KR20190111688A - Multicyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound of chemical formula 1 and an organic light emitting device comprising the same. The compound described in the present specification can be used as a material of an organic material layer of the organic light emitting device. When manufacturing the organic light emitting device comprising the compound according to at least one embodiment, it is possible to obtain the organic light emitting device having high efficiency and long lifespan.

Description

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

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 the organic semiconductor material. The organic light emitting device can be classified into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a light emitting element of the form. The second is a light emitting device in which holes and / or electrons are injected into the organic semiconductor material layer that interfaces with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows. Such organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

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

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

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

Korean Patent 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 the following formula (1).

[Formula 1]

In Chemical Formula 1,

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

Ra, Rb, Rc 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 groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted amine group; 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.

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

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

FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
3 depicts a LC-Mass measurement graph of compound 12.

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

The present specification provides a compound represented by the following Formula 1. When using the compound represented by the following formula (1) in the organic material layer of the organic light emitting device, the efficiency is always at the time of manufacturing the organic light emitting device using a derivative having a core 'fluoranthene' having a high quantum efficiency.

Also. The compound according to the exemplary embodiment of the present application minimizes the separation of HOMO and LUMO to move very efficiently in the movement of electrons and electrons to form excitons, thereby maximizing the emission characteristics and having a high structure having a narrow half-width of the emission spectrum. When the blue organic light emitting device is manufactured using this, it can have a high color reproducibility in the upper emission as well as the lower emission.

 [Formula 1]

In Chemical Formula 1,

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

Ra, Rb, Rc 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 groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted amine group; 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, this means that it may further include other components, without excluding other components unless specifically stated otherwise.

In this specification, when a member is located "on" another member, this includes not only when a member is in contact with another member but also when another member exists between the two members.

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

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

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Cyano group (-CN); Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" 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 linked.

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 a chemical formula of -SiY _a Y _b Y _C , wherein Y _a , Y _b and Y _c are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group, but are not limited thereto. Do not.

In the present specification, the boron group may be represented by a chemical formula of -BY _d Y _e , wherein Y _d and Y _e are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group may include, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, and phenylboron group.

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

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one 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, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but is not limited thereto.

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

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

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, may be a polycyclic aryl group. The arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.

Specific examples of the arylamine group include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, diphenylamine group, phenylnaphthylamine group, biphenylphenylamine group, dibiphenylamine group, and fluorine. And a phenylphenyl group, 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, may be a polycyclic heteroaryl group. The heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.

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

In the present specification, the arylalkylamine group means an amine group substituted with an aryl group and 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 preferably has 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 monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, peryllenyl group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may 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-diphenyl fluorenyl group). However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si, and Se as hetero atoms, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include, for example, pyridine group, pyrrole group, pyrimidine group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, carbazole group Etc., but is not limited thereto.

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

In the present specification, in a substituted or unsubstituted ring in which adjacent groups are bonded to each other, a “ring” means a hydrocarbon ring; Or heterocycle.

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

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

In the present specification, the heterocycle includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms include one or more atoms selected from the group consisting of N, O, P, S, Si, Se, and the like. can do. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a 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 one 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 alkyl group having 1 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another exemplary embodiment, Ra and Rb are the same as or different from each other, and are 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; Substituted or unsubstituted propyl group; Substituted or unsubstituted butyl group; 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; Profile group; Butyl group; Pentyl group; Or a hexyl group.

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

According to an exemplary embodiment of the present specification, the 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 aryl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another exemplary embodiment, R1 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

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

In another exemplary embodiment, R1 is hydrogen; heavy hydrogen; Or methyl group.

According to an exemplary embodiment of the present specification, the a is an integer of 0 to 2, when a is 2 two R1 are the same as or different from each other.

According to an exemplary embodiment of the present specification, 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 alkyl group having 1 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to 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 alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

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 alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

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

According to another exemplary embodiment, R4 and R5 are hydrogen.

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, two or more R2 are the same as or different from each other, and when c is 2 or more, two or more R3 are the same or different from each other. Do.

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

According to an exemplary embodiment of the present specification, the R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Or a substituted or unsubstituted heteroring group.

In another exemplary embodiment, R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heteroring 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, Formula 1 may be represented by the following formula (2).

[Formula 2]

In Chemical Formula 2,

X1, X2, 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 groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted amine group; 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, the 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 alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to 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 alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

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 alkyl group having 1 to 20 carbon atoms.

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); Substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Substituted or unsubstituted propyl group; Or a substituted or unsubstituted butyl group.

In another exemplary embodiment, R21 and R31 are the same as or different from each other, and each independently hydrogen; heavy 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 R31 are the same or different from each other. Do.

