KR102297723B1 - Polycyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

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

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 the exchange of holes and/or electrons between the electrode and the organic semiconductor material. The organic light emitting device can be roughly divided into two types as follows according to the principle of operation. First, excitons are formed in the organic material layer by photons flowing into the device from an external light source, the excitons are separated into electrons and holes, and the electrons and holes are transferred to different electrodes and used as a current source (voltage source). It is a type of light emitting device. The second is a light emitting device of a type that applies a voltage or current to two or more electrodes to inject holes and/or electrons into an organic semiconductor material layer forming an interface with the electrodes, and operates by the injected electrons and holes.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layered structure composed of different materials in order 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 get In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up. Such an organic light emitting device is known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.

A material used as an organic material layer in an organic light emitting device may be classified into a light emitting material and a charge transporting material, such as a hole injecting material, a hole transporting material, an electron suppressing material, an electron transporting material, an electron injecting material, and the like, according to functions. The light-emitting material includes blue, green, and red light-emitting materials depending on the light-emitting color, and yellow and orange light-emitting materials required to realize better natural colors.

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

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

International Patent Publication No. 2017-126443

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

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

[Formula 1]

In Formula 1,

R11 to R14 are the same as or different from each other, and each independently hydrogen; a 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 heterocyclic ring,

L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

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; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,

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

When m1 is an integer from 0 to 8, m2 is an integer from 0 to 7, m3 is an integer from 0 to 9, and 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 at least one organic material layer provided between the first electrode and the second electrode, wherein at least one organic material layer of the organic material layer includes the compound described above.

The compound described herein may be used as a material for an organic material layer of an organic light emitting device.

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

1 shows 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, an electron transport layer 108. , an example of an organic light emitting device including an electron injection layer 109 and a cathode 110 is shown.

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

The present specification provides a compound represented by the following formula (1). Since the compound represented by the following formula (1) includes one spiro structure in anthracene, when applied to an organic light emitting device, it is possible to drive at a low voltage and thus has excellent power efficiency and excellent light emitting characteristics such as luminance 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 an organic light emitting device.

[Formula 1]

In Formula 1,

R11 to R14 are the same as or different from each other, and each independently hydrogen; a 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 heterocyclic ring,

L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

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; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,

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

When m1 is an integer from 0 to 8, m2 is an integer from 0 to 7, m3 is an integer from 0 to 9, and 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 Formula 1 may be used as a blue host in the emission layer. Currently, a phosphorescent material is commonly used as a compound used in an organic light emitting device, and in particular, a phosphorescent device using an iridium (Ir) complex has been actively studied. Efforts have been made to introduce phosphorescent materials not only in red and green but also in blue light emitting regions, but due to the high singlet energy of the blue host, chemical structural stability and consequent bond dissociation energy (BDE) are related. and the exciton generating region in the light emitting layer. Blue hosts are generally synthesized on the basis of high bandgap energies above 3.0 eV, and are stagnant in the application of anthracene derivatives. An object of the present invention is to provide an organic light emitting device having excellent device characteristics by presenting a compound in which anthracene and a novel spiro structure are combined.

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

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

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

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

As used herein, the term "substituted or unsubstituted" refers to deuterium (-D); halogen group; cyano group (-CN); nitro group; hydroxyl group; silyl group; boron group; an alkyl group; alkoxy group; alkenyl group; alkynyl group; aryloxy group; alkyl thiooxy group; arylthioxy group; cycloalkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a terphenyl group. That is, the terphenyl group may be an aryl group or may be interpreted as a substituent in which three phenyl groups are connected.

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

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

In the present specification, the silyl group may be represented by the formula of _{-SiY a} Y _b Y _{c , wherein Y a} , Y _b and Y _c are each hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. does not

In the present specification, the boron group may be represented by the formula of _{-BY d} Y _{e , wherein Y d} and Y _e are each hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a tert-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 30. 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 a 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, etc., but are not limited thereto.

In the present specification, the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the carbon number of the alkoxy group is 1 to 30. According to another exemplary embodiment, the carbon number of the alkoxy group is 1 to 20. According to another exemplary embodiment, the carbon number of the alkoxy group is 1 to 10. Specific examples of the alkoxy group include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 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 an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but 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 carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, or a quaterphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto no.

