KR20200016498A - Polycyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound represented by chemical formula 1 and an organic light emitting device comprising the same. The organic light emitting device of the present specification includes: a first electrode; a second electrode; and a compound wherein at least one layer of an organic material layers has been described.

Description

POLYCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME

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

In the present specification, an organic light emitting device is a light emitting device using an organic semiconductor material and requires an exchange of holes and / or electrons between an electrode and an organic semiconductor material. 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 layer is often composed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer, etc. Can lose. 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 suppressing materials, electron transport materials, electron injection materials and the like depending on their functions. The light emitting materials include blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize better natural colors, depending on the light emission color.

In addition, a host / dopant system may be used as the light emitting material in order to increase luminous efficiency through an 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 a 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 which constitutes an organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron suppressor material, an electron transport material, an electron injection material, etc., is stable and efficient. Backed by, the development of new materials continues to be required.

International Patent Publication No. 2017-126443

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

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

[Formula 1]

In Chemical Formula 1,

R11 to R14 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

A1, A2, B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,

L1 to L3 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,

R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,

n1 and n2 are each 0 or 1, n1 + n2 is 1,

m1 is an integer of 0 to 8, m2 is an integer of 0 to 7, m3 is an integer of 0 to 9, and when m1 to m3 are each an integer of 2 or more, the substituents in the two or more parentheses are the same as or different from each other.

In addition, the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the aforementioned compound.

The compound described herein can be used as the material of the organic material layer of the organic light emitting device.

When the organic light emitting device including the compound according to the exemplary embodiment of the present specification is manufactured, an organic light emitting device having excellent luminous efficiency, low driving voltage, high efficiency, and long life may be obtained.

1 illustrates a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a hole control layer 105, a light emitting layer 106, an electron control layer 107, and an electron transport layer 108. , An example of an organic light emitting device including an electron injection layer 109 and a cathode 110 is illustrated.

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

The present specification provides a compound represented by the following Formula 1. The compound represented by the following formula (1) includes one spiro structure in anthracene, and when applied to an organic light emitting device, it is possible to drive a low voltage, excellent in power efficiency, and excellent in light emission characteristics such as brightness and luminous efficiency. In addition, since the compound of the present invention has an appropriate molecular weight, it has thermal stability in the deposition process of the organic light emitting device.

[Formula 1]

In Chemical Formula 1,

R11 to R14 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

A1, A2, B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,

L1 to L3 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,

R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,

n1 and n2 are each 0 or 1, n1 + n2 is 1,

m1 is an integer of 0 to 8, m2 is an integer of 0 to 7, m3 is an integer of 0 to 9, and when m1 to m3 are each an integer of 2 or more, the substituents in the two or more parentheses are the same as or different from each other.

According to an exemplary embodiment of the present invention, the compound represented by Chemical Formula 1 may be used as a blue host in the emission layer. Currently, phosphorescent materials are commonly used as compounds used in organic light emitting devices, and phosphorescent devices using iridium (Ir) complexes have been actively studied. Efforts have been made to introduce phosphors in the blue emission region as well as red and green, but due to the high singlet energy of the blue host, the relationship between chemical structural stability and bond dissociation energy (BDE) And low levels due to exciton generating regions in the light emitting layer. Blue hosts are generally synthesized on the basis of high bandgap energies of 3.0 eV or more and are stagnant in the application of anthracene derivatives. The present invention proposes a compound combining anthracene and a new spiro structure to provide an organic light emitting device having excellent device properties.

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 one 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 substituted, that is, a position where the substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" is deuterium (-D); Halogen group; Cyano group (-CN); Nitro group; Hydroxyl group; Silyl groups; Boron group; Alkyl groups; An alkoxy group; Alkenyl groups; Alkynyl groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Cycloalkyl group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a 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 terphenyl group. That is, the terphenyl group may be an aryl group or may be interpreted as a substituent to which three 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 the formula of -SiY _a Y _b Y _c , wherein Y _a , Y _b and Y _c are each hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. 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; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group. The boron group may include, but is not limited to, trimethylboron group, triethylboron group, tert-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 methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group and the like, but are not limited thereto.

In this specification, although carbon number of the said alkoxy group is not specifically limited, It is preferable that it is 1-60. According to an exemplary embodiment, the alkoxy group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 10 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, methoxy group, ethoxy group, propoxy group, butoxy group, 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 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, a quarterphenyl group, or the like, 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, triphenylenyl group, etc., but is not limited thereto. no.

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

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

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

,

Spirofluorenyl groups such as

(9,9-dimethylfluorenyl group), and

Substituted fluorenyl groups such as (9,9-diphenylfluorenyl 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, S, and Se as hetero atoms, and the 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, pyridyl group, pyrrole group, pyrimidyl group, quinolinyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothio Phenyl group, carbazolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiophenyl group, indenocarbazolyl group and the like, but are 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, in the substituted or unsubstituted ring formed by bonding to each other, the “ring” is a hydrocarbon ring; Or heterocycle.

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.

Description of the heterocyclic group can be applied except that the heterocyclic ring is divalent.

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

In the present specification, the description about the heteroaryl group described above may be applied except that the heteroarylene group is a divalent group.

According to an exemplary embodiment of the present specification, n1 and n2 are each 0 or 1, and n1 + n2 is 1.