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

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

According to another exemplary embodiment, m1 and m2 are 1, and b1 and c1 are each an integer 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 arylene group having 6 to 60 carbon atoms.

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 arylene group having 6 to 30 carbon atoms.

According to another exemplary embodiment, 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 are 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 are each independently a phenylene group unsubstituted or substituted with a methyl group.

According to another exemplary embodiment, 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 combine with 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 combine with each other to form a substituted or unsubstituted hetero ring 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 substituted or unsubstituted with deuterium, cyano group, halogen group, silyl group, or alkyl group having 1 to 10 carbon atoms Aryl group; Or a deuterium, cyano group, halogen group, silyl group or a C 2 to C 30 heteroaryl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, or adjacent groups are bonded to each other to deuterium, cyano group, halogen group, silyl group or A heterocyclic ring having 2 to 30 carbon atoms is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted pyridine group; Substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted triazine group, or adjacent groups combine with 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 phenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group, or alkyl group having 1 to 10 carbon atoms; A biphenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms; Terphenyl groups unsubstituted or substituted with deuterium, cyano groups, halogen groups, silyl groups or alkyl groups having 1 to 10 carbon atoms; Naphthyl group which is unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms; Dibenzofuran group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms; Dibenzothiophene group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms; Fluorenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms; Pyridine groups unsubstituted or substituted with deuterium, cyano groups, halogen groups, silyl groups or alkyl groups having 1 to 10 carbon atoms; Pyrimidine groups unsubstituted or substituted with deuterium, cyano groups, halogen groups, silyl groups or alkyl groups having 1 to 10 carbon atoms; Or a triazine group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms, or adjacent groups are bonded to each other to deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms To form a substituted or unsubstituted carbazole.

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 phenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl group; A biphenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl group; Deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl group terphenyl group; Deuterium, cyano, halogen, methyl, tert-butyl or trimethylsilyl groups; Dibenzofuran group unsubstituted or substituted with deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl group; Dibenzothiophene group unsubstituted or substituted with deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl group; Fluorenyl groups unsubstituted or substituted with deuterium, cyano, halogen, methyl, tert-butyl or trimethylsilyl groups; Pyridine groups unsubstituted or substituted with deuterium, cyano, halogen, methyl, tert-butyl or trimethylsilyl groups; Pyrimidine groups unsubstituted or substituted with deuterium, cyano, halogen, methyl, tert-butyl or trimethylsilyl groups; Or a triazine group unsubstituted or substituted with deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl group, or adjacent groups are bonded to each other to deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl To form a carbazole substituted or unsubstituted with a group.

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl group; Biphenyl group; Fluorenyl group substituted with a methyl group; dibenzofuran group unsubstituted or substituted with tert-butyl group; Or a dibenzothiophene group, or adjacent groups combine with 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 the following Chemical Formula 3 or 4.

[Formula 3]

[Formula 4]

In Chemical Formulas 3 and 4,

X1, X2, 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 groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted amine group; 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 or different from each other.

In Chemical 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 each 0 or 1.

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 alkyl group having 1 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to 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 alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

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 alkyl group having 1 to 20 carbon atoms.

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); Substituted or unsubstituted methyl group; Or a substituted or unsubstituted tert-butyl group.

According to another exemplary embodiment, R6 and R7 are hydrogen.

According to one embodiment of the present specification, e and f are integers of 0 to 8, and when e is 2 or more, two or more R6 are the same as or different from each other, and when f is 2 or more, two 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 heteroaryl group having 2 to 60 carbon atoms.

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 heteroaryl group having 2 to 30 carbon atoms.

In another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and each independently substituted or unsubstituted with deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms Aryl group; Or a heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms.

According to another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted pyridine group; 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 phenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms; A biphenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms; Terphenyl groups unsubstituted or substituted with deuterium, cyano groups, halogen groups, silyl groups or alkyl groups having 1 to 10 carbon atoms; Naphthyl group which is unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms; Dibenzofuran group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms; Dibenzothiophene group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms; Fluorenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group or alkyl group having 1 to 10 carbon atoms; Pyridine groups unsubstituted or substituted with deuterium, cyano groups, halogen groups, silyl groups or alkyl groups having 1 to 10 carbon atoms; Pyrimidine groups unsubstituted or substituted with deuterium, cyano groups, halogen groups, silyl groups or alkyl groups having 1 to 10 carbon atoms; Or a triazine group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group or 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 phenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl group; A biphenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl group; Deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl group terphenyl group; Deuterium, cyano, halogen, methyl, tert-butyl or trimethylsilyl groups; Dibenzofuran group unsubstituted or substituted with deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl group; Dibenzothiophene group unsubstituted or substituted with deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl group; Fluorenyl groups unsubstituted or substituted with deuterium, cyano, halogen, methyl, tert-butyl or trimethylsilyl groups; Pyridine groups unsubstituted or substituted with deuterium, cyano, halogen, methyl, tert-butyl or trimethylsilyl groups; Pyrimidine groups unsubstituted or substituted with deuterium, cyano, halogen, methyl, tert-butyl or trimethylsilyl groups; Or a triazine group unsubstituted or substituted with deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl group.