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-dimethyl fluorenyl group), and

a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, S and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include pyridyl group, pyrrole group, pyrimidyl group, quinolinyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothio A phenyl group, a carbazolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, an indenocarbazolyl group, etc., but are not limited thereto.

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

In the present specification, in a substituted or unsubstituted ring formed by bonding to each other, "ring" is a hydrocarbon ring; or a heterocyclic ring.

The hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or the 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.

The description of the heterocyclic group may be applied except that the heterocycle is divalent.

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

In the present specification, the description of the above-described heteroaryl group 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 0 or 1, respectively, and n1+n2 is 1.

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

[Formula 2]

[Formula 3]

In Formulas 2 and 3,

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

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 a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; or a substituted or unsubstituted aromatic heterocycle having 2 to 60 carbon atoms.

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

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 1 to 20 carbon atoms an aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group; Or C2 to C30 aromatic hetero unsubstituted or substituted with a C6 to C30 aryl group unsubstituted or substituted with a C1 to C20 trialkylsilyl group, a C1 to C20 alkyl group, or a C1 to C20 alkyl group it is a ring

In another exemplary embodiment, A1, A2, B1 and B2 are the same as or different from each other, and each independently substituted or unsubstituted with a methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, or tert-butyl group an aromatic hydrocarbon ring having 6 to 30 carbon atoms that is unsubstituted or substituted with a cyclic 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 each independently a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or 1 to 20 carbon atoms benzene unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms substituted or unsubstituted 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 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; 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 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 with a phenyl group 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, R11 to R14 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

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, 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, 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 C 2 to C 30 heteroarylene group.

In an exemplary 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 C2 to C60 heteroelement.

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

According to an exemplary embodiment of the present specification, 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; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; a substituted or unsubstituted C1-C30 alkoxy group; a substituted or unsubstituted C6-C30 aryloxy group; A substituted or unsubstituted C 1 to C 30 alkyl thiooxy group; a substituted or unsubstituted C6-C30 arylthioxy group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C 6 to C 60 aryl group; Or a substituted or unsubstituted C2 to C60 heterocyclic group, or a substituted or unsubstituted C2 to C60 ring by combining with an adjacent group.

In an exemplary 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 C 1 to C 20 alkyl group; a substituted or unsubstituted C1-C20 trialkylsilyl group; or a substituted or unsubstituted C6-C30 aryl group.

In another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted methyl group; a substituted or unsubstituted isopropyl group; a substituted or unsubstituted tert-butyl group; a 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, and when m1 is 2, two R1s 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, and when m2 is 2, two R2s are the same as or different from each other.

According to an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; a substituted or unsubstituted C 6 to C 60 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, R3 is hydrogen; heavy hydrogen; a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C20 trialkylsilyl group, a C1-C20 alkyl group, or a C6-C30 aryl group; or a heterocyclic group having 2 to 60 carbon atoms which is 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; a 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; a 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; a 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; a phenanthrenyl 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 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; a carbazolyl 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 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, and when m2 is 2 or more, two or more '-L3-R3' are the same as or different from each other.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formula 4 below.

[Formula 4]

In Formula 4,

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

L4 and L5 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R4 is hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,

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

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

m5 is an integer of 0 to 3, and when m5 is 2 or more, L5 of 2 or more are the same as 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 another exemplary embodiment, the L4 is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted C 2 to C 30 heteroarylene group.

In 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 heteroarylene group containing O, S, or N as a substituted or unsubstituted C2 to C60 heteroelement.

According to another exemplary embodiment, the L4 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted fluorenylene group; A 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; a fluorenylene group substituted with a methyl group; dibenzofuranylene group; or a dibenzothiophenylene group.

According to an exemplary embodiment of the present specification, R4 is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

According to another exemplary embodiment, R4 is hydrogen; heavy hydrogen; a 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 an exemplary embodiment of the present specification, m4 is an integer of 0 to 2, and when m4 is 2, two '-L4-R4' are the same as or different from each other.

In the exemplary embodiment of the present specification, m5 is an integer of 0 to 2, and when m5 is 2, two L5s are the same as or different from each other.

According to an exemplary embodiment of the present specification, 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 another exemplary embodiment, the L5 is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted C 2 to C 30 heteroarylene group.

In an exemplary 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 C2 to C60 heteroelement.