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

[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,

L1 to L3, R1 to R3, R11 to R14, m1 to m3, A1, A2, B1 and B2 are the same as defined in Chemical Formula 1.

According to an exemplary embodiment of the present specification, A1, A2, B1 and B2 are the same as or different from each other, and each independently substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 60 carbon atoms.

In another exemplary embodiment, A1, A2, B1, and B2 are the same as or different from each other, and each independently substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 30 carbon atoms.

According to another exemplary embodiment, A1, A2, B1, and B2 are the same as or different from each other, and each independently a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or having 1 to 20 carbon atoms. An aromatic hydrocarbon ring having 6 to 30 carbon atoms unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms, unsubstituted or substituted with an alkyl group; Or an aromatic heterocarbon having 2 to 30 carbon atoms unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms. It is a ring.

In another exemplary embodiment, A1, A2, B1, and B2 are the same as or different from each other, and are each independently substituted or unsubstituted with a methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, or tert-butyl group. C6-C30 aromatic hydrocarbon ring unsubstituted or substituted with a phenyl group; Or an aromatic heterocyclic ring having 2 to 30 carbon atoms unsubstituted or substituted with a phenyl group unsubstituted or substituted with a methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, or tert-butyl group.

In another exemplary embodiment, A1, A2, B1, and B2 are the same as or different from each other, and are each independently a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or having 1 to 20 carbon atoms. Benzene unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group; Naphthalene unsubstituted or substituted with a C6-C30 aryl group unsubstituted or substituted with a C1-C20 trialkylsilyl group, a C1-C20 alkyl group, or a C1-C20 alkyl group; Phenanthrene unsubstituted or substituted with a C6-C30 aryl group unsubstituted or substituted with a C1-C20 trialkylsilyl group, a C1-C20 alkyl group, or a C1-C20 alkyl group; Triphenylene unsubstituted or substituted with a C6-C30 aryl group unsubstituted or substituted with a C1-C20 trialkylsilyl group, a C1-C20 alkyl group, or a C1-C20 alkyl group; Fluorene unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms; Dibenzofuran unsubstituted or substituted with a C6-C30 aryl group unsubstituted or substituted with a C1-C20 trialkylsilyl group, a C1-C20 alkyl group, or a C1-C20 alkyl group; Or dibenzothiophene unsubstituted or substituted with a C6-C30 aryl group unsubstituted or substituted with a C1-C20 trialkylsilyl group, a C1-C20 alkyl group, or a C1-C20 alkyl group.

According to another exemplary embodiment, A1, A2, B1, and B2 are the same as or different from each other, and are each independently substituted or unsubstituted with a methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, or tert-butyl group. Benzene unsubstituted or substituted with a substituted phenyl group; Naphthalene unsubstituted or substituted with a phenyl group unsubstituted or substituted with a methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, or tert-butyl group; Phenanthrene with a phenyl group unsubstituted or substituted with a methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, or tert-butyl group; Triphenylene with a phenyl group unsubstituted or substituted with a methyl group, isopropyl group, trimethylsilyl group, or tert-butyl group; Fluorene unsubstituted or substituted with a methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, or tert-butyl group; Dibenzofuran with a phenyl group unsubstituted or substituted with a methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, or tert-butyl group; Or dibenzothiophene unsubstituted or substituted with a phenyl group unsubstituted or substituted with a methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, or tert-butyl group.

According to an exemplary embodiment of the present specification, the R11 to R14 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, R11 to R14 are the same as or different from each other, and each independently hydrogen; Methyl group; Ethyl group; Or a phenyl group.

According to an exemplary embodiment of the present specification, the L1 to L3 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.

According to another exemplary embodiment, the L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L1 to L3 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 heteroarylene group containing O, S, or N as a substituted or unsubstituted hetero atom having 2 to 60 carbon atoms.

According to another exemplary embodiment, the L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Substituted or unsubstituted naphthylene group; A substituted or unsubstituted fluorenylene group; Substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted dibenzothiophenylene group.

In another exemplary embodiment, L1 to L3 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Naphthylene group; Fluorenylene groups substituted with methyl groups; Dibenzofuranylene group; Or a dibenzothiophenylene group.

According to an exemplary embodiment of the present specification, the R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; Substituted or unsubstituted C2-C30 alkynyl group; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; Substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; Substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms; Substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 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, or combine with an adjacent group to form a substituted or unsubstituted ring having 2 to 60 carbon atoms.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted trialkylsilyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; Substituted or unsubstituted isopropyl group; A substituted or unsubstituted tert-butyl group; Substituted or unsubstituted trimethylsilyl group; Or a substituted or unsubstituted phenyl group.

According to another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Isopropyl group; tert-butyl group; Trimethylsilyl group; Or a phenyl group.

According to an exemplary embodiment of the present specification, m1 is an integer of 0 to 2, when m1 is 2, two R1 are the same as or different from each other.

According to an exemplary embodiment of the present specification, m2 is an integer of 0 to 2, when m2 is 2, two R2 are the same as or different from each other.