According to another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, methyl group, tert-butyl group or trimethylsilyl group; Biphenyl group; Fluorenyl group substituted with a methyl group; dibenzofuran group unsubstituted or substituted with tert-butyl group; Or a dibenzothiophene 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 may be represented by the following Chemical Formula 3-1 or 3-2.

[Formula 3-1]

[Formula 3-2]

In Chemical 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 CRd or N,

R, R ', R ", Rd, R8 and R9 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; 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 heteroaryl 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 from 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 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; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group Or a substituted or unsubstituted 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 methyl group.

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

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

In another exemplary embodiment, X4 to X6 are CRd.

In one embodiment of the present specification, Rd is hydrogen; heavy hydrogen; Halogen group; Silyl groups; Cyano group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Rd is hydrogen; heavy hydrogen; Halogen group; Silyl groups; Cyano group; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, Rd is hydrogen; heavy hydrogen; Halogen group; Trimethylsilyl group; Substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Substituted or unsubstituted propyl group; Substituted or unsubstituted butyl group; Substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

In another exemplary embodiment, Rd is hydrogen; heavy hydrogen; Halogen group; Trimethylsilyl group; Methyl group; Or tert-butyl group.

According to an exemplary embodiment of the present specification, the R8 and R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl groups; 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 groups; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to 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 groups; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

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 groups; Substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Substituted or unsubstituted propyl group; Or a substituted or unsubstituted butyl 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); Trimethylsilyl group; Methyl group; Or tert-butyl group.

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

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

Compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by the production method described below. Substituents may be combined 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 of the compound and the energy bandgap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.

In the present invention, a compound having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In addition, in the present invention, the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents into the core structure of the above structure.

Moreover, the compound which has the intrinsic property of the introduced substituent can be synthesize | combined by introducing various substituents into the core structure of the above structure. For example, by incorporating a substituent mainly used in the hole injection layer material, the hole transport material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic light emitting device into the core structure, it is possible to synthesize a material satisfying the requirements of each organic material layer. Can be.

Moreover, the compound which has the intrinsic property of the introduced substituent can be synthesize | combined by introducing various substituents into the core structure of the above structure. For example, by incorporating a substituent mainly used in the hole injection layer material, the hole transport material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic light emitting device into the core structure, it is possible to synthesize a material satisfying the requirements of each organic material layer. Can be.

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 at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound described above.

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

The organic material layer of the present specification may include a structure of Formula 1A as a material of the host of the light emitting layer.

[Formula 1A]

In Chemical Formula 1A,

L103 to L106 are the same as or different from each other, and each independently a direct bond; 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; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R 24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; 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 one 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 heteroarylene group having 2 to 60 carbon atoms.

In one 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 heteroarylene group having 2 to 40 carbon atoms.

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

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

According to an exemplary embodiment of the present specification, 104 is a phenylene group.

According to an exemplary embodiment of the present disclosure, L105 and L106 is a direct bond.

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

In one embodiment of the present specification, R24 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In one 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 having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

In one 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 having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.

In another exemplary embodiment, R24 is hydrogen.

