas 3 and 4,

X1, X2, Y, R1, R4, R5 and a are as defined in Formula 1,

R6, R7, R21 and R31 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar21 to Ar24 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

b11 and c11 are each an integer of 0 to 3, and when b11 and c11 are each 2 or more, the substituents in parentheses are the same as or different from each other,

e and f are each an integer of 0 to 8, and when e and f are each 2 or more, the substituents in parentheses are the same as or different from each other.

In Formulas 3 and 4, R21, R31, L1, L2, R1, R4, R5, X1, X2 and a are as described above.

According to an exemplary embodiment of the present specification, b11 and c11 are 0 or 1, respectively.

According to an exemplary embodiment of the present specification, R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted C1-C60 alkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

According to another exemplary embodiment, R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

In another exemplary embodiment, R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group (-CN); Or a substituted or unsubstituted C 1 to C 20 alkyl group.

According to another exemplary embodiment, R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group (-CN); A substituted or unsubstituted methyl group; Or a substituted or unsubstituted tert-butyl group.

According to an exemplary embodiment of the present specification, e and f are integers of 0 to 8, when e is 2 or more, 2 or more R6 are the same as or different from each other, and when f is 2 or more, 2 or more R7 are the same or different from each other. .

In another exemplary embodiment, e and f are 0 or 1.

According to an exemplary embodiment of the present specification, Ar21 to Ar24 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

According to another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and each independently a cyano group, a silyl group, or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; Or it is a C2-C30 heteroaryl group substituted or unsubstituted with a cyano group, a silyl group, or a C1-C10 alkyl group.

According to another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted triazine group.

In another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and each independently a cyano group, a silyl group, or a phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; A biphenyl group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; A terphenyl group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; A naphthyl group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; A dibenzofuran group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; A dibenzothiophene group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; A fluorenyl group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; A pyridine group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; A pyrimidine group unsubstituted or substituted with a cyano group, a silyl group, or an alkyl group having 1 to 10 carbon atoms; Or a cyano group, a silyl group, or a triazine group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Ar21 to Ar24 are the same as or different from each other, and each independently a cyano group, a methyl group, a trimethylsilyl group, or a phenyl group unsubstituted or substituted with a tert-butyl group; A biphenyl group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; A terphenyl group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; A naphthyl group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; A dibenzofuran group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; A dibenzothiophene group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; A fluorenyl group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; A pyridine group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; A pyrimidine group unsubstituted or substituted with a cyano group, a methyl group, a trimethylsilyl group, or a tert-butyl group; Or a cyano group, a methyl group, a trimethylsilyl group, or a triazine group unsubstituted or substituted with a tert-butyl group.

According to an exemplary embodiment of the present specification, Ar21 to Ar24 are the same as or different from each other, and each independently a cyano group, a methyl group, a trimethylsilyl group, or a phenyl group unsubstituted or substituted with a tert-butyl group; Biphenyl group; A fluorenyl group substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group; Dibenzothiophene group; Or a cyano group or a pyridine group unsubstituted or substituted with a methyl group.

According to the exemplary embodiment of the present specification, Ar21 to Ar24 are the same as or different from each other, and each may be independently represented by the following Formula 3-1 or 3-2.

[Chemical Formula 3-1]

[Chemical Formula 3-2]

In Formulas 3-1 and 3-2,

X3 is O, S, CRR' or NR",

X4 to X6 are the same as or different from each other, and each independently CRf, or N,

R, R', R", Rf, R8 and R9 are the same as or different from each other, and each independently hydrogen; deuterium; halogen group; cyano group (-CN); silyl group; boron group; substituted or unsubstituted 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 heterocyclic group,

g is an integer from 0 to 7, and when g is 2 or more, R8 is the same as or different from each other,

h is an integer of 0 to 2, and when h is 2, R9 is the same as or different from each other.

According to an exemplary embodiment of the present specification, X3 is O, S, CRR' or NR".

According to another exemplary embodiment, X3 is O, S, or CRR'.

According to an exemplary embodiment of the present specification, R, R'and R" are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In another exemplary embodiment, R, R'and R" are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted methyl group; or a substituted or unsubstituted tert-butyl group.

According to another exemplary embodiment, the R, R'and R" are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted methyl group.

In another exemplary embodiment, R, R'and R" are the same as or different from each other, and each independently hydrogen; or a methyl group.

According to an exemplary embodiment of the present specification, X4 to X6 are the same as or different from each other, and each independently CRf or N.

In another exemplary embodiment, any one of X4 to X6 is N, and the other two are CRf.

In another exemplary embodiment, X4 to X6 are CRf.

In the exemplary embodiment of the present specification, Rf is hydrogen; Cyano group; Silyl group; A substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Rf is hydrogen; Cyano group; Trimethylsilyl group; A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

According to another exemplary embodiment, Rf is a cyano group, a methyl group, a trimethylsilyl group, a tert-butyl group, or a phenyl group.

According to an exemplary embodiment of the present specification, R8 and R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another exemplary embodiment, R8 and R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl group; A substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another exemplary embodiment, R8 and R9 are the same as or different from each other, and each independently hydrogen; Cyano group (-CN); Silyl group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted biphenyl group.

According to another exemplary embodiment, R8 and R9 are the same as or different from each other, and each independently hydrogen; Cyano group (-CN); Trimethylsilyl group; Methyl group; tert-butyl group; Or a phenyl group.

