WO2020130623A1

WO2020130623A1 - Polycyclic compound and organic light-emitting device comprising same

Info

Publication number: WO2020130623A1
Application number: PCT/KR2019/017993
Authority: WO
Inventors: 금수정; 홍완표; 이동훈; 서상덕; 김경희
Original assignee: 주식회사 엘지화학
Priority date: 2018-12-18
Filing date: 2019-12-18
Publication date: 2020-06-25
Also published as: KR20200075777A; CN112912365B; KR102280868B1; CN112912365A

Abstract

The present specification provides a compound of chemical formula 1 and an organic light-emitting device comprising same.

Description

Polycyclic compound and organic light emitting device including same

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0164430, filed with the Korean Patent Office on December 18, 2018, the entire contents of which are incorporated herein.

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

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layer structure composed of different materials, 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 a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode and electrons are injected at the cathode, and excitons are formed when the injected holes meet the electrons. When it falls to the ground again, it will shine. It is known that such an organic light emitting device has characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.

Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppressing materials, electron transport materials, and electron injection materials, depending on their function. The light emitting materials include blue, green, and red light emitting materials, and yellow and orange light emitting materials necessary for realizing a better natural color depending on the light emitting color.

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

In order to sufficiently exhibit the excellent characteristics of the above-described organic light emitting device, materials constituting an 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, are stable and efficient materials It is supported by, and the development of new materials continues to be required.

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

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

[Formula 1]

In Chemical Formula 1,

L1, L2 and L11 to L14 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R2 to R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n1 is an integer from 0 to 4, and when n1 is 2 or more, 2 or more R1s are the same or different from each other.

In addition, the present invention is a first electrode; A second electrode; And one or more organic material layers provided between the first electrode and the second electrode, and at least one layer of the organic material layer includes the above-described compound.

The compound according to the exemplary embodiment of the present specification may be used as a material of an organic material layer of an organic light emitting device.

The compound according to the exemplary embodiment of the present specification has a structure in which a naphthalene and a 6-membered aliphatic ring (cyclohexane or cyclohexene) are condensed as a core structure in the compound, and when applied to an organic light emitting device, has excellent luminous efficiency, An organic light emitting device having a low driving voltage and high efficiency can be obtained.

1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.

2 is composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron injection and electron transport layer (8) and a cathode (4) at the same time An example of an organic light emitting device is shown.

[Description of codes]

1: Substrate

2: anode

3: light emitting layer

4: Cathode

5: hole injection layer

6: hole transport layer

7: emitting layer

8: electron transport layer

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

The present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

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

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

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

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

The term "substituted or unsubstituted" in this specification is deuterium (-D); Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Silyl group; Boron group; Alkyl groups; Alkoxy groups; Cycloalkyl group; Aryl group; Amine group; And 1 or 2 or more substituents selected from the group consisting of heterocyclic groups, or substituted with two or more substituents among the above-described substituents, or having no substituents. For example, "a substituent having two or more substituents" 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 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 is specifically trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, dimethylphenylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. There is, but is not limited to this.

In the present specification, the boron group may be represented by the formula -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. The boron group may include, but is not limited to, trimethyl boron group, triethyl boron group, tert-butyl dimethyl boron group, triphenyl boron group, phenyl boron group, and the like.

In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group are methyl group, ethyl group, 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 is not limited to these.

In this 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 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 an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, a cyclopropyl group, 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 is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl 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 combine with each other to form a spiro structure.

When the fluorenyl group is substituted,

Spirofluorenyl groups such as,

(9,9-dimethylfluorenyl group), and

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

In the present specification, the heterocyclic group is a hetero atom and is a ring group containing one or more of N, O, S, and Se, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group , Carbazole group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, indolocarbazole group, and the like, but are not limited to these.

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

In this specification, "adjacent" A group may mean a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent located closest to the corresponding substituent and the other substituent substituted on the atom in which the substituent is substituted. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other. In the present specification, R2 and R3 of Formula 1 described above may be adjacent groups, R4 and R5 may be adjacent groups, and R6 and R7 may be adjacent groups.