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

In one embodiment of the present specification, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another exemplary embodiment, 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 unsubstituted or substituted with a C6-60 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; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted furan group; Substituted or unsubstituted benzothiophene group; Substituted or unsubstituted benzofuran group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted benzofluorene group; Substituted or unsubstituted indole carbazole group; Substituted or unsubstituted pyridyl group; Substituted or unsubstituted isoquinolyl group; Substituted or unsubstituted quinolyl group; Substituted or unsubstituted quinazolyl group; Substituted or unsubstituted triazine group; Substituted or unsubstituted benzimidazole group; Substituted or unsubstituted benzoxazole group; Substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; 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 groups; Triphenylene group; Dibenzofuran group unsubstituted or substituted with an aryl group; Naphthobenzofuran group; Dibenzothiophene group unsubstituted or substituted with an aryl group; Carbazole groups 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; 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; A benzofluorene group unsubstituted or substituted with an alkyl group or an aryl group; Indole carbazole groups; Pyridyl groups; Isoquinolyl group unsubstituted or substituted with an aryl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with an aryl group; Triazine group unsubstituted or substituted with an aryl group; Benzimidazole groups unsubstituted or substituted with an aryl group; Benzoxazole group unsubstituted or substituted by an aryl group; Benzothiazole group unsubstituted or substituted with an aryl group; A dihydroacridine group unsubstituted or substituted with an alkyl group or an aryl group; Xanthene group unsubstituted or substituted by 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 groups; Triphenylene group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Naphthobenzofuran group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Carbazole groups 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; Thiophene group unsubstituted or substituted with a phenyl group; 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; Indole carbazole groups; Pyridyl groups unsubstituted or substituted with a phenyl group or a naphthyl group; Isoquinolyl group unsubstituted or substituted with a phenyl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with a phenyl group; Triazine group unsubstituted or substituted with a phenyl group; Benzimidazole groups unsubstituted or substituted with a phenyl group; Benzoxazole group unsubstituted or substituted by a phenyl group; Benzothiazole group unsubstituted or substituted with a phenyl group; A dihydroacridine group unsubstituted or substituted with a methyl group or a phenyl group; Xanthene group unsubstituted or substituted by the methyl group or the phenyl group; Or a dibenzosilol group unsubstituted or substituted with a methyl group or a phenyl group.

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

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

The organic light-emitting device of the present specification may include a structure of Formula 1B as a material of a host of the light emitting layer.

[Formula 1B]

In Chemical Formula 1B,

L107 to L109 are the same as or different from each other, and each independently a direct bond; 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; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R 25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; 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 one embodiment of the present specification, R25 is hydrogen; heavy hydrogen; Halogen group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heteroring group.

In one embodiment of the present specification, R25 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In one 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 having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

In one 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 having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.

In another exemplary embodiment, R25 is hydrogen.

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

In one 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 heteroarylene group having 2 to 60 carbon atoms.

In one 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 heteroarylene group having 2 to 40 carbon atoms.

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

In yet one embodiment, the 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 the following structures.

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

In one embodiment of the present specification, Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another exemplary embodiment, 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 unsubstituted or substituted with a C6-60 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; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted furan group; Substituted or unsubstituted benzothiophene group; Substituted or unsubstituted benzofuran group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted benzofluorene group; Substituted or unsubstituted indole carbazole group; Substituted or unsubstituted pyridyl group; Substituted or unsubstituted isoquinolyl group; Substituted or unsubstituted quinolyl group; Substituted or unsubstituted quinazolyl group; Substituted or unsubstituted triazine group; Substituted or unsubstituted benzimidazole group; Substituted or unsubstituted benzoxazole group; Substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; 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; Dibenzofuran group unsubstituted or substituted with an aryl group; Naphthobenzofuran group; Dibenzothiophene group unsubstituted or substituted with an aryl group; Carbazole groups 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; 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; A benzofluorene group unsubstituted or substituted with an alkyl group or an aryl group; Indole carbazole groups; Pyridyl groups; Isoquinolyl group unsubstituted or substituted with an aryl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with an aryl group; Triazine group unsubstituted or substituted with an aryl group; Benzimidazole groups unsubstituted or substituted with an aryl group; Benzoxazole group unsubstituted or substituted by an aryl group; Benzothiazole group unsubstituted or substituted with an aryl group; A dihydroacridine group unsubstituted or substituted with an alkyl group or an aryl group; Xanthene group unsubstituted or substituted by 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 groups; Triphenylene group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Naphthobenzofuran group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Carbazole groups 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; Thiophene group unsubstituted or substituted with a phenyl group; 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; Indole carbazole groups; Pyridyl groups unsubstituted or substituted with a phenyl group or a naphthyl group; Isoquinolyl group unsubstituted or substituted with a phenyl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with a phenyl group; Triazine group unsubstituted or substituted with a phenyl group; Benzimidazole groups unsubstituted or substituted with a phenyl group; Benzoxazole group unsubstituted or substituted by a phenyl group; Benzothiazole group unsubstituted or substituted with a phenyl group; A dihydroacridine group unsubstituted or substituted with a methyl group or a phenyl group; Xanthene group unsubstituted or substituted by the methyl group or the phenyl group; Or a dibenzosilol group unsubstituted or substituted with a methyl group or a phenyl group.

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

The organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is 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 in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying 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 above-described 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, the hole injection layer or a hole transport layer may include the above-described compound.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound described above.

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

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes the aforementioned compound as a dopant of the light emitting layer, includes a fluorescent host or a phosphorescent host, and includes another organic compound, a metal, or a metal compound as a dopant. It may include.

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

According to an exemplary embodiment of the present invention, the organic material layer includes a light emitting layer, the light emitting layer may include the compound described above as a dopant of the light emitting layer, and may include the compound of Formula 1A or 1B as a post of the light emitting layer.