According to another exemplary embodiment, the L5 is a direct bond; a 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; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted benzofluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted carbazole group; a 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, a tert-butyl group, or a trimethylsilyl group; terphenyl group; naphthyl group; a fluorenyl group unsubstituted or substituted with a methyl group; a benzofluorenyl group substituted with a methyl group; phenanthrenyl group; dibenzofuranyl group; dibenzothiophenyl group; a carbazole group substituted with a phenyl group; naphthobenzofuranyl group; or a naphthobenzothiophenyl group.

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

In an exemplary 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, and 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 energy transfer to the dopant is smoothly performed, a device having excellent luminous efficiency can be obtained.

The bandgap energy (E _bg ) may be obtained by measuring the LUMO energy and the HOMO energy of the molecule.

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

Optimize the input structure using density functional theory to determine the molecular structure of the chemical. For DFT calculation, BPW91 calculation method (Becke exchange and Perdew correlation-correlation functional) and DNP (double numerical basis set including polarization functional) basis set are used. The BPW91 calculation method is 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 basis set was published in the paper 'B. Delley, J. Chem. Phys., 92, 508 (1990).

Biovia's 'DMol3' package can be used to perform calculations with the full-density function method. If the optimal molecular structure is determined using the method given above, the energy level that electrons can occupy can be obtained as a result. The HOMO energy refers to the orbital energy of the highest energy level among molecular orbitals filled with electrons when the energy of the neutral state is obtained, and the LUMO energy corresponds to the orbital energy of the lowest energy level among molecular orbitals not filled with electrons.

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

For the optimal molecular structure determined using the universal density function method, the energy when the electron arrangement is singlet and triplet is calculated using the time-dependent universal 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 Reaction 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 Formula 1 above, and X means a halogen group or a sulfonyl group.

In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of Formula 1 above. In addition, in the present specification, the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents into the core structure of the structure as described above.

In addition, by introducing various substituents into the core structure of the structure as described above, a compound having the intrinsic properties of the introduced substituents can be synthesized. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, an electron suppression material, a light emitting layer material, and an electron transport layer material used in manufacturing an organic light emitting device into the core structure, the conditions required for each organic material layer are satisfied. substances can be synthesized.

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 the compound represented by the above-described Chemical Formula 1.

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 for forming one or more organic material layers using the above-described compound.

The compound represented by Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, 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 have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention is an organic material layer, a hole injection layer, a hole control layer, a hole transport layer, a layer that transports and injects holes 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, electron It may have a structure including a layer that simultaneously transports and injects electrons. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material 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 above-described 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 above-described 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 above-described compound.

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

In another exemplary embodiment, the organic material layer may include an emission layer, and the emission layer may include the above-described compound as a host of the emission layer and further include a dopant. In this case, the dopant of the emission layer may be included in an amount of 0.1 parts by weight or more and 10 parts by weight or less, preferably 0.5 parts by weight or more and 5 parts by weight or less, based on 100 parts by weight of the host.

In another exemplary embodiment, the organic material layer may include a light emitting layer, and the light emitting layer may include one kind of compound as a host of the light emitting layer, and the one kind of compound may be the aforementioned compound.

According to another exemplary embodiment, the organic material layer includes an emission layer, the emission layer includes two or more compounds as a host of the emission layer, and the two or more types of compounds may be the aforementioned compounds.

According to an exemplary embodiment of the present invention, the organic material layer includes a light emitting layer, the light emitting layer may include one (single type) or two or more compounds as a host of the light emitting layer, wherein the two or more types of compounds are the above-mentioned compounds And it may include a compound represented by the following formula (X). In this case, the weight ratio of the compound represented by Formula 1 to the compound represented by Formula X (the weight of Formula 1 : the weight of Formula X) may be 1:10 to 10:1.

[Formula X]

In the formula (X),

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

In an exemplary 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 C 1 to C 20 alkyl group; a substituted or unsubstituted C6-C30 aryl group; 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 may include a light emitting layer, the light emitting layer may include the above-described 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 includes an emission layer, the emission layer includes the above-described compound as a dopant of the emission layer, a fluorescent host or a phosphorescent host, and may be used together with an iridium-based (Ir) dopant.

In the organic light emitting device of the present invention, the organic material layer may include an electron blocking layer, and the electron blocking layer may include the above-described compound.