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

According to an exemplary embodiment of the present specification, the formula 1 is represented by the following

formula

2 or 3.

[Formula 2]

[Formula 3]

In

Chemical Formulas

2 and 3,

The definitions of L1, L2, L11 to L14, Ar1 to Ar4, R1 to R7 and n1 are as defined in Chemical Formula 1.

In one embodiment of the present specification, L1, L2, and L11 to L14 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In another exemplary embodiment, the L1, L2 and L11 to L14 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to another exemplary embodiment, L1, L2 and L11 to L14 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; Or a substituted or unsubstituted terphenyl group.

In another exemplary embodiment, the L1, L2 and L11 to L14 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Naphthylene group; Or a terphenyl group.

According to the exemplary embodiment of the present specification, L1 and L2 are a direct bond.

In one embodiment of the present specification, L11 to L14 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In another exemplary embodiment, L11 to L14 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; Or a substituted or unsubstituted terphenyl group.

In another exemplary embodiment, L11 to L14 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Naphthylene group; Or a terphenylene group.

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

[Formula 4]

In Chemical Formula 4,

The definitions of L11 to L14, Ar1 to Ar4, R1 to R7 and n1 are as defined in Chemical Formula 1.

In one embodiment of the present specification, R2 to R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Hydroxy group; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, R2 to R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Hydroxy group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; 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, R2 to R7 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; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, R2 to R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms; Or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, R2 to R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.

In another exemplary embodiment, R2 to R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; It is a phenyl group unsubstituted or substituted with a methyl group.

In one embodiment of the present specification, at least one of R2 to R7 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, at least two of the R2 to R7 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, two of the R2 to R7 are alkyl groups having 1 to 20 carbon atoms; Or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

In another exemplary embodiment, two of the R2 to R7 are methyl groups; Or a phenyl group unsubstituted or substituted with a methyl group.

In another exemplary embodiment, two of the R2 to R7 are alkyl groups having 1 to 20 carbon atoms; Or an aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, two of the R2 to R7 are methyl groups; Or a phenyl group.

According to an exemplary embodiment of the present specification, the formula 1 is represented by the formula (5).

[Formula 5]

In Chemical Formula 5,

The definitions of L1, L2, L11 to L14, Ar1 to Ar4, R1, R6, R7 and n1 are as defined in Formula 1 above.

formula

6 or 7.

[Formula 6]

[Formula 7]

In

Chemical Formulas

6 and 7,

The definitions of L1, L2, L11 to L14, Ar1 to Ar4, R1 and n1 are as defined in Formula 1 above,

R11 and R12 are the same as or different from each other, and each independently an substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

R13 and R14 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 cycloalkyl group having 3 to 30 carbon atoms; 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,

n13 and n14 are each an integer of 0 to 5, and when n13 and n14 are each 2 or more, the substituents in 2 or more parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, R11 and R12 are the same as or different from each other, and each independently an substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

According to another exemplary embodiment, R11 and R12 are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; Or a substituted or unsubstituted butyl group.

In another exemplary embodiment, R11 and R12 are the same as or different from each other, and each independently a methyl group; Ethyl group; Propyl group; Or a butyl group.

According to another exemplary embodiment, R11 and R12 are methyl groups.

According to an exemplary embodiment of the present specification, the n13 and n14 are each an integer of 0 to 2, and when the n13 and n14 are each 2, the substituents in the two parentheses are the same or different.

According to another exemplary embodiment, n13 is an integer from 0 to 2, and when n13 is 2, two R13s are the same as or different from each other.

According to another exemplary embodiment, n14 is an integer from 0 to 2, and when n14 is 2, two R14s are the same or different.

In one embodiment of the present specification, R13 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

According to another exemplary embodiment, R13 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; Or a substituted or unsubstituted butyl group.

In another exemplary embodiment, R13 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; Propyl group; Or a butyl group.

In another exemplary embodiment, R13 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a methyl group.

In another exemplary embodiment, R13 and R14 are the same as or different from each other, and each independently hydrogen; Or deuterium.