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

As another example, the organic material layer may include a light emitting layer, the light emitting layer may be included as a host of the above-described light emitting layer, and may include a dopant.

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

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

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

1 illustrates 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 light emitting layer (3).

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

For example, the organic light emitting diode may have a laminated structure as described below, but is not limited thereto.

(1) anode / hole transport layer / light emitting layer / cathode

(2) Anode / hole injection layer / hole transport layer / light emitting layer / cathode

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

(4) Anode / hole transport layer / light emitting layer / electron transport layer / cathode

(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 / cathode

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

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

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

(18) Anode / hole injection layer / hole transport layer / electron suppression layer / light emitting layer / hole blocking layer / electron injection and transport layer / cathode

For example, the organic light emitting device according to the present invention uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode to form an anode, 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 the above 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, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.

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

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

The hole injection layer is a layer that facilitates the 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, the highest occupied hole injection material The molecular orbital) is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto. The hole injection layer may have a thickness of 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing the hole injection characteristic from being lowered. When the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage that can be prevented.

The hole transport layer may serve to facilitate the transport of holes. As a hole transporting material, a material capable of transporting holes from an anode or a hole injection layer to be transferred to a light emitting layer is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, 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 suppression layer may be provided between the hole transport layer and the light emitting layer. The electron suppressing layer may be the aforementioned spiro compound or a material known in the art.

The emission layer may emit red, green, or blue light, and may be formed of a phosphor or a fluorescent material. The light emitting material is a material capable of emitting light in the visible 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 with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

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

When the light emitting layer emits red light, light emitting dopants include PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonateiridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium) and PQIr (tris (1-phenylquinoline) iridium Phosphor, such as octaethylporphyrin platinum (PtOEP), or a fluorescent substance such as Alq ₃ (tris (8-hydroxyquinolino) aluminum) may be used, but is not limited thereto. When the light emitting layer emits green light, a phosphor such as Ir (ppy) ₃ (fac tris (2-phenylpyridine) iridium) or a phosphor such as Alq3 (tris (8-hydroxyquinolino) aluminum) may be used as the light emitting dopant. However, the present invention is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant may be a phosphor such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, ditylbenzene (DSB), distriarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited thereto.

A hole suppression layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.

The electron transport layer may serve to facilitate the transport of electrons. As the electron transporting material, a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including 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 transporting layer is 1 nm or more, there is an advantage that the electron transporting property can be prevented from being lowered. If the thickness of the electron transporting layer is 50 nm or less, the thickness of the electron transporting layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There is an advantage to this.

The electron injection layer may play a role of smoothly injecting electrons. As the electron injection material, it has the ability to transport electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and The compound which is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

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

The hole blocking layer is a layer that blocks the reaching of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, 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, the present invention will be described in detail with reference to Examples. However, the embodiments according to the present disclosure may be modified in various other forms, and the scope of the present application is not interpreted to be limited to the embodiments described below. Embodiments of the present application are provided to more fully describe the present specification to those skilled in the art.

< Synthesis Example >

Synthesis Example 1 Synthesis of Compound 1

One)

                                     [Intermediate 1-1]

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

2)

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

[Intermediate 1-1] 0.125 mol, 43.4 g with (4-chloro-2-fluorophenyl) boronic acid 0.301 mol, 52.5 g with Ce ₂ CO ₃ 0.815 mol, 266 g with TTP (tetrakis (triphenyl) 11.6 g of phosphine) palladium (0)) was added together with 500 mL of 1,4-dioxane to reflux. After 4 hours, the reaction was cooled to room temperature, 500 ml of H ₂ O was added, and extracted with EA. After filtration, the obtained solid 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 22.5 mmol and 10 g in 100 mL of MC (Methylene chloride), add 1 equivalent of NBS ( N-Bromosuccinimide ), and after stirring, extracted with MC and recrystallized with Hx. [Intermediate 1-3] 20.3 mmol, 10.62 g (yield 90%) was obtained.

4)

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

[Intermediate 1-3] 20.3 mmol, 10.62 g, and 4.9 g of 24.3 mmol (2-bromophenyl) boronic acid were dissolved in 20 mL of THF (tetrahydrofuran) 100 mL / H ₂ O, followed by K ₂ CO ₃ 60.8 mmol, 8.40 Put g and reflux stir and add 2 mol% of BTP (bis (tri-t-butylphosphine) palladium (o)) sequentially. After the reaction was completed after 14 h, NH ₄ Cl (aq) was added thereto, extracted with CHCl ₃ , the organic layer was dried over anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The obtained organic material was dissolved in EA and recrystallized with EtOH to give 8.6 mmol, 5.2 g (yield 42%) of [Intermediate 1-4].