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

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

The organic light emitting device may have, for example, a stacked structure as follows, 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 blocking layer / electron transport layer / cathode

(15) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(16) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking 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 that simultaneously injects and transports electrons / cathode

(19) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking 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, 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 exemplified. In such a structure, the compound may be included in the light emitting layer 106 .

For example, the organic light emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal or a conductive metal oxide or an alloy thereof on a substrate. is deposited to form an anode, 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 is formed thereon, and then a material that can be used as a cathode is deposited 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 that simultaneously injects and transports electrons, an electron control layer, an electron suppression layer, a light emitting layer and an electron transport layer, an electron injection layer, a layer that simultaneously injects and transports electrons. It may be a multi-layer structure including, but is not limited to, and may have a single-layer structure. In addition, the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

The anode is an electrode for injecting holes, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode 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); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode 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; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer. As the hole injection material, holes can be well injected from the anode at a low voltage. 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 organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, and conductive polymers of polyaniline and polythiophene series, but are not limited thereto. The thickness of the hole injection layer may be 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement There are advantages to avoiding this.

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

An additional hole buffer layer may be 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 blocking layer may be provided between the hole transport layer and the light emitting layer. For the electron-blocking layer, the above-described compound or a material known in the art may be used.

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

The electron control layer may include a triazine-based compound, but is not limited thereto.

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

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

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

The electron transport layer may serve to facilitate the transport of electrons. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Specific examples include Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage that the electron transport characteristics can be prevented from being lowered, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from being increased to improve the movement of electrons. There are advantages that can be

The electron injection layer may serve to facilitate injection of electrons. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and , a compound having excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

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

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

Hereinafter, examples will be given to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present application is not to be construed as being limited to the embodiments described below. The embodiments of the present application are provided to more completely explain the present specification to those of ordinary skill in the art.

< manufacturing example >

manufacturing 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, 2.5M n-BuLi (1.5eq) was added dropwise and 30 minutes later, SM2 (1.05eq) listed in Table 1 below. was added and raised to room temperature (RT), followed by stirring for 1 hour. 1N HCl (excess) was added, stirred for 30 minutes, the layers were separated, the solvent was removed, and the obtained solid was purified with ethyl acetate. Then, 1 ml of sulfuric acid was added dropwise and refluxed with stirring. After lowering the temperature to room temperature and neutralizing with water, the filtered solid was recrystallized with tetrahydrofuran and ethyl acetate to prepare A1-1 to A1-12 in Table 1 below. In the above preparation, R ₁₀₁ to R ₁₀₄ each means a substituent, and a, b, c and d each mean 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

manufacturing example 2 (Step 1-2 or Step 2-2)

Step 1-2 and Step 2- 2 of synthesis

A1-1 to A1-12 (leq) synthesized in Preparation Example 1 and alkyliodide to phenyliodide (3.5eq, SM2) described in Table 2 were added under nitrogen, followed by stirring at room temperature for 12 hours. . After completion of the reaction, methanol (excess) was added and filtered. The solid was extracted with chloroform and distilled water, concentrated, and column separated (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 mean a substituent, and a, b, c and d each mean 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

manufacturing example 3 (Step 1-3 or Step 2-3)

Step 1-3 and Step 2- 3 of synthesis

After dissolving one of the B1-5, B1-12, and B1-13 (leq) in tetrahydrofuran (THF, excess), the temperature was lowered to -78°C, and then 2.5M n-BuLi (1.5eq) was added dropwise and 30 After minutes, SM2 (1.3eq) shown in Table 3 was added, and the mixture was raised to room temperature and stirred for 1 hour. 1N HCl (excess) was added, stirred for 30 minutes, the layers were separated, the solvent was removed, and the obtained solid was purified with ethyl acetate. After lowering the temperature to room temperature and neutralizing with water, the filtered solid was recrystallized with tetrahydrofuran and ethyl acetate to prepare C1-1 to C1-3 in Table 3 below. In the above preparation, R ₁₀₁ to R ₁₀₄ , R' and R" each mean a substituent, and a, b, c and d each mean 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

manufacturing example 4 (Step 1-4 or Step 2-4)