According to an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; 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, R3 is hydrogen; heavy hydrogen; An aryl group having 6 to 60 carbon atoms unsubstituted or substituted with deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or a C2-C60 heterocyclic group unsubstituted or substituted with deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, R3 is hydrogen; heavy hydrogen; Phenyl group unsubstituted or substituted with deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A terphenyl group unsubstituted or substituted with deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A naphthyl group unsubstituted or substituted with deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Fluorenyl group unsubstituted or substituted with deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Benzofluorenyl group unsubstituted or substituted with deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Phenanthrenyl groups unsubstituted or substituted with deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A dibenzofuranyl group unsubstituted or substituted with deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A dibenzothiophenyl group unsubstituted or substituted with deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Carbazolyl unsubstituted or substituted with deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Naphthobenzothiophenyl group unsubstituted or substituted with deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or a naphthobenzofuranyl group unsubstituted or substituted with deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, m3 is an integer of 0 to 3, when m2 is 2 or more, two or more '-L3-R3' are the same as or different from each other.

In one embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 4.

[Formula 4]

In Chemical Formula 4,

R1, R2, R11 to R14, m1, m2, A1, A2, B1, B2, n1, n2, L1 and L2 are the same as defined in Formula 1,

L4 and L5 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,

R4 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,

Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

m4 is an integer of 0 to 8, and when m4 is 2 or more, the substituents in the two or more parentheses are the same as or different from each other,

m5 is an integer of 0 to 3, and when m5 is 2 or more, two or more L5s are the same or different from each other.

According to an exemplary embodiment of the present specification, L4 is 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.

According to one embodiment, the L4 is a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L4 is a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a heteroarylene group containing O, S, or N as a substituted or unsubstituted hetero atom having 2 to 60 carbon atoms.

According to one embodiment, the L4 is a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Substituted or unsubstituted naphthylene group; A substituted or unsubstituted fluorenylene group; Substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted dibenzothiophenylene group.

In another exemplary embodiment, L4 is a direct bond; Phenylene group; Biphenylene group; Naphthylene group; Fluorenylene groups substituted with methyl groups; Dibenzofuranylene group; Or a dibenzothiophenylene group.

According to an exemplary embodiment of the present specification, R4 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, R4 is hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.

In another exemplary embodiment, R4 is hydrogen; heavy hydrogen; Methyl group; Or a phenyl group.

In one embodiment of the present specification, m4 is an integer of 0 to 2, when m4 is 2, the two '-L4-R4' are the same as or different from each other.

In one embodiment of the present specification, m5 is an integer of 0 to 2, and when m5 is 2, two L5 are the same as or different from each other.

According to an exemplary embodiment of the present disclosure, the L5 is 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.

According to one embodiment, the L5 is a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L5 is a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a heteroarylene group containing O, S, or N as a substituted or unsubstituted hetero atom having 2 to 60 carbon atoms.

According to one embodiment, the L5 is a direct bond; Substituted or unsubstituted phenylene group; Or substituted or unsubstituted naphthylene.

In another exemplary embodiment, L5 is a direct bond; Phenylene group; Or naphthylene.

According to an exemplary embodiment of the present specification, Ar1 is a 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, Ar1 is a 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, Ar1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted benzofluorenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted naphthobenzofuranyl group; Or a substituted or unsubstituted naphthobenzothiophenyl group.

According to another exemplary embodiment, Ar1 is a phenyl group unsubstituted or substituted with deuterium, a methyl group, a tert-butyl group, or a trimethylsilyl group; A biphenyl group unsubstituted or substituted with deuterium, tert-butyl group or trimethylsilyl group; Terphenyl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group; Benzofluorenyl group substituted with a methyl group; Phenanthrenyl group; Dibenzofuranyl group; Dibenzothiophenyl group; Carbazole groups substituted with phenyl groups; Naphthobenzofuranyl group; Or a naphthobenzothiophenyl group.

According to an exemplary embodiment of the present invention, Formula 1 may be represented by any one of the following compounds.

In one embodiment of the present specification, the bandgap energy of the compound represented by Formula 1 is 3.0 eV or more and 4.0 eV or less, the bandgap energy range is satisfied and the compound represented by Formula 1 is used as a host of the light emitting layer. In this case, since the energy transition to the dopant is smoothly performed, an element having excellent luminous efficiency can be obtained.

The band gap energy (E _bg ) can be obtained by measuring the LUMO energy and HOMO energy of the molecule.

To determine the distribution of electrons and the optical properties in the molecule, a determined structure is required. In addition, the electronic structure has different structures in the neutral, anion and cation states depending on the charge state of the molecule. The energy level of neutral state, cation and anion state is all important for driving the device, but typically, the highest occupied molecular orbital (HOMO) and the lower unoccupied molecular orbital (LUMO) are recognized as important physical properties.

In order to determine the molecular structure of a chemical, we use density functional theory to optimize the structure entered. The BPW91 calculation method (Becke exchange and perdew correlation-correlation functional) and the DNP (double numerical basis set including polarization functional) basis set are used for the DFT calculation. BPW91 calculations are described in the paper A. D. Becke, Phys. Rev. A, 38, 3098 (1988) and 'J. P. Perdew and Y. Wang, Phys. Rev. B, 45, 13244 (1992), and the DNP base set is the paper 'B. Delley, J. Chem. Phys., 92, 508 (1990).