According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Hydroxy group; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Hydroxy group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; 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, R1 is hydrogen or deuterium.

According to an exemplary embodiment of the present specification, the n1 is 0 or 1.

According to the exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a heterocyclic group containing O, S or N as a substituted or unsubstituted hetero atom having 2 to 60 carbon atoms.

In another exemplary embodiment, Ar1 to Ar4 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 aryl group having 6 to 30 carbon atoms; Or a heterocyclic group containing O, S or N as a substituted or unsubstituted hetero atom having 2 to 30 carbon atoms.

According to another exemplary embodiment, Ar1 to Ar4 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; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, substituted or unsubstituted silyl groups, and substituted or unsubstituted alkyl groups; Or a heterocyclic group containing O, S or N as a hetero atom having 2 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, substituted or unsubstituted silyl groups and substituted or unsubstituted alkyl groups. .

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently substituted with one or more substituents selected from the group consisting of deuterium, substituted or unsubstituted silyl groups, and substituted or unsubstituted alkyl groups, or An unsubstituted aryl group having 6 to 30 carbon atoms; Or a heterocyclic group containing O, S or N as a hetero atom having 2 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, substituted or unsubstituted silyl groups and substituted or unsubstituted alkyl groups. .

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently comprises deuterium, a silyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, and an alkyl group substituted or unsubstituted with deuterium. An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group; Or a deuterium, a C1-C10 hetero atom substituted or unsubstituted with one or more substituents selected from the group consisting of a silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms and an unsubstituted or substituted alkyl group, O, S Or a heterocyclic group containing N.

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently comprises deuterium, a silyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, and an alkyl group substituted or unsubstituted with deuterium. An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group; Or a heterocyclic group containing O, S or N as a hetero atom having 2 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group unsubstituted or substituted with deuterium.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted indolocarbazole group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted naphthobenzothiophene group. When the substituents are substituted, it may be substituted with one or more substituents selected from the group consisting of deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, and an alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted indolocarbazole group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted naphthobenzothiophene group. When the substituents are substituted, it may be substituted with one or more substituents selected from the group consisting of deuterium, a trialkylsilyl group having 1 to 20 carbon atoms, and an alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently substituted with deuterium, trimethylsilyl group, tert-butyldimethylsilyl group, methyl group, isopropyl group, tert-butyl group, and deuterium A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of methyl groups; A biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, trimethylsilyl group, tert-butyldimethylsilyl group, methyl group, isopropyl group, tert-butyl group and methyl group substituted with deuterium; A naphthyl group unsubstituted or substituted with a phenyl group; A terphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, trimethylsilyl group, tert-butyldimethylsilyl group, methyl group, isopropyl group, tert-butyl group and methyl group substituted with deuterium; A fluorenyl group unsubstituted or substituted with a methyl group; A benzofluorenyl group unsubstituted or substituted with a methyl group; Carbazole; Indolocarbazole; A dibenzofuran group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, methyl group, isopropyl group, tert-butyl group and methyl group substituted with deuterium; A naphthobenzofuran group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, methyl group, isopropyl group, tert-butyl group and methyl group substituted with deuterium; A dibenzothiophene group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, methyl group, isopropyl group, tert-butyl group and methyl group substituted with deuterium; Or a naphthobenzothiophene group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, methyl group, isopropyl group, tert-butyl group and methyl group substituted with deuterium.

In one embodiment of the present specification, -L1-N(-L11-Ar1)(-L12-Ar2) and -L2-N(-L13-Ar3)(-L14-Ar4) of Chemical Formula 1 are the same as each other .

In one embodiment of the present specification, -N(-L11-Ar1)(-L12-Ar2) and -N(-L13-Ar3)(-L14-Ar4) of Chemical Formula 1 are the same as each other.

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

According to an exemplary embodiment of the present specification, the compound of Formula 1 may be prepared as in Scheme 1 below. Various compounds corresponding to Formula 1 of the present application may be synthesized using the synthesis process as shown in Reaction Scheme 1 below, and the substituents may be combined by a method known in the art, and the type, position and number of the substituents are described in the art. It can be changed according to the technology known in the field.