According to an exemplary embodiment of the present specification, g and h are 0 or 1, respectively.

In the exemplary embodiment of the present specification, Formula 1 may be represented by any one of the following structures.

The compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by a method described below. Substituents may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

The conjugation length and energy bandgap of a compound are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy band gap.

In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents to the core structure of Formula 1. In addition, in the present invention, the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure of Formula 1.

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

In addition, the organic light emitting device according to the present invention includes a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the above-described compound.

According to an exemplary embodiment of the present specification, the organic material layer may include an emission layer, and the emission layer may include a compound represented by Formula 1A below.

Among the organic material layers of the organic light emitting device of the present specification, the structure of Formula 1A may be included as a material for the host of the light emitting layer.

[Formula 1A]

In Formula 1A,

L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R24 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

p is an integer from 0 to 6,

When p is 2 or more, the substituents in parentheses are the same as or different from each other.

In the exemplary embodiment of the present specification, L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroarylene group.

In the exemplary embodiment of the present specification, L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted C2 to C40 heteroarylene group.

According to another exemplary embodiment, the L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophenylene group; A substituted or unsubstituted furanylene group; A substituted or unsubstituted dibenzothiophenylene group; A substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted carbazolylene group.

In another exemplary embodiment, L103 to L106 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Terphenylene group; Naphthylene group; Anthracenylene group; Phenanthrenylene group; Triphenylene group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Thiophenylene group; Furanylene group; Dibenzothiophenylene group; Dibenzofuranylene group; Or a carbazolylene group unsubstituted or substituted with an ethyl group or a phenyl group.

According to another exemplary embodiment, the L103 to L106 are the same as or different from each other, and each independently a direct bond; Or it may be selected from the following structures.

According to an exemplary embodiment of the present specification, L103 is a direct bond.

According to an exemplary embodiment of the present specification, L104 is a phenylene group.

According to an exemplary embodiment of the present specification, L105 and L106 are direct bonds.

In the exemplary embodiment of the present specification, R24 is hydrogen; heavy hydrogen; Halogen group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, R24 is 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 heterocyclic group.

In the exemplary embodiment of the present specification, R24 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C50 alkyl group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C40 heterocyclic group.

In the exemplary embodiment of the present specification, R24 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C25 heterocyclic group.

In another exemplary embodiment, R24 is hydrogen.

According to an exemplary embodiment of the present specification, p is 0 or 1.

In the exemplary embodiment of the present specification, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

According to another exemplary embodiment, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; A C6-C60 aryl group unsubstituted or substituted with a C6-C60 aryl group or a C2-C60 heteroaryl group; Or a C2-C60 heteroaryl group substituted or unsubstituted with a C2-C60 aryl group or a C2-C60 heteroaryl group.

In another exemplary embodiment, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted indolecarbazole group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted isoquinolyl group; A substituted or unsubstituted quinolyl group; A substituted or unsubstituted quinazolyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; A substituted or unsubstituted xanthene group; Or a substituted or unsubstituted dibenzosilol group.

According to another exemplary embodiment, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; Phenanthrene group; Anthracene group; Triphenylene group; A dibenzofuran group unsubstituted or substituted with an aryl group; Naphthobenzofuran group; A dibenzothiophene group unsubstituted or substituted with an aryl group; A carbazole group unsubstituted or substituted with an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; Thiophene group unsubstituted or substituted with an aryl group; A furan group unsubstituted or substituted with an aryl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with an alkyl group or an aryl group; Benzofluorene group unsubstituted or substituted with an alkyl group or an aryl group; Indolecarbazole; Pyridyl group; An isoquinolyl group unsubstituted or substituted with an aryl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with an aryl group; A triazine group unsubstituted or substituted with an aryl group; A benzimidazole group unsubstituted or substituted with an aryl group; Benzoxazole group unsubstituted or substituted with an aryl group; Benzothiazole group unsubstituted or substituted with an aryl group; Dihydroacridine group unsubstituted or substituted with an alkyl group or an aryl group; A xanthene group unsubstituted or substituted with an alkyl group or an aryl group; Or a dibenzosilol group unsubstituted or substituted with an alkyl group or an aryl group.

In another exemplary embodiment, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrene group; Anthracene group; Triphenylene group; A dibenzofuran group unsubstituted or substituted with a phenyl group; Naphthobenzofuran group; A dibenzothiophene group unsubstituted or substituted with a phenyl group; A carbazole group unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; A thiophene group unsubstituted or substituted with a phenyl group; A furan group unsubstituted or substituted with a phenyl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with a methyl group or a phenyl group; A benzofluorene group unsubstituted or substituted with a methyl group or a phenyl group; Indolecarbazole; A pyridyl group unsubstituted or substituted with a phenyl group or a naphthyl group; An isoquinolyl group unsubstituted or substituted with a phenyl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with a phenyl group; A triazine group unsubstituted or substituted with a phenyl group; A benzimidazole group unsubstituted or substituted with a phenyl group; A benzoxazole group unsubstituted or substituted with a phenyl group; A benzothiazole group unsubstituted or substituted with a phenyl group; A dihydroacridine group unsubstituted or substituted with a methyl group or a phenyl group; A xanthene group unsubstituted or substituted with a methyl group or a phenyl group; Or a methyl group or a dibenzosilol group unsubstituted or substituted with a phenyl group.

In the exemplary embodiment of the present specification, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Or it may be selected from the following structures.