Step 1-4 and Step 2- 4 of synthesis

After adding one of C1-1 to C1-3 (leq) and SM2 (1.05eq) shown in Table 4 below to tetrahydrofuran (excess), a 2M aqueous potassium carbonate solution (30 volume ratio compared to THF) was added, and tetra Kistriphenyl-phosphinopalladium (2 mol%) was added, followed by heating and stirring for 10 hours. After the reaction was terminated by lowering the temperature to room temperature, the potassium carbonate aqueous solution was removed and the layers were separated. After removal of the solvent, C2-1 to C2-4 of Table 4 were prepared by vacuum distillation. In the above preparation, R ₁₀₁ to R ₁₀₄ , R' and R" each mean a substituent, L ₁ and L ₂ are each a linking group, and a, b, c and d each mean 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

manufacturing example 5 (Step 1-5 or Step 2-5)

Step 1-5 and Step 2- 5 of synthesis

One (leq) of C2-1 to C2-4 was dissolved in chloroform (excess), and then perfluorofutansulfonyl fluoride (2.5eq, SM2) was slowly added dropwise at room temperature and stirred at room temperature for 3 hours. did. After extraction with water and chloroform at room temperature, the mixture was concentrated to obtain C3-1 to C3-4 in Table 5 as a white solid with hexane. In the above preparation, R ₁₀₁ to R ₁₀₄ , R' and R" each mean a substituent, L ₁ and L ₂ are each a linking group, and a, b, c and d each mean 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

manufacturing example 6 (compound 1 to compound 20 of synthesis)

Step 1-6 and Step 2- 6 of synthesis

One of B1-1 to B1-14, C3-1 to C3-4, B1-2, A1-1 and B1-4 (leq) and SM2 (1.03eq) listed in Table 6 below were mixed with tetrahydrofuran (excess) After addition to 2M potassium carbonate aqueous solution (30 volume ratio relative to THF) was added, tetrakistriphenyl-phosphinopalladium (2 mol%) was added, and then heated and stirred for 10 hours. After the reaction was terminated by lowering the temperature to room temperature, the potassium carbonate aqueous solution was removed and the layers were separated. After removal of the solvent, compounds 1 to 20 of Table 6 were prepared by recrystallization with tetrahydrofuran and ethyl acetate. In the above preparation, R ₁₀₁ to R ₁₀₄ , R' and R" each mean a substituent, L ₁ and L ₂ are each a linking group, and a, b, c and d each mean 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 compound 6 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 / comparative example >

< Example 1> OLED manufacture of

As an anode, a substrate on which 70/1000/70Å of ITO/Ag/ITO was deposited was cut into a size of 50 mm x 50 mm x 0.5 mm, put in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of Fischer Co., and the distilled water was manufactured by Millipore Co. Secondary filtered distilled water was used as a filter of the product. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the prepared anode, HI-1 was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer, and HT1, a material for transporting holes, was vacuum-deposited thereon to a thickness of 1150 Å to form a hole transport layer. Then, a hole control layer was formed using HT2 (150 Å), and then the host compound 1 synthesized in Preparation Example 6 and the dopant BD1 (2 wt %) were vacuum-deposited to a thickness of 360 Å to form a light emitting layer. Thereafter, ET1 was deposited by 50 Å to form an electron control layer, and the compound ET2 and Liq were mixed at a ratio of 7:3 to form an electron transport layer having a thickness of 250 Å. Magnesium and lithium fluoride (LiF) with a thickness of 50 Å were sequentially formed as an electron injection layer <EIL>, and then 200 Å of magnesium and silver (1:4) were formed as an anode. Then, CP1 was deposited with 600 Å 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 prepared in the same manner as in Example 1, except that compounds 1 to 20 synthesized in Preparation Example 6 were used as the host material of the emission layer, respectively, and BD1 or BD2 was used as the dopant material of the emission layer. The experimental results of the organic light emitting devices of 21 and Comparative Examples 1 to 3 are shown in Table 7 below. In Table 7 below, the lifetime is a measurement of the time at which the initial luminance becomes 95% at a current density ^{of 20 mA/cm 2 .}

Experimental example
20 mA/cm2 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 of