In Scheme 1, R1 and R2 are the same as the definitions of R2 to R7 in Formula 1, and Ar1 and Ar2 in Scheme 1 are -L11-Ar1, -L12-Ar2, -L13-Ar3 in Formula 1, And -L14-Ar4. In addition, in Reaction Scheme 1, the synthesis process of Formula 1 in which a substituent is attached only at a specific position is illustrated, but the above Chemical Formula 1 range is obtained by a synthetic method known in the art using starting materials, intermediate materials, etc., known in the art. Compounds corresponding to can be synthesized.

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

In addition, by introducing various substituents to the core structure of the above structure, it is possible to synthesize a compound having intrinsic properties of the introduced substituents. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, an electron suppression material, a light emitting layer material, and an electron transport layer material used in manufacturing an organic light emitting device, the conditions required for each organic material layer are satisfied. You can synthesize a substance to let.

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, and at least one layer of the organic material layer comprises a compound represented by 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 one or more organic material layers are formed using the compound represented by Chemical Formula 1 above.

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

The organic material layer of the organic light emitting device of the present 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 a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection as an organic material layer, an electron suppressing layer, a light emitting layer, an electron transport layer and an electron injection layer, a layer that simultaneously conducts electron transport and electron injection It may have a structure including a. However, the structure of the organic light emitting device is not limited thereto, and may include fewer or more 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 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 above-described compound.

In the organic light emitting device of the present specification, 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 includes a light emitting layer, and the light emitting layer includes the above-described compound as a dopant in the light emitting layer.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes the above-described compound as a dopant in the light emitting layer, and further includes a host.

The organic light emitting diode according to the exemplary embodiment of the present specification includes a light emitting layer, and the light emitting layer further includes a compound represented by the following Chemical Formula H in addition to the compound represented by the Chemical Formula 1. Specifically, the above-mentioned compound is included as a dopant of the light emitting layer, and the compound represented by the following formula H is included as a dopant of the light emitting layer.

[Formula H]

In the formula H,

L21 to L23 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,

R21 to R27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a is 0 or 1,

Formula H may include one or more deuterium.

In one embodiment of the present specification, when a is 0, a position of -L23-Ar23 is connected to hydrogen or deuterium.

In one embodiment of the present specification, L21 to L23 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.

In one embodiment of the present specification, L21 to L23 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 containing N, O, or S.

In one embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently a direct bond; A deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms or an arylene group having 6 to 30 carbon atoms unsubstituted or substituted with a heteroaryl group having 2 to 30 carbon atoms; Or a heteroarylene group having 2 to 30 carbon atoms unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L21 to L23 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 divalent dibenzofuran group; Or a substituted or unsubstituted divalent dibenzothiophene group.

In one embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Or a naphthylene group, L21 to L23 may each contain one or more deuterium.

In one embodiment of the present specification, L21 is a direct bond.

In one embodiment of the present specification, L22 is a direct bond; Or a phenylene group.

In one embodiment of the present specification, L23 is a direct bond.

In one embodiment of the present specification, L1 may include deuterium. Specifically, L1 contains 1 or more deuterium.

In one embodiment of the present specification, L2 may include deuterium. Specifically, L2 contains one or more deuterium.

In one embodiment of the present specification, L3 may include deuterium. Specifically, L3 contains one or more deuterium.

In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently 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 one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted naphthobenzothiophene group.

In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthryl group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group, Ar21 to Ar23 may each contain one or more deuterium.

In one embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthryl group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group.

In one embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; 1-naphthyl group; 2-naphthyl group; Or dibenzofuran group.

In one embodiment of the present specification, Ar23 is a phenyl group; Biphenyl group; It is a naphthyl group.

In one embodiment of the present specification, Ar23 is a naphthyl group.

In one embodiment of the present specification, Ar1 may include deuterium. Specifically, Ar1 contains one or more deuterium.

In one embodiment of the present specification, Ar2