Biovia's “DMol3” package can be used to perform calculations using the density function method. Determining the optimal molecular structure using the method given above gives the resultant energy level that the electron can occupy. HOMO energy refers to the highest energy orbital energy among the electron-filled molecular orbitals when the neutral state energy is obtained, and LUMO energy corresponds to the lowest energy orbital energy among the molecular orbitals without electrons.

In addition, the energy level of the singlet and triplet is calculated using a time dependent density functional theory (TD-DFT) to obtain the excited properties of the optimal molecular structure determined by the above method. The calculation of the density function can be performed using the 'Gaussian09' package, a commercial calculation program developed by Gaussian. The B3PW91 calculation (Becke exchange and Perdew correlation-correlation functional) and the 6-31G * basis set are used to calculate the time dependent density function. The base set for 6-31G * is the paper 'J. A. Pople et al., J. Chem. Phys. 56, 2257 (1972).

For the optimal molecular structure determined using the full density function method, the energy of the electron arrays in single and triplet is calculated using the time dependent density function method (TD-DFT).

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 may be prepared by the following Scheme 1. Substituents may be combined by methods known in the art, and the type, position, and number of substituents may be changed according to techniques known in the art.

<Scheme 1>

In Scheme 1, the definition of a substituent is the same as in Chemical Formula 1 above, X means a halogen group, or sulfonyl group.

In the present specification, compounds having various energy band gaps may be synthesized by introducing various substituents into the core structure of Chemical Formula 1. In addition, in the present specification, the HOMO and LUMO energy levels of the compound may also be adjusted 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 satisfying the requirements of the organic layer by introducing a substituent mainly used in the hole injection layer material, hole transport material, electron suppression material, light emitting layer material and electron transport layer material used in manufacturing the organic light emitting device to the core structure. The substance to make can be synthesize | combined.

In addition, the organic light emitting device according to the present specification 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 a compound represented by Chemical Formula 1 described above.

The organic light emitting device of the present specification 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 represented by Chemical Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in manufacturing an 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 specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention includes a hole injection layer, a hole control layer, a hole transport layer, a hole transport layer, a hole transport and hole injection at the same time, an electron control layer, an electron suppression layer, a light emitting layer, an electron transport layer and an electron injection layer, electrons It may have a structure including a layer for transport and electron injection at the same time. However, the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.

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

In the organic light emitting device of the present specification, the organic material layer may include a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer may include the aforementioned compound.

In the organic light emitting device of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer includes the aforementioned compound.

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.

In 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, and further include a dopant. In this case, the dopant of the light emitting layer may be included in an amount of 0.1 parts by weight or more and 10 parts by weight or less with respect to 100 parts by weight of the host, preferably 0.5 parts by weight or more and 5 parts by weight or less.

In another exemplary embodiment, the organic material layer includes a light emitting layer, the light emitting layer includes one compound as a host of the light emitting layer, and the one compound may be the compound described above.

According to another exemplary embodiment, the organic material layer may include a light emitting layer, the light emitting layer may include two or more compounds as a host of the light emitting layer, and the two or more compounds may be the aforementioned compounds.

According to an exemplary embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer may include one kind (single species) or two or more kinds of compounds as a host of the emitting layer, and the two or more kinds of compounds may be the aforementioned compounds. And it may include a compound represented by the formula (X). In this case, the weight ratio of the compound represented by Formula 1 and the compound represented by Formula X (weight of Formula 1: weight of Formula X) may be 1:10 to 10: 1.

[Formula X]

In Chemical Formula X,

Y1 to Y10 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present invention, Y1 to Y10 are the same as or different from each other, and each independently hydrogen; 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 heteroaryl group having 2 to 30 carbon atoms.

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

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.

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

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.

For example, the organic light emitting diode may have a laminate 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 / light emitting layer / layer / electrode simultaneously injecting and transporting electrons

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

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

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

1 shows an anode 102, a hole injection layer 103, a hole transport layer 104, a hole control layer 105, a light emitting layer 106, an electron control layer 107, and an electron transport layer 108 on a substrate 101. The structure of the organic light emitting device in which the electron injection layer 109 and the cathode 110 are sequentially stacked is illustrated. In such a structure, the compound may be included in the emission layer 106.

For example, the organic light emitting device according to the present invention uses a metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to form a metal oxide or a metal oxide or an alloy thereof on a substrate. To form an anode by depositing an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon. Can be. 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 is a hole injection layer, a hole transport layer, a hole control layer, a layer for simultaneously injecting and transporting electrons, an electron control layer, an electron suppression layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron injection and electron transport at the same time It may be a multi-layer structure including, but not limited to, it may be 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, 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 hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic materials, 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 in that the hole injection characteristic is prevented from being lowered. When the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is too thick, so 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 the hole buffer layer 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 suppression layer may be a compound described above or a material known in the art.

The hole control layer may include a carbazole compound, an amine compound, and the like, but is not limited thereto.

The electron control layer may include a triazine compound and the like, but is not limited thereto.

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 receiving and combining holes and electrons from the hole transporting layer and the electron transporting 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-hydroxybenzo quinoline-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, there exist a condensed aromatic ring derivative, a heterocyclic containing compound, etc. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and 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 ), Phosphors such as octaethylporphyrin platinum (PtOEP), or fluorescent materials such as Alq ₃ (tris (8-hydroxyquinolino) aluminum) may be used, but are 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.