5)

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

[Intermediate 1-4] 8.6 mmol, 5.2 g and 30.3 mmol of K ₃ PO ₄ , 6.44 g were first added to 100 mL of toluene, followed by heating to 50 ^o C, followed by 2.0 mol% of Pd (OAc) 2 and 4.0 mol% of Sphos in that order. Put it in. After completion of the addition, the mixture was stirred at reflux for 4 hours. NH ₄ Cl (aq) was added thereto, diluted, and extracted with CHCl _{3. The} organic layer was dried over anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The obtained organic material was dissolved in CHCl ₃ and recrystallized with EtOH to obtain 3.7 mmol of [Intermediate 1-5] and 1.9 g (yield 42%).

6)

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

Dissolve 11.0 mmol and 5.7 g of [Intermediate 1-5] in 150 mL of CHCl ₃ , and slowly add 32.9 mmol and 8.3 g of BBr ₃ . After stirring at room temperature, the reaction was completed, quenched with sodium thiosulfate, extracted with CHCl _3, and the organic layer was dried over anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The obtained organic material was recrystallized from EA: Hx to obtain 9.77 mmol of [Intermediate 1-6] and 4.8 g (yield 89%).

7)

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

Dissolve 9.77 mmol and 4.8 g of [Intermediate 1-6] in 60 mL NMP (N-methyl-2-pyrrolidone), and add 58.6 mmol of K ₂ CO and 8.1 g. After the reaction, water was added, the solid was filtered, washed sequentially with EtOH and Hx, and dried with nitrogen to obtain [Intermediate 1-7] 9.3 mmol, 4.2 g (yield 95%).

8)

       [Intermediate 1-7] [Compound 1]

[Intermediate 1-7] After dissolving 9.3 mmol and 4.2 g in 70 mL of toluene, add 37.2 mmol and 3.6 g of NatBuO, stir at 130 ^° C., and then add 32.6 mmol, 5.5 g of diphenylamine, and 0.07 g of BTP 0.14 mmol in that order. . After 10 hours, the reaction was quenched with NH ₄ Cl, extracted with EA (ethyl acetate), and the organic layer was dried over anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The obtained organic material was purified by column using EA: Hx to obtain 2.6 mmol (yield 39%) of compound 1 (3.6 mmol).

Synthesis Example 2 Synthesis of Compound 2

        [Intermediate 1-7] [Compound 2]

[Intermediate 1-7] Compound 2, 3.5 mmol, using 8.4 mmol, 3.8 g and 29.4 mmol of 4- (tert-butyl) -N-phenylaniline, 6.6 g, using the same method as in 8) of Synthesis Example 1 2.9 g (yield 39%) were obtained.

Synthesis Example 3 Synthesis of Compound 4

     [Intermediate 1-7] [Compound 4]

Intermediate 1-7 The same procedure as in Synthesis Example 8) using 8.4 mmol, 3.8 g, and 27.1 mmol, 7.6 g of N- (o-tolyl)-[1,1'-biphenyl] -4-amine To give compound 4, 3.9 mmol, 3.5g (yield 46%).

Synthesis Example 4 Synthesis of Compound 7

     [Intermediate 1-7] [Compound 7]

[[Intermediate 1-7] Synthesis Example 1 using 10.2 mmol, 4.6 g, and 35.7 mmol, 9.7 g of 2'-methyl-N- (o-tolyl)-[1,1'-biphenyl] -4-amine Compound 7, 4.1 mmol, and 3.8 g (yield 39%) were obtained using the same method as in 8).

Synthesis Example 5 Synthesis of Compound 12

      [Intermediate 1-7] [Compound 12]

[Intermediate 1-7] 9.53 mmol, 4.3 g and N- (4-fluorophenyl) dibenzo [b, d] furan-1-amine 22.8 mmol, using the same method as in 7) of Synthesis Example 1 Compound 12, 3.4 mmol, 3.2 g (yield 36%) was obtained. 3 shows an LC-Mass measurement graph of Compound 12.

Synthesis Example 6 Synthesis of Compound 13

       [Intermediate 1-7] [Compound 13]

Intermediate 1-7 The same procedure as in Synthesis Example 7) using 7.8 mmol, 3.5 g and 18.6 mmol of N- (4-fluorophenyl) dibenzo [b, d] furan-1-amine Compound 13, 2.5 mmol, 2.3 g (yield 32%) was obtained using the compound.

Synthesis Example 7 Synthesis of Compound 21

One)

      [Intermediate 1-3] [Intermediate 21-1]

[Intermediate 21-1] was synthesized by the same method as 7) for Synthesis Example 1) using [Intermediate 1-3] and (2-chloro-4,5-dimethylphenyl) boronic acid.