According to an exemplary embodiment of the present specification, the organic material layer may include an emission layer, at least one of the organic material layers may include the aforementioned compound, and the emission layer may include a compound represented by Formula 1A below.

The organic material layer of the organic light emitting device of the present specification includes an emission layer, and the emission layer may include a compound represented by Formula 1B below. In addition, the compound represented by Formula 1B may be included as a material for a host of the light emitting layer.

[Formula 1B]

In Formula 1B,

L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R25 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

q is an integer from 0 to 7,

When q is 2 or more, the substituents in parentheses are the same as or different from each other.

In the exemplary embodiment of the present specification, R25 is hydrogen; heavy hydrogen; Halogen group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, R25 is 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 heterocyclic group.

In the exemplary embodiment of the present specification, R25 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C50 alkyl group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C40 heterocyclic group.

In the exemplary embodiment of the present specification, R25 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C25 heterocyclic group.

In another exemplary embodiment, R25 is hydrogen.

According to an exemplary embodiment of the present specification, q is 0 or 1.

In the exemplary embodiment of the present specification, L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroarylene group.

In the exemplary embodiment of the present specification, L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted C2 to C40 heteroarylene group.

According to another exemplary embodiment, the L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophenylene group; A substituted or unsubstituted furanylene group; A substituted or unsubstituted dibenzothiophenylene group; A substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted carbazolylene group.

In another exemplary embodiment, L107 to L109 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Terphenylene group; Naphthylene group; Anthracenylene group; Phenanthrenylene group; Triphenylene group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Thiophenylene group; Furanylene group; Dibenzothiophenylene group; Dibenzofuranylene group; Or a carbazolylene group unsubstituted or substituted with an ethyl group or a phenyl group.

According to another exemplary embodiment, the L107 to L109 are the same as or different from each other, and each independently a direct bond; Or it may be selected from the following structures.

In the exemplary embodiment of the present specification, L107 to L109 are direct bonds.

In the exemplary embodiment of the present specification, Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

According to another exemplary embodiment, Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; A C6-C60 aryl group unsubstituted or substituted with a C6-C60 aryl group or a C2-C60 heteroaryl group; Or a C2-C60 heteroaryl group substituted or unsubstituted with a C2-C60 aryl group or a C2-C60 heteroaryl group.

In another exemplary embodiment, Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted indolecarbazole group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted isoquinolyl group; A substituted or unsubstituted quinolyl group; A substituted or unsubstituted quinazolyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; A substituted or unsubstituted xanthene group; Or a substituted or unsubstituted dibenzosilol group.

According to another exemplary embodiment, Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; Phenanthrene group; Anthracene group; Triphenylene group; A dibenzofuran group unsubstituted or substituted with an aryl group; Naphthobenzofuran group; A dibenzothiophene group unsubstituted or substituted with an aryl group; A carbazole group unsubstituted or substituted with an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; Thiophene group unsubstituted or substituted with an aryl group; A furan group unsubstituted or substituted with an aryl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with an alkyl group or an aryl group; Benzofluorene group unsubstituted or substituted with an alkyl group or an aryl group; Indolecarbazole; Pyridyl group; An isoquinolyl group unsubstituted or substituted with an aryl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with an aryl group; A triazine group unsubstituted or substituted with an aryl group; A benzimidazole group unsubstituted or substituted with an aryl group; Benzoxazole group unsubstituted or substituted with an aryl group; Benzothiazole group unsubstituted or substituted with an aryl group; Dihydroacridine group unsubstituted or substituted with an alkyl group or an aryl group; A xanthene group unsubstituted or substituted with an alkyl group or an aryl group; Or a dibenzosilol group unsubstituted or substituted with an alkyl group or an aryl group.

In another exemplary embodiment, Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrene group; Anthracene group; Triphenylene group; A dibenzofuran group unsubstituted or substituted with a phenyl group; Naphthobenzofuran group; A dibenzothiophene group unsubstituted or substituted with a phenyl group; A carbazole group unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; A thiophene group unsubstituted or substituted with a phenyl group; A furan group unsubstituted or substituted with a phenyl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with a methyl group or a phenyl group; A benzofluorene group unsubstituted or substituted with a methyl group or a phenyl group; Indolecarbazole; A pyridyl group unsubstituted or substituted with a phenyl group or a naphthyl group; An isoquinolyl group unsubstituted or substituted with a phenyl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with a phenyl group; A triazine group unsubstituted or substituted with a phenyl group; A benzimidazole group unsubstituted or substituted with a phenyl group; A benzoxazole group unsubstituted or substituted with a phenyl group; A benzothiazole group unsubstituted or substituted with a phenyl group; A dihydroacridine group unsubstituted or substituted with a methyl group or a phenyl group; A xanthene group unsubstituted or substituted with a methyl group or a phenyl group; Or a methyl group or a dibenzosilol group unsubstituted or substituted with a phenyl group.

In the exemplary embodiment of the present specification, Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; Or it may be selected from the following structures.

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

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

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic material layers.

In the organic light-emitting device of the present invention, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the aforementioned compound.

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 the above-described compound.

In another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes the above-described compound.

According to another exemplary embodiment, the organic material layer may include an emission layer, and the emission layer may include the aforementioned compound as a dopant of the emission layer.

In another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes the aforementioned compound as a dopant of the emission layer, includes a fluorescent host or a phosphorescent host, and uses another organic compound, metal, or metal compound as a dopant. Can include.