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 of transporting 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 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-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.

The hole suppression 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, 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.

< Production Example >

Production Example  1 (Step 1-1 or Step 2-1)

Step 1-1 and Step 2- 1 of  synthesis

After dissolving SM1 (1eq) in tetrahydrofuran (THF) (excess), the temperature was lowered to -7 ° C, and then 2.5M n-BuLi (1.5eq) was added dropwise and SM2 (1.05eq) described in Table 1 below. To put and raise to room temperature (RT) and stirred for 1 hour. 1N HCl (excess) was added thereto, stirred for 30 minutes, layers were separated, solvents were removed, the residue was purified by ethyl acetate, and the obtained solid was added to acetic acid (excess). Then, 1 ml of sulfuric acid was added dropwise and refluxed. After the temperature was lowered to room temperature and neutralized with water, the filtered solid was recrystallized from tetrahydrofuran and ethyl acetate to prepare A1-1 to A1-12 shown in Table 1 below. In the above preparation, R ₁₀₁ to R ₁₀₄ each represent a substituent, and a, b, c, and d each represent the number of substituents.

Step 1-1 or Step 2-1 Intermediate SM1 SM2 Pruduct yield ( % ) MS [M + H] ⁺ A1-1

75% 410.33 A1-2

73% 410.33 A1-3

68% 410.33 A1-4

70% 460.39 A1-5

71% 460.39 A1-6

76% 466.43 A1-7

77% 516.47 A1-8

75% 500.41 A1-9

78% 410.33 A1-10

74% 410.33 A1-11

81% 410.33 A1-12

79% 460.39

Production Example  2 (Step 1-2 or Step 2-2)

Step 1-2 and Step 2- 2 of  synthesis

Under nitrogen, A1-1 to A1-12 (1eq) synthesized in Preparation Example 1 and alkyl iodide to phenyl iodide (3.5eq, SM2) described in Table 2 were added thereto, and room temperature stirring was performed for 12 hours. . After completion of the reaction, methanol was added and filtered. The solid was extracted with chloroform and distilled water and concentrated to separate the column (EA: Hex = 1: 25) to prepare B1-1 to B1-14 in Table 2 below. In the above preparation, R ₁₀₁ to R ₁₀₄ , R ′, and R ″ each represent a substituent, and a, b, c, and d each represent the number of substituents.

Step 1-2 or Step 2-2 Intermediate SM1 SM2 Pruduct yield ( % ) MS [M + H] ⁺ B1-1 A1-1 CH ₃ I

70% 438.38 B1-2 A1-1

71% 562.52 B1-3 A1-2 CH ₃ I

68% 438.38 B1-4 A1-2

65% 466.43 B1-5 A1-3 CH ₃ I

72% 438.38 B1-6 A1-4 CH ₃ I

71% 488.44 B1-7 A1-5 CH ₃ I

68% 488.44 B1-8 A1-6 CH ₃ I

66% 494.49 B1-9 A1-7 CH ₃ I

69% 516.47 B1-10 A1-8 CH ₃ I

75% 528.46 B1-11 A1-9 CH ₃ I

72% 438.38 B1-12 A1-10 CH ₃ I

63% 438.38 B1-13 A1-11 CH ₃ I

438.38 438.38 B1-14 A1-12 CH ₃ I

64% 488.44

Production Example  3 (Step 1-3 or Step 2-3)

Step 1-3 and Step 2- 3 of  synthesis

After dissolving one of B1-5, B1-12, and B1-13 (1eq) in tetrahydrofuran (THF, excess), the temperature was lowered to -78 ° C, and 2.5M n-BuLi (1.5eq) was added dropwise thereto. After minutes, SM2 (1.3eq) described in Table 3 was added thereto, and after raising to room temperature, the mixture was stirred for 1 hour. 1N HCl (excess) was added thereto, stirred for 30 minutes, and the layers were separated, the solvent was removed, the residue was purified by ethyl acetate, and the obtained solid was added to acetic acid (excess). After the temperature was lowered to room temperature and neutralized with water, the filtered solid was recrystallized from tetrahydrofuran and ethyl acetate to prepare C1-1 to C1-3 of Table 3 below. In the above preparation, R ₁₀₁ to R ₁₀₄ , R ′, and R ″ each represent a substituent, and a, b, c, and d each represent the number of substituents.

Step 1-3 or Step 2-3 Intermediate SM1 SM2 Pruduct yield ( % ) MS [M + H] ⁺ C1-1 B1-5

92% 403.30 C1-2 B1-12

95% 403.30 C1-3 B1-13

93% 403.30

Production Example  4 (Step 1-4 or Step 2-4)

Step 1-4 and Step 2- 4 of  synthesis

One of C1-1 to C1-3 (1eq) and SM2 (1.05eq) described in Table 4 below were added to tetrahydrofuran (excess), and then 2M potassium carbonate aqueous solution (30 vol. Ratio to THF) was added thereto. Keystriphenyl-phosphinopalladium (2 mol%) was added thereto, followed by heating and stirring for 10 hours. After the temperature was lowered to room temperature and the reaction was terminated, the aqueous solution of potassium carbonate was removed to separate the layers. Vacuum distillation after removing the solvent to prepare C2-1 to C2-4 of Table 4. In the above preparation, R ₁₀₁ to R ₁₀₄ , R ′ and R ″ each represent a substituent, L ₁ and L ₂ each represent a linking group, and a, b, c and d each represent the number of substituents.

Step 1-4 or Step 2-4 Intermediate SM1 SM2 Pruduct yield ( % ) MS [M + H] ⁺ C2-1 C1-1

92% 527.68 C2-2 C1-2

89% 451.58 C2-3 C1-1

85% 501.64 C2-4 C1-3

86% 501.64

Production Example  5 (Step 1-5 or Step 2-5)

Step 1-5 and Step 2- 5 of  synthesis

After dissolving one of C2-1 to C2-4 (1eq) by adding to chloroform (excess), perfluorobutanesulfonyl fluoride (2.5eq, SM2) was slowly added dropwise at room temperature and stirred at room temperature for 3 hours. It was. Extracted with water and chloroform (chloroform) at room temperature and concentrated to give C3-1 to C3-4 of Table 5 which is a white solid with hexane. In the above preparation, R ₁₀₁ to R ₁₀₄ , R ′ and R ″ each represent a substituent, L ₁ and L ₂ each represent a linking group, and a, b, c and d each represent the number of substituents, X means a sulfonyl group.

Step 1-5 or Step 2-5 Intermediate SM1 SM2 Pruduct yield ( % ) MS [M + H] ⁺ C3-1 C2-1

92% 809.77 C3-2 C2-2

89% 733.66 C3-3 C2-3

85% 783.72 C3-4 C2-4

86% 783.72

Production Example  6 (compound 1 to compound 20 of  synthesis)

Step 1-6 and Step 2- 6 of  synthesis

Tetrahydrofuran (excess) between one of B1-1 to B1-14, C3-1 to C3-4, B1-2, A1-1 and B1-4 (1eq) and SM2 (1.03eq) described in Table 6 below After addition to 2M aqueous potassium carbonate solution (30% by volume compared to THF) was added, tetrakistriphenyl-phosphinopalladium (2mol%) was added, and then stirred for 10 hours by heating. After the temperature was lowered to room temperature and the reaction was terminated, the aqueous solution of potassium carbonate was removed to separate the layers. After removing the solvent to recrystallized with tetrahydrofuran and ethyl acetate to give the compound 1 to 20 of Table 6. In the above preparation, R ₁₀₁ to R ₁₀₄ , R ′ and R ″ each represent a substituent, L ₁ and L ₂ each represent a linking group, and a, b, c and d each represent the number of substituents, X means a sulfonyl group.

Step 1-6 or Step 2-6 composite SM1 SM2 Pruduct yield ( % ) MS [M + H] ⁺ Compound 1 B1-1

72% 611.8 Compound 2 B1-1

63% 727.96 Compound 3 B1-3

66% 737.96 Compound 4 B1-5

69% 711.92 Compound 5 B1-8

66% 667.91 Compound6 B1-11

67% 687.9 Compound 7 B1-12

65% 777.98 Compound 8 B1-12

75% 639.85 Compound 9 B1-7

72% 689.91 Compound 10 B1-9

71% 722.97 Compound 11 B1-6

70% 737.96 Compound 12 B1-10

73% 777.98 Compound 13 B1-14

69% 711.92 Compound 14 C3-1

65% 764 Compound 15 C3-2

66% 687.9 Compound 16 C3-3

68% 767.96 Compound 17 C3-4

72% 810.14 Compound 18 B1-2

71% 735.94 Compound 19 A1-1

64% 664.87 Compound 20 B1-4

70% 689.91

< Example Of Comparative example >

< Example  1> OLED  Manufacture

The substrate on which 70/1000/70 mm deposited ITO / Ag / ITO was deposited as a positive electrode was cut into a size of 50 mm x 50 mm x 0.5 mm, and the dispersant was put in distilled water and washed with ultrasonic waves. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.

H-1 was thermally vacuum deposited to a thickness of 50 kPa on the anode thus prepared to form a hole injection layer, and HT1, which is a material for transporting holes, was vacuum deposited to 1150 kPa to form a hole transport layer. Next, a hole control layer was formed using HT2 (150 kPa), and then the host compound 1 and dopant BD1 (2 wt%) synthesized in Preparation Example 6 were vacuum deposited to a thickness of 360 kPa to form a light emitting layer. Thereafter, ET1 was deposited at 50 kPa to form an electron control layer, and compound ET2 and Liq were mixed at 7: 3 to form an electron transport layer having a thickness of 250 kPa. 50 μm thick magnesium and lithium fluoride (LiF) were sequentially formed into an electron injection layer <EIL>, and 200 μm of magnesium and silver (1: 4) were formed as a cathode, and 600 μm of CP1 was deposited to complete the device. In the above process, the deposition rate of the organic material was maintained at 1 Å / sec. The experimental results of the organic light emitting device of Example 1 are shown in Table 7 below.

<Examples 2 to 21 and Comparative Examples 1 to 3> Preparation of OLED

Examples 2 to 20 prepared in the same manner as in Example 1 except for using Compounds 1 to 20 synthesized in Preparation Example 6 as a host material of the light emitting layer and BD1 or BD2 as a dopant material of the light emitting layer, respectively. 21 and the experimental results of the organic light emitting device of Comparative Examples 1 to 3 are shown in Table 7. In Table 7, the life is measured at 95% of the initial luminance at a current density of 20 mA / cm ² .

Experimental Example
20 mA / ㎠ Host Dopant Voltage (V)
(@ 20mA / cm ² ) Cd / A
(@ 20mA / cm ² ) Color coordinates
(x, y) life span
(T95, h)
(@ 20mA / cm ² ) Example 1 Compound 1 BD1 3.51 6.71 (0.135, 0.138) 49.0 Example 2 Compound 2 BD1 3.45 6.63 (0.134, 0.137) 50.2 Example 3 Compound 3 BD1 3.41 6.58 (0.135, 0.138) 55.2 Example 4 Compound 5 BD1 3.34 6.82 (0.134, 0.138) 51.2 Example 5 Compound 6 BD1 3.42 6.72 (0.136, 0.139) 48.9 Example 6 Compound 8 BD1 3.31 6.52 (0.135, 0.138) 48.5 Example 7 Compound 10 BD1 3.50 6.69 (0.133, 0.139) 49.1 Example 8 Compound 11 BD1 3.56 6.78 (0.135, 0.138) 50.2 Example 9 Compound 12 BD1 3.48 6.58 (0.134, 0.138) 50.1 Example 10 Compound 13 BD1 3.50 6.67 (0.136, 0.139) 55.0 Example 11 Compound 14 BD1 3.51 6.77 (0.136, 0.139) 53.5 Example 12 Compound 16 BD1 3.42 6.72 (0.135, 0.138) 48.9 Example 13 Compound 18 BD1 3.31 6.52 (0.135, 0.138) 48.5 Example 14 Compound 19 BD1 3.50 6.69 (0.133, 0.139) 49.1 Example 15 Compound 20 BD1 3.48 6.71 (0.134, 0.139) 51.1 Example 16 Compound 1 BD2 3.51 7.01 (0.135, 0.122) 40.2 Example 17 Compound 7 BD2 3.52 7.13 (0.134, 0.121) 43.2 Example 18 Compound 9 BD2 3.55 7.08 (0.136, 0.123) 41.5 Example 19 Compound 12 BD2 3.55 7.12 (0.136, 0.120) 42.5 Example 20 Compound 15 BD2 3.54 7.18 (0.133, 0.121) 44.1 Example 21 Compound 17 BD2 3.42 7.11 (0.134, 0.122) 41.0 Comparative Example 1 BH1 BD1 4.01 5.12 (0.136, 0.139) 38.0 Comparative Example 2 BH1 BD2 4.12 6.50 (0.135, 0.122) 20.2 Comparative Example 3 BH2 BD1 4.10 5.23 (0.135, 0.122) 35.2

The organic light emitting device including the compound of the formula according to the present invention uses the compound of the present invention prepared in Preparation Example 6 as a host of the blue organic light emitting device, through the balance of holes and electrons of the organic light emitting device according to the chemical structure The device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage and stability.

< Example  22> OLED  Manufacture

The substrate on which 70/1000/70 mm deposited ITO / Ag / ITO was deposited as a positive electrode was cut into a size of 50 mm x 50 mm x 0.5 mm, and the dispersant was put in distilled water and washed with ultrasonic waves. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.

H-1 was thermally vacuum deposited to a thickness of 50 kPa on the anode thus prepared to form a hole injection layer, and HT1, which is a material for transporting holes, was vacuum deposited to 1150 kPa to form a hole transport layer. Next, the hole control layer was formed using HT2 (150 kPa), and then Compound 1 and BH1 synthesized in Preparation Example 6 were co-deposited with dopant BD1 (2% by weight) at a weight ratio of 50:50. To form a light emitting layer with a thickness of 360 kPa. Thereafter, ET1 was deposited at 50 kPa to form an electron control layer, and compound ET2 and Liq were mixed at 7: 3 to form an electron transport layer having a thickness of 250 kPa. 50 μm thick magnesium and lithium fluoride (LiF) were sequentially formed into an electron injection layer <EIL>, and 200 μm of magnesium and silver (1: 4) were formed as a cathode, and 600 μm of CP1 was deposited to complete the device. In the above process, the deposition rate of the organic material was maintained at 1 Å / sec. The experimental results of the organic light emitting device of Example 22 are shown in Table 8 below.

< Example  23 to 36 and Comparative example  4 to 8 OLED  Manufacture

Example 22 prepared in the same manner as in Example 22, except for using Compounds 1 to 20 synthesized in Preparation Example 6 as materials for the mixed host of the light emitting layer and BD1 or BD2 as the dopant material for the light emitting layer. Experimental results of the organic light emitting diodes of Examples 36 to 8 and Comparative Examples 4 to 8 are shown in Table 8 below. In Table 8, the life is measured at 95% of the initial luminance at a current density of 20 mA / cm ² .

Experimental Example
20 mA / ㎠ Host (weight ratio) Dopant   Voltage (V)
(@ 20mA / cm ² ) Cd / A
(@ 20mA / cm ² ) Color coordinates
(x, y) life span
(T95, h)
(@ 20mA / cm ² ) Example 22 Compound 1: BH1 (5: 5) BD1 3.51 6.55 (0.135, 0.138) 49.0 Example 23 Compound 10: BH1 (5: 5) BD1 3.45 6.68 (0.134, 0.137) 50.2 Example 24 Compound 13: BH1 (7: 3) BD1 3.41 6.88 (0.135, 0.138) 55.2 Example 25 Compound 3: BH2 (5: 5) BD1 3.34 6.52 (0.134, 0.138) 51.2 Example 26 Compound 12: BH2 (5: 5) BD1 3.42 6.33 (0.136, 0.139) 48.9 Example 27 Compound 20: BH2 (3: 7) BD1 3.31 6.45 (0.135, 0.138) 48.5 Example 28 Compound 8: Compound 17 (5: 5) BD1 3.50 6.69 (0.133, 0.139) 49.1 Example 29 Compound 11: Compound 19 (5: 5) BD1 3.56 6.78 (0.135, 0.138) 50.2 Example 30 Compound 2: Compound 7 (5: 5) BD1 3.48 6.58 (0.134, 0.138) 50.1 Example 31 Compound 4: Compound 9 (3: 7) BD1 3.50 6.67 (0.136, 0.139) 55.0 Example 32 Compound 2: Compound 12 (7: 3) BD1 3.51 6.77 (0.136, 0.139) 53.5 Example 33 Compound 1: Compound 11 (5: 5) BD2 3.54 7.05 (0.136, 0.123) 43.2 Example 34 Compound 2: Compound 19 (5: 5) BD2 3.61 7.02 (0.136, 0.120) 44.5 Example 35 Compound 3: Compound 13 (5: 5) BD2 3.48 7.11 (0.133, 0.121) 40.8 Example 36 Compound 8: Compound 14 (5: 5) BD2 3.55 7.12 (0.134, 0.122) 42.5 Comparative Example 4 BH1: BH2 (5: 5) BD1 3.98 5.32 (0.135, 0.138) 50.2 Comparative Example 5 BH1: BH2 (7: 3) BD1 3.82 5.54 (0.134, 0.138) 52.8 Comparative Example 6 BH1: BH2 (3: 7) BD1 4.01 5.48 (0.136, 0.139) 51.5 Comparative Example 7 BH1: BH2 (5: 5) BD2 4.02 6.70 (0.133, 0.121) 38.2 Comparative Example 8 BH1: BH2 (7: 3) BD2 3.99 6.56 (0.136, 0.123) 35.1

The organic light emitting device including the compound of the formula according to the present invention uses a compound of the present invention prepared in Preparation Example 6 as a mixed host of the blue organic light emitting device, thereby balancing the hole and electron balance of the organic light emitting device according to the chemical structure Through the device according to the invention exhibits excellent characteristics in terms of efficiency, drive voltage, stability.

101: substrate
102: anode
103: hole injection layer
104: hole transport layer
105: hole control layer
106: light emitting layer
107: electronic control layer
108: electron transport layer
109: hole injection layer
110: cathode

Claims (14)

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

In Chemical Formula 1,
R11 to R14 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
A1, A2, B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,
L1 to L3 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,
R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,
n1 and n2 are each 0 or 1, n1 + n2 is 1,
m1 is an integer of 0 to 8, m2 is an integer of 0 to 7, m3 is an integer of 0 to 9, and when m1 to m3 are each an integer of 2 or more, the substituents in the two or more 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) or (3):
[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,
L1 to L3, R1 to R3, R11 to R14, m1 to m3, A1, A2, B1 and B2 are the same as defined in Chemical Formula 1. The method according to claim 1,
A1, A2, B1 and B2 are the same as or different from each other, and each independently substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 60 carbon atoms. The method according to claim 1,
L1 to L3 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 heteroarylene group containing O, S or N as a substituted or unsubstituted hetero atom having 2 to 60 carbon atoms. The method according to claim 1,
Formula 1 is a compound represented by the following formula (4):
[Formula 4]

In Chemical Formula 4,
R1, R2, R11 to R14, m1, m2, A1, A2, B1, B2, n1, n2, L1 and L2 are the same as defined in Formula 1,
L4 and L5 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,
R4 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,
Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
m4 is an integer of 0 to 8, and when m4 is 2 or more, the substituents in the two or more parentheses are the same as or different from each other,
m5 is an integer of 0 to 3, and when m5 is 2 or more, two or more L5s are the same or different from each other. The method according to claim 1,
Compound represented by Formula 1 is a compound represented by any one of the following compounds:

. The method according to claim 1,
Compound represented by Formula 1 has a band gap energy of 3.0 eV or more. 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 7. . The method according to claim 8,
The organic material layer includes a hole injection layer or a hole transport layer, the hole injection layer or hole transport layer comprises an organic light emitting device comprising the compound. The method according to claim 8,
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 compound. The method according to claim 8,
The organic material layer includes an emission layer, and the emission layer includes the compound. The method according to claim 8,
The organic material layer includes an emission layer, and the emission layer includes the compound as a host of the emission layer. The method according to claim 12,
The light emitting layer is an organic light emitting device comprising one compound as a host of the light emitting layer. The method according to claim 12,
The light emitting layer is an organic light emitting device comprising two or more compounds as a host of the light emitting layer.

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