2)

        Intermediate 21-1] [Compound 21]

[Intermediate 21-1] Using Synthesis Example 1, 9.6 mmol, 4.6 g and 25.0 mmol, 2.9 g of 4-methyl-N- (m-tolyl)-[1,1'-biphenyl] -2-amine were used. Compound 21, 2.9 mmol, 2.8 g (yield 31%) was obtained using the same method as the same).

< Example >

Example  One

The glass substrate coated with ITO (indium tin oxide) having a thickness of 1300Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

The following compound [HI-A] was vacuum deposited to a thickness of 600 kPa on the prepared ITO transparent electrode to form a hole injection layer. The following compound [HAT-CN] (50 kPa) and the following compound [HT-B] (600 kPa) were sequentially vacuum deposited on the hole injection layer to form a hole transport layer. Next, the present invention provides a light emitting layer on the hole transport layer. [Compound 1] was doped at 2.5 wt% relative to [BH-A] and vacuum deposited to a film thickness of 200 kPa. In the formation of the electron transport layer on the light emitting layer configured as described above, 50 Å of [ET-A] was deposited and then 300 Å of vacuum was deposited at a 1: 1 ratio of [ET-B] and Liq. On the electron transport layer, lithium fluoride (LiF) and aluminum were deposited to a thickness of 1,000 Å in order to form a cathode.

/sec를 유지하였고, 음극의 리튬플루오라이드는 0.3 Å/sec, 알루미늄은 2 Å/sec증착 속도를 유지하였으며, 증착시 진공도는 1 Х 10^-7 내지 5 Х 10^-8 torr를 유지하여, 유기 발광 소자를 제작하였다. 소자의 수명은 유기 발광 소자를 10 mA/cm² 의 전류밀도에서 구동전압과 발광 효율을 측정하였고, 20 mA/cm² 의 전류밀도에서 초기 휘도 대비 90%가 되는 시간(T₉₀)을 측정하였다. 그 결과를 하기 표 1에 나타내었다.The deposition rate of organic material in the above process is 0.4 ~ 0.9

/ sec was maintained, the lithium fluoride of the cathode was 0.3 Å / sec, aluminum was 2 Å / sec deposition rate, the vacuum degree during deposition was maintained at 1 Х 10 ^-7 to 5 Х 10 ^-8 torr, organic A light emitting device was produced. The lifetime of the device was measured for the driving voltage and luminous efficiency of the organic light emitting device at a current density of 10 mA / cm ² , and a time (T ₉₀ ) of 90% of the initial luminance at a current density of 20 mA / cm ² . . The results are shown in Table 1 below.

             [HI-A] [Liq]

              [HT-B] [HAT-CN]

     [ET-A] [ET-B]

[BH-A] [BH-B] [BH-C]

[BD-A] [BD-B]

Example  2.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 2 instead of Compound 1.

Example  3.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 4 instead of Compound 1.

Example  4.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 7 instead of Compound 1.

Example  5.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 12 instead of Compound 1.

Example  6.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 13 instead of Compound 1.

Example  7.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 21 instead of Compound 1.

Example  8.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using [BH-B] instead of [BH-A].

Example  9.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using [BH-C] instead of [BH-A].

Example  10.

In Example 2, an organic light emitting diode was manufactured according to the same method as Example 2 except for using [BH-B] instead of [BH-A].

Example  11.

In Example 2, an organic light emitting diode was manufactured according to the same method as Example 2 except for using [BH-C] instead of [BH-A].

Example  12.

In Example 3, an organic light emitting diode was manufactured according to the same method as Example 3 except for using [BH-B] instead of [BH-A].

Example  13.

In Example 3, an organic light emitting diode was manufactured according to the same method as Example 3 except for using [BH-C] instead of [BH-A].

Example  14.

In Example 4, an organic light emitting diode was manufactured according to the same method as Example 4 except for using [BH-B] instead of [BH-A].

Example  15.

In Example 4, an organic light emitting diode was manufactured according to the same method as Example 4 except for using [BH-C] instead of [BH-A].

Example  16.

In Example 5, an organic light emitting diode was manufactured according to the same method as Example 5 except for using [BH-B] instead of [BH-A].

Example  17.

In Example 5, an organic light emitting diode was manufactured according to the same method as Example 5 except for using [BH-C] 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.

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.

Comparative example  3.

In Comparative Example 1, an organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using [BH-B] instead of [BH-A].

Comparative example  4.

In Comparative Example 2, an organic light emitting diode was manufactured according to the same method as Comparative Example 2 except for using [BH-B] instead of [BH-A].

Comparative example  5.

In Comparative Example 1, an organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using [BH-C] instead of [BH-A].

Comparative example  6.