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

According to an exemplary embodiment of the present invention, the organic material layer includes an emission layer, the emission layer includes the aforementioned compound as a dopant of the emission layer, and the compound of Formula 1A or 1B as a post of the emission layer.

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

As another example, the organic material layer may include an emission layer, and the emission layer may be included as a host of the aforementioned emission layer, and may include a dopant.

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

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

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

1 illustrates a structure of an organic light-emitting device in which an anode 2, 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 emission layer 3.

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

The organic light-emitting device may have, for example, a stacked structure as described below, but is not limited thereto.

(1) Anode/Hole Transport Layer/Light-Emitting Layer/Anode

(2) Anode/Hole Injection Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(3) Anode/Hole Injection Layer/Hole Buffer Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(4) Anode/Hole Transport Layer/Light-Emitting Layer/Electron Transport Layer/Anode

(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode

(7) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode

(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode

(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(10) Anode/hole transport layer/electron suppression layer/light-emitting layer/electron transport layer/cathode

(11) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode

(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light-emitting layer/electron transport layer/cathode

(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light-emitting layer/electron transport layer/electron injection layer/cathode

(14) Anode/Hole Transport Layer/Light-Emitting Layer/Hole Suppression Layer/Electron Transport Layer/Anode

(15) Anode/Hole Transport Layer/Light-Emitting Layer/Hole Suppression Layer/Electron Transport Layer/Electron Injection Layer/Anode

(16) Anode/Hole Injection Layer/Hole Transport Layer/Light-Emitting Layer/Hole Suppression Layer/Electron Transport Layer/Anode

(17) Anode/Hole injection layer/Hole transport layer/Light-emitting layer/Hole suppression layer/Electron transport layer/Electron injection layer/Anode

(18) Anode/Hole injection layer/Hole transport layer/Electron suppression layer/Emitting layer/Hole blocking layer/Electron injection and transport layer/Anode

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

The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and the like, but is not limited thereto and may have a single layer structure. In addition, the organic material layer is made of a variety of polymer materials, and is used in a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made in layers.

The positive electrode is an electrode for injecting holes, and a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer as the positive electrode material. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

The cathode is an electrode for injecting electrons, and it is preferable that the cathode material is a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer, and the hole injection material is a material capable of well injecting holes from the anode at a low voltage. It is preferable that molecular orbital) is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto. The thickness of the hole injection layer may be 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing deterioration of the hole injection characteristics, and when the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There is an advantage that can be prevented.

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

A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.

An electron suppressing layer may be provided between the hole transport layer and the light emitting layer. As the electron suppressing layer, the above-described spiro compound or a material known in the art may be used.

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

Examples of the host material for the light emitting layer include 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, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

When the emission layer emits red light, the emission dopants include PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium). ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a _{fluorescent material such as Alq 3} (tris(8-hydroxyquinolino)aluminum), but is not limited thereto. When the emission layer emits green light, a _{phosphor such as Ir(ppy) 3} (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, it is not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, a _{phosphorescent material such as (4,6-F2ppy) 2} Irpic, spiro-DPVBi, spiro-6P, distillbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.

A hole inhibiting layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.

The electron transport layer may play a role of facilitating transport of electrons. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq _3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing deterioration of the electron transport characteristics, and if the thickness of the electron transport layer is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in driving voltage to improve the movement of electrons. There are advantages to be able to.

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

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

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

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

Hereinafter, in order to describe the present specification in detail, examples will be described in detail. However, the embodiments according to the present specification may 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 more completely describe the present specification to those of ordinary skill in the art.

< Synthesis example >

Synthesis Example 1: Synthesis of Compound 1

One)

[Intermediate 1-1]

Dissolve in 0.47 mol of 3,6-dibromonaphthalene-2,7-diol at room temperature and 800 ml of DMSO (dimethylsulfoxide) in 150 g. In an ice bath, 3.77 mol and 212 g of KOH were slowly added, and then 1.93 mol and 275 g of methyl iodide were added while taking care not to rapidly increase the internal temperature. After the addition was completed, the mixture was raised to room temperature and stirred for an additional 3h. Then, 2.0L of EtOH (ethanol) was added and 2.0L of H ₂ O was sequentially added, followed by stirring for 1 hour. The solid obtained by filtration was washed with 1 L of EtOH, and then dried in an oven to obtain 0.39 mol of the target [Intermediate 1-1] and 135.6 g (yield 83%).

2)

[Intermediate 1-1] [Intermediate 1-2]

At room temperature [Intermediate 1-1] 0.125 mol, 43.4 g and (4-chloro-2-fluorophenyl) boronic acid 0.301 mol, 52.5 g and Ce ₂ CO ₃ 0.815 mol, 266 g and TTP (tetrakis (triphenylphos) Fin) palladium (0)) 8 mol% 11.6 g was added together with 500 mL of 1,4-dioxane and then refluxed. After 4 hours, the reaction was cooled to room temperature, _{500 ml of H 2} O was added, followed by extraction with EA. The solid obtained after filtering was recrystallized from EA (ethyl acetate) and Hx (normal hexane) to obtain 0.09 mol of [Intermediate 1-2] and 41.0 g (yield 73%).

3)

[Intermediate 1-2] [Intermediate 1-3]

[Intermediate 1-2] After dissolving 22.5mmol, 10g in 100 mL of MC (methylene chlorite), add 1 equivalent of NBS (N-bromosuccinimide), stir, extract with MC, recrystallize with Hx, 1-3] 20.3mmol, 10.62g (yield 90%) was obtained.

4)

[Intermediate 1-3] [Intermediate 1-4]

[Intermediate 1-3] 20.3 mmol, 10.62 g, (2-(methoxycarbonyl) phenyl) boronic acid 20.3 mmol 3.7 g was dissolved in THF (tetrahydrofuran) 100 mL/ H ₂ O 20 mL, and then K ₂ CO ₃ Add 60.9 mmol, 8.44g, stir under reflux, and then add 1mol% of TTP in sequence. When the reaction was completed after 12 h hours, the _{mixture was extracted with NH 4} Cl and CHCl ₃ , the organic layer was dried over anhydrous MgSO ₄ , filtered, and then concentrated under reduced pressure. The obtained organic material was dissolved in EA and recrystallized with EtOH to obtain [Intermediate 1-4] 14.21 mmol, 8.2g (yield 70%).

5)

[Intermediate 1-4] [Intermediate 1-5]

Dissolve 8.2 g of 14.21 mmol of [Intermediate 1-4] in 100 mL of THF, stir under reflux, and add 2 equivalents of _{BrMgCH 3 solution.} When the reaction was completed after reflux stirring, the solution was cooled to room temperature, quenched with NH ₄ Cl, extracted with EA, and the organic layer was dried over anhydrous MgSO ₄ , filtered, and then concentrated under reduced pressure. The obtained organic material was columned with EA:Hx (ethyl acetate:n-hexane) to obtain [Intermediate 1-5] 10.66 mmol, 6.2 g (yield 75%).

6)

[Intermediate 1-5] [Intermediate 1-6]

Dissolve 10.66 mmol and 6.2 g of [Intermediate 1-5] in 100 mL of CHCl _{3 (chloroform), add 10 mL of CH 3} SO ₃ H, and stir under reflux. After the reaction was completed, water was added, the solid was filtered, washed sequentially with EtOH and Hx, and dried with nitrogen to obtain [Intermediate 1-6] 8.5 mmol, 4.8 g (yield 80%).

7)

[Intermediate 1-6] [Intermediate 1-7]

Dissolve 8.5 mmol and 4.8 g of [Intermediate 1-6] in 100 mL of CHCl ₃ and add 4 equivalents of _{BBr 3 solution.} When the reaction was completed after stirring at room temperature, it was quenched with sodium thiosulfate _{, extracted with CHCl 3} , the organic layer was dried over anhydrous MgSO ₄ , filtered, and then concentrated under reduced pressure. The obtained organic material was purified by column using EA:Hx to obtain 7.48 mmol, 4.0g (yield 88%) of [Intermediate 1-7].

8)

[Intermediate 1-7] [Intermediate 1-8]

After dissolving 7.48 mmol and 4.0 g of [Intermediate 1-7] in 40 mL of NMP (N-methyl-2-pyrrolidone), _{6eq of K 2} CO was added and stirred under reflux. After the reaction was completed, water was added, the solid was filtered, washed sequentially with EtOH and Hx, and dried with nitrogen to obtain [Intermediate 1-8] 5.8 mmol, 2.9g (yield 78%).

9)

Intermediate 1-8] [Compound 1]

[Intermediate 1-8] After dissolving 5.8 mmol and 2.9 g in 50 mL of toluene, 23.2 mmol and 2.3 g of NatBuO were added ^{and stirred at 150 o} C. After stirring, diphenylamine 17.4 mmol, 2.9 g and BTP (bis(tri-t-butylphos) Fin) palladium (0)) 0.058 mmol 0.03g is added sequentially. After 12 hours, the reaction was finished, quenched with NH ₄ Cl, extracted with EA, dried over anhydrous MgSO ₄ , filtered, and then concentrated under reduced pressure. The obtained organic material was purified by column using EA:Hx to obtain 8 mmol 2.1g (yield 48%) of compound 1.

Synthesis example 2: Synthesis of compound 8

One)

[Intermediate 1-2] [Intermediate 8-1]

After dissolving 10g of [Intermediate 1-2] 22.5mmol in MC 100mL, 2 equivalents of NBS were added, stirred, and after the reaction was completed, the mixture was extracted with MC _{, dried and filtered with anhydrous MgSO 4} , and then concentrated under reduced pressure. The obtained organic material was dissolved in EA and recrystallized with Hx to obtain [Intermediate 8-1] 16.2 mmol 9.77 g (Yield=72%).

2)

[Intermediate 8-1] [Intermediate 8-2]

[Intermediate 8-1] 16.2 mmol 9.77g, (2-hydroxyphenyl) boronic acid 16.2 mmol 2.23g _{was dissolved in THF 100mL/ H 2} O 20mL, K ₂ CO ₃ 6.7g was added, stirred under reflux and TTP 1mol% Put them in order. After 12 h, the reaction was completed, quenched with NH ₄ Cl, extracted with EA, dried over anhydrous MgSO ₄ , filtered, and then concentrated under reduced pressure. The obtained organic material was dissolved in EA and recrystallized with EtOH to obtain [Intermediate 8-2] 91 mmol 5.49g (yield 55%).

3)

[Intermediate 8-4] [Intermediate 8-5]

Dissolve 3.8 g of 7.13 mmol of [Intermediate 8-4] in 100 mL of CHCl _{3 and add 4 equivalents of BBr3 solution.} When the reaction was completed after stirring at room temperature, it was quenched with sodium thiosulfate _{, extracted with CHCl 3} , the organic layer was dried over anhydrous MgSO ₄ , filtered, and then concentrated under reduced pressure. The obtained organic material was columned with EA:Hx to obtain [Intermediate 8-5] 6.4 mmol 3.3 g (yield 90%).

4)

[Intermediate 8-5] [Intermediate 8-6]

After dissolving 3.3 g of 6.4 mmol of [Intermediate 8-5] in 40 mL of NMP, _{6 eq of K 2} CO 3 was added and stirred under reflux. When the reaction was completed, water was added, the solid was filtered, washed with ethanol and hexane, and dried with nitrogen to obtain [Intermediate 8-6] 5.7 mmol 2.7 g (yield 89%).

5)

[Intermediate 8-3] [Compound 8]

After dissolving 2.7 g of 5.7 mmol of P-1 in 50 mL of toluene, 2.2 g of NatBuO was added, and after stirring at 150°C, 17.4 mmol of diphenylamine 2.9 g and 0.058 mmol of BTP 0.03 g were sequentially added. After 12 h, the reaction was completed, quenched with NH ₄ Cl, extracted with EA, dried over anhydrous MgSO ₄ , filtered, and then concentrated under reduced pressure. The obtained organic material was columned with EA:Hx to obtain compound 8, 3.1 mmol 2.3g (yield 55%).

Synthesis example 3: Synthesis of compound 6

One)

[Intermediate 8-3] [Compound 6]

[Intermediate 8-3] Using 7.5 mmol, 3.5 g and 17.2 mmol of N-(4-tert-butyl-phenyl)-[1,1'-biphenyl]-2-amine, 5.2 g, of Synthesis Example 4 In the same manner as in 7), compound 6, 3.2 mmol, 3.2g (yield 43%) was obtained.

Synthesis Example 4: Synthesis of Compound 10

One)

[Intermediate 1-2] [Intermediate 10-1]

[Intermediate 1-2] After dissolving 22.5 mmol, 10 g in 100 mL of MC, 1 equivalent of NBS was added, stirred, and after the reaction was completed, extracted with MC, the organic layer was dried over anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The obtained organic material was dissolved again with MC and recrystallized with Hx to obtain 10.62 g (yield 90%) of [Intermediate 10-1].

2)

[Intermediate 10-1] [Intermediate 10-2]

[Intermediate 10-1] 20.3 mmol 10.62g, (2-(methylthio)phenyl) boronic acid 20.3mmol, 3.4g _{dissolved in THF 100mL/ H 2} O 20mL, K ₂ CO ₃ 60.9 mmol, 8.44g added and refluxed After stirring, 1 mol% of TTP is sequentially added. After 12 hours, the reaction was finished, quenched with NH ₄ Cl, extracted with EtOAc, the organic layer was dried over anhydrous MgSO ₄ , filtered, and then concentrated under reduced pressure. The obtained organic material was dissolved in EA and recrystallized with EtOH to obtain [Intermediate 10-2] 14.21 mmol 8.1g (yield 70%).

3)

[Intermediate 10-2] [Intermediate 10-3]

Dissolve 14.21mmol and 8.1g of [Intermediate 10-2] in 100mL of AcOH, and then add 1 equivalent of _{H 2} O _2. When the reaction was completed, extraction was performed with EA, the organic layer was dried over anhydrous MgSO ₄ , filtered, and then concentrated under reduced pressure. The obtained organic material was columned only with EA to obtain [Intermediate 10-3] 12.8 mmol, 4.5g (yield 90%).

4)

[Intermediate 10-3] [Intermediate 10-4]

After dissolving 12.8 mmol and 4.5 g of [Intermediate 10-4] in 50 mL of MC, 10 mL of TfOH (trifluoromethane sulfonic acid, Triflic acid) was added and stirred. Upon completion of the reaction, 50 mL of water and 20 mL of pyridine were added, followed by stirring. When the reaction was completed, the mixture was extracted with MC, the organic layer was dried over anhydrous MgSO ₄ , filtered, and then concentrated under reduced pressure. The obtained organic material was dissolved in MC and recrystallized with EtOH to give [Intermediate 10-4] 8.5 mmol, 4.7 g (yield 66%).

5)

[Intermediate 10-4] [Intermediate 10-5]

Dissolve 8.5 mmol and 4.7 g of [Intermediate 10-4] in 100 mL of CHCl ₃ and add 4 equivalents of _{BBr 3 solution.} When the reaction was completed after stirring at room temperature, it was quenched with sodium thiosulfate _{, extracted with CHCl 3} , the organic layer was dried over anhydrous MgSO ₄ , filtered, and then concentrated under reduced pressure. The obtained organic material was columned with EA:Hx to obtain [Intermediate 10-5] 7.48 mmol, 3.9 g (yield 88%).

6)

[Intermediate 10-5] [Intermediate 10-6]

After dissolving 7.48 mmol and 3.9g of [Intermediate 10-5] in 40 mL of NMP, _{6eq of K 2} CO ₃ was added and stirred under reflux. When the reaction was completed, water was added, the solid was filtered, and washed with ethanol and hexane to obtain [Intermediate 10-6] 6.6 mmol, 3.2 g (yield 88%).

7)

[Intermediate 10-6] [Compound 10]

[Intermediate 10-6] Dissolve 6.6 mmol, 3.2 g in 60 mL of toluene, add 26.4 mmol of NatBuO, 2.5 g, and stir at 150 ^o C. After stirring, 6.7 mmol of 4-(tert-butyl)-N-phenylaniline, 1.2 g and BTP 0.058 mmol, 0.03g are added sequentially. After 12h, when the reaction was completed, the _{mixture was quenched with NH 4} Cl, extracted, the organic layer was dried over anhydrous MgSO ₄ , filtered, and then concentrated under reduced pressure. The obtained organic material was columned with EA:Hx to give compound 10, 3.3 mmol, 2.8g (yield 49%). The LC-Mass measurement graph of Compound 10 is shown in FIG. 3 below.

Synthesis Example 5: Synthesis of Compound 26

One)

[Intermediate 1-3] [Intermediate 26-1]

[Intermediate 1-3] 9.2 mmol, 5.0g, (5-(tert-butyl)-2-(methoxycarbonyl)phenyl) the same method as in 4) of Synthesis Example 1 using 2.8 g of 12.0 mmol of boronic acid As a result, [Intermediate 26-1] 5.5 mmol, 3.5g (yield 60%) was obtained.

2)

[Intermediate 26-1] [Intermediate 26-2]

[Intermediate 26-1] Using 5.5 mmol and 3.5g, [Intermediate 26-2] 3.9 mmol and 2.5g (yield 60%) were obtained in the same manner as in Synthesis Example 1 5).

3)

[Intermediate 26-2] [Intermediate 26-3]

[Intermediate 26-3] 5.3 mmol, 3.3 g (yield 85%) were obtained in the same manner as in Synthesis Example 1 6) using 6.3 mmol and 4.0g.

4)

[Intermediate 26-3] [Intermediate 26-4]

[Intermediate 26-3] 4.9 mmol, 2.9 g (yield 92%) of [Intermediate 26-4] were obtained in the same manner as in 7) of Synthesis Example 1 using 5.3 mmol and 3.3g.

5)

[Intermediate 26-4] [Intermediate 26-5]

[Intermediate 26-4] 4.2 mmol, 2.3 g (yield 85%) of [Intermediate 26-5] were obtained in the same manner as 8) of Synthesis Example 1 using 4.9 mmol and 2.9g.

6)

[Intermediate 26-5] [Compound 26]

[Intermediate 26-5] Using 4.2 mmol, 2.3g and 9.6 mmol of N-(o-tolyl)-[1,1'-biphenyl]-2-amine, 2.5g, the same method as 9) of Synthesis Example 1 To obtain [Compound 26] 2.1 mmol, 2.1g (yield 50%).

Synthesis Example 6: Synthesis of Compound 43

One)

[Intermediate 10-6] [Compound 43]

[Intermediate 10-6] Compound 43, 2.8 mmol, 2.1g (yield 39%) were obtained in the same manner as in 7) of Synthesis Example 4 using 7.2 mmol, 3.5 g, and carbazole 17.4 mmol, and 2.9g.

< Example >

Example One

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1300Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by vacuum depositing the following compound [HI-A] to a thickness of 600Å on the ITO transparent electrode prepared as described above. The following compound [HAT-CN] (50Å) and the following compound [HT-B] (600Å) were sequentially vacuum-deposited on the hole injection layer to form a hole transport layer. Then, in forming a light emitting layer on the hole transport layer, the present invention The [Compound 1] of [BH-A] was doped at 2.5 wt% compared to [BH-A] and vacuum deposited to a thickness of 200 Å. In forming the electron transport layer on the light emitting layer thus constructed, 50Å of [ET-A] was deposited, and then 300Å of [ET-B] and Liq at a ratio of 1:1 was vacuum deposited. A negative electrode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1,000 Å on the electron transport layer.

In the above process, the deposition rate of organic material was maintained at 0.4 ~ 0.9 Å/sec, the deposition rate of lithium fluoride at the negative electrode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 1 Х 10 ^{− Maintaining 7} to 5 Х 10 ^-8 torr, an organic light emitting device was manufactured. For the life of the device, the driving voltage and luminous efficiency of the organic light-emitting device ^{were measured at a current density of 10 mA/cm 2} _{, and the time (T 90} ) to become 90% of the initial luminance at a current density of ^{20 mA/cm 2} . The results are shown in Table 1 below.

Example 2.

In Example 1, an organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 6 was used instead of Compound 1.

Example 3.

In Example 1, an organic light-emitting device was manufactured in the same manner as in Example 1, except that compound 8 was used instead of compound 1.

Example 4.

In Example 1, an organic light-emitting device was manufactured in the same manner as in Example 1, except that compound 10 was used instead of compound 1.

Example 5.

In Example 1, an organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 26 was used instead of Compound 1.

Example 6.

In Example 1, an organic light-emitting device was manufactured in the same manner as in Example 1, except that compound 43 was used instead of compound 1.

Example 7.

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

Example 8.

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

Example 9.

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

Example 10.

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

Example 11.

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

Example 12.

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

Comparative example One.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that [BD-A] was used instead of Compound 1 in Example 1 above.

Comparative example 2.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that [BD-B] was used instead of Compound 1 in Example 1 above.

Comparative example 3.

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

Comparative example 4.

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

Comparative example 5.

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

Comparative example 6.

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

Example Host Dopant @ 10 mA / cm ² @ 20 mA / cm ² Voltage(V) Efficiency (cd/A) CIE (x,y) Life (T ₉₀ , hr) Example 1 [BH-A] Compound 1 3.4 9.0 (0.133, 0.138) 170 Example 2 [BH-A] Compound 6 3.5 8.9 (0.133, 0.142) 190 Example 3 [BH-A] Compound 8 4.0 7.9 (0.132, 0.139) 210 Example 4 [BH-A] Compound 10 3.3 9.1 (0.133, 0.142) 190 Example 5 [BH-A] Compound 26 3.8 8.4 (0.133, 0.141) 170 Example 6 [BH-A] Compound 43 3.5 8.3 (0.133, 0.140) 210 Example 7 [BH-B] Compound 1 3.2 8.3 (0.133, 0.138) 150 Example 8 [BH-C] Compound 1 3.6 8.4 (0.133, 0.138) 200 Example 9 [BH-B] Compound 6 3.3 8.4 (0.133, 0.138) 160 Example 10 [BH-C] Compound 6 3.7 8.2 (0.133, 0.138) 190 Example 11 [BH-B] Compound 10 3.4 8.6 (0.133, 0.138) 170 Example 12 [BH-C] Compound 10 3.3 8.1 (0.133, 0.138) 220 Comparative Example 1 [BH-A] [BD-A] 3.9 7.1 (0.133, 0.139) 80 Comparative Example 2 [BH-A] [BD-B] 3.6 6.5 (0.133, 0.138) 85 Comparative Example 3 [BH-B] [BD-A] 3.6 7.2 (0.133, 0.139) 70 Comparative Example 4 [BH-B] [BD-B] 3.8 6.8 (0.133, 0.138) 90 Comparative Example 5 [BH-C] [BD-A] 4.0 7.0 (0.133, 0.139) 95 Comparative Example 6 [BH-C] [BD-B] 4.2 6.7 (0.133, 0.138) 90

From the results of the above table, the compound represented by Formula 1 according to the present invention can be used as a fluorescent dopant in an organic light emitting device. In the case of an organic light-emitting device using this, it shows high efficiency and long life.

Examples 7 to 12 show the results of combination experiments with hosts of different personalities, and exhibit excellent fluorescence characteristics even in experiments with different types of hosts.

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

Claims (15)

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

In Formula 1,
X1 and X2 are the same as or different from each other, and each independently O or S,
Y is O, S or CRdRe,
Rd, Re, and R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a to c are each an integer of 0 to 4,
When a to c are each an integer of 2 or more, the substituents in parentheses are the same as or different from each other. The method according to claim 1,
Formula 1 is a compound represented by the following Formula 2:
[Formula 2]

In Formula 2,
X1, X2, Y, R1, R4, R5 and a are as defined in Formula 1,
R21 and R31 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or heteroaryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
b1 and c1 are each an integer of 0 to 4, and when b1 and c1 are each 2 or more, the substituents in parentheses are the same as or different from each other,
m1 and m2 are each 0 or 1, m1+b1 is an integer of 0-4, and m2+c1 is an integer of 0-4. The method according to claim 1,
Formula 1 is a compound represented by the following formula 3 or 4:
[Formula 3]

[Formula 4]

In Formulas 3 and 4,
X1, X2, Y, R1, R4, R5 and a are as defined in Formula 1,
R6, R7, R21 and R31 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar21 to Ar24 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
b11 and c11 are each an integer of 0 to 3, and when b11 and c11 are each 2 or more, the substituents in parentheses are the same as or different from each other,
e and f are each an integer of 0 to 8, and when e and f are each 2 or more, the substituents in parentheses are the same as or different from each other. The method of claim 3,
The Ar21 to Ar24 are the same as or different from each other, and each independently a compound represented by the following Formula 3-1 or 3-2:
[Chemical Formula 3-1]

[Chemical Formula 3-2]

In Formulas 3-1 and 3-2,
X3 is O, S, CRR' or NR",
X4 to X6 are the same as or different from each other, and each independently CRf, or N,
R, R', R", Rf, R8 and R9 are the same as or different from each other, and each independently hydrogen; deuterium; halogen group; cyano group; silyl group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted Cycloalkyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group,
g is an integer from 0 to 7, and when g is 2 or more, R8 is the same as or different from each other,
h is an integer of 0 to 2, and when h is 2, R9 is the same as or different from each other. The method according to claim 1,
Formula 1 is a compound represented by any one of the following structures:

. A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to any one of claims 1 to 5 Light-emitting element. The method of claim 6,
The organic material layer comprises 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,
The organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound. The method of claim 6,
The organic material layer includes an emission layer, and the emission layer includes the compound. The method of claim 6,
The organic light emitting device is that the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 1A:
[Formula 1A]

In Formula 1A,
L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R24 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
p is an integer from 0 to 6,
When p is 2 or more, R24 is the same as or different from each other. The method of claim 10,
L103 to L106 are the same as or different from each other, and each independently a direct bond; Or an organic light-emitting device selected from the following structures:

. The method of claim 10,
Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Or an organic light-emitting device selected from the following structures:

. The method of claim 6,
The organic material layer includes an emission layer, and the emission layer includes a compound represented by the following Formula 1B:
[Formula 1B]

In Formula 1B,
L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R25 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
q is an integer from 0 to 7,
When q is 2 or more, R25 is the same as or different from each other. The method of claim 13,
L107 to L109 are the same as or different from each other, and each independently a direct bond; Or an organic light-emitting device selected from the following structures:

. The method of claim 13,
Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; Or an organic light-emitting device selected from the following structures:

.

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