As an anode, a substrate on which 70/1000/70Å of ITO/Ag/ITO was deposited was cut into a size of 50 mm x 50 mm x 0.5 mm, put in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of Fischer Co., and the distilled water was manufactured by Millipore Co. Secondary filtered distilled water was used as a filter of the product. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the prepared anode, HI-1 was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer, and HT1, a material for transporting holes, was vacuum-deposited thereon to a thickness of 1150 Å to form a hole transport layer. Then, a hole control layer was formed using HT2 (150 Å), and then the compound 1 synthesized in Preparation Example 6 and the BH1 were mixed in a weight ratio of 50:50, and at the same time a dopant BD1 (2% by weight) was co-deposited. to form a light emitting layer to a thickness of 360 Å. Thereafter, ET1 was deposited by 50 Å to form an electron control layer, and the compound ET2 and Liq were mixed at a ratio of 7:3 to form an electron transport layer having a thickness of 250 Å. Magnesium and lithium fluoride (LiF) with a thickness of 50 Å were sequentially formed as an electron injection layer <EIL>, and then 200 Å of magnesium and silver (1:4) were formed as an anode. Then, CP1 was deposited with 600 Å 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 of

Example 22 prepared in the same manner as in Example 22, except that compounds 1 to 20 synthesized in Preparation Example 6 were used as the mixed host material of the light emitting layer and BD1 or BD2 was used as the dopant material of the light emitting layer. The experimental results of the organic light emitting devices of to 36 and Comparative Examples 4 to 8 are shown in Table 8 below. In Table 8 below, the lifetime is a measurement of the time at which the initial luminance becomes 95% at a current density ^{of 20 mA/cm 2 .}

Experimental example
20 mA/cm2 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 containing the compound of the present invention uses the compound of the present invention prepared in Preparation Example 6 as a mixed host of the blue organic light emitting device, thereby balancing the holes and electrons of the organic light emitting device according to the chemical structure. Through this, the device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage, and stability.

101: substrate
102: positive electrode
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)

A compound represented by the following formula (4):
[Formula 4]

In Formula 4,
L1 or L2 binds to position 10 of the anthracene,
R11 to R14 are the same as or different from each other, and each independently hydrogen; an alkyl group having 1 to 10 carbon atoms; Or an aryl group having 6 to 30 carbon atoms,
A1, A2, B1 and B2 are the same as or different from each other, and each independently an aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group, an aryl group, an alkylaryl group, or an alkylsilyl group; Or an aromatic heterocyclic ring containing O or S having 3 to 30 carbon atoms,
L1 and L2 are the same as or different from each other, and each independently a direct bond; an arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with an alkyl group; Or a heteroarylene group having 3 to 30 carbon atoms,
R1 and R2 are the same as or different from each other, and each independently hydrogen; a silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; an alkyl group having 1 to 10 carbon atoms; Or an aryl group having 6 to 30 carbon atoms,
L4 and L5 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,
R4 is hydrogen; an alkyl group having 1 to 10 carbon atoms; Or an aryl group having 6 to 30 carbon atoms,
Ar1 is a phenyl group unsubstituted or substituted with deuterium, an alkylsilyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 carbon atoms; an aryl group having 10 to 30 carbon atoms that is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; Or a C 3 to C 30 heterocyclic group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms,
n1 and n2 are each 0 or 1, n1+n2 is 1,
m1 is an integer from 0 to 8, m2 is an integer from 0 to 7, and when m1 and m2 are each an integer of 2 or more, the substituents in the parentheses of 2 or more are the same as or different from each other,
m4 is an integer from 0 to 8, and when m4 is 2 or more, the substituents in the parentheses of 2 or more are the same as or different from each other,
m5 is an integer of 0 to 3, and when m5 is 2 or more, L5 of 2 or more are the same as or different from each other. delete delete delete delete The method according to claim 1,
The compound represented by Formula 4 is a compound represented by any one of the following compounds:

.

The method according to claim 1,
The compound represented by Formula 4 is a compound having 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 an organic compound according to any one of claims 1, 6 and 7 light emitting element. 9. The method of claim 8,
The organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound. 9. The method of claim 8,
The organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound. 9. The method of claim 8,
The organic material layer includes an emission layer, and the emission layer includes the compound. 9. The method of claim 8,
The organic material layer includes an emission layer, and the emission layer includes the compound as a host of the emission layer. 13. The method of claim 12,
The light emitting layer is an organic light emitting device including one kind of compound as a host of the light emitting layer. 13. The method of 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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