In Comparative Example 2, an organic light emitting diode was manufactured according to the same method as Comparative Example 2 except for using [BH-C] instead of [BH-A].

Example Host Dopant @ 10 mA / cm ² @ 20 mA / cm ² Voltage (V) Efficiency (cd / A) CIE (x, y) Life span (T ₉₀ , hr) Example 1 [BH-A] Compound 1 3.5 9.2 (0.133, 0.138) 180 Example 2 [BH-A] Compound 2 3.5 8.9 (0.133, 0.142) 210 Example 3 [BH-A] Compound 4 3.6 9.0 (0.132, 0.144) 220 Example 4 [BH-A] Compound 7 3.4 9.3 (0.132, 0.142) 180 Example 5 [BH-A] Compound 12 3.5 9.2 (0.133, 0.140) 160 Example 6 [BH-A] Compound 13 3.5 9.3 (0.132, 0.143) 180 Example 7 [BH-A] Compound 21 3.6 9.2 (0.133, 0.144) 210 Example 8 [BH-B] Compound 1 3.3 8.5 (0.133, 0.138) 145 Example 9 [BH-C] Compound 1 3.7 8.6 (0.132, 0.138) 180 Example 10 [BH-B] Compound 2 3.4 8.3 (0.133, 0.142) 170 Example 11 [BH-C] Compound 2 3.8 8.9 (0.133, 0.143) 210 Example 12 [BH-B] Compound 4 3.4 8.4 (0.133, 0.144) 170 Example 13 [BH-C] Compound 4 3.3 8.5 (0.132, 0.144) 220 Example 14 [BH-B] Compound 7 3.3 8.4 (0.133, 0.142) 150 Example 15 [BH-C] Compound 7 3.6 9.2 (0.132, 0.142) 200 Example 16 [BH-B] Compound 12 3.3 8.2 (0.133, 0.141) 140 Example 17 [BH-C] Compound 12 3.7 9.0 (0.132, 0.143) 170 Comparative Example 1 [BH-A] [BD-A] 3.8 6.8 (0.132, 0.139) 85 Comparative Example 2 [BH-A] [BD-B] 3.6 6.5 (0.132, 0.138) 85 Comparative Example 3 [BH-B] [BD-A] 3.5 7.0 (0.132, 0.139) 75 Comparative Example 4 [BH-B] [BD-B] 3.7 6.5 (0.132, 0.138) 90 Comparative Example 5 [BH-C] [BD-A] 4.0 7.1 (0.132, 0.139) 95 Comparative Example 6 [BH-C] [BD-B] 4.2 6.7 (0.132, 0.138) 100

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 the organic light emitting device. The organic light emitting device using the same shows high efficiency and long life.

Examples 8 to 17 show the results of the combination experiments with the hosts of different characteristics, and showed excellent fluorescence properties even in the experiments with the 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)

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

In Chemical Formula 1,
X1 and X2 are the same as or different from each other, and each independently O, S, CRaRb or NRc,
Ra, Rb, Rc and R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted amine group; 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 Chemical Formula 2,
X1, X2, 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 groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted amine group; 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 Chemical Formulas 3 and 4,
X1, X2, 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 groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted amine group; 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 or different from each other. The method according to claim 3,
Ar21 to Ar24 are the same as or different from each other, and each independently represented by Formula 3-1 or 3-2:
[Formula 3-1]

[Formula 3-2]

In Chemical 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 CRd or N,
R, R ', R ", Rd, R8 and R9 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; 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 from 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 at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound according to any one of claims 1 to 5. Light emitting element. The method according to claim 6,
The organic material layer comprises a hole injection layer or a hole transport layer, the hole injection layer or hole transport layer is an organic light emitting device comprising the compound. The method according to claim 6,
The organic material layer comprises an electron transport layer or an electron injection layer, the electron transport layer or an electron injection layer is an organic light emitting device comprising the compound. The method according to claim 6,
The organic material layer comprises an emission layer, the emission layer comprises an organic light emitting device. The method according to claim 6,
The organic light emitting device comprises a light emitting layer and the light emitting layer comprises a compound represented by the following formula 1A:
[Formula 1A]

In Chemical Formula 1A,
L103 to L106 are the same as or different from each other, and each independently a direct bond; 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; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R 24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; 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, R 24 is the same as or different from each other. The method according to 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 according to 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 according to claim 6,
The organic material layer comprises an emission layer, the emission layer comprises an organic light emitting device comprising a compound represented by the following formula (1B):
[Formula 1B]

In Chemical Formula 1B,
L107 to L109 are the same as or different from each other, and each independently a direct bond; 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; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R 25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; 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, R 25 is the same as or different from each other. The method according to 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 according to 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:

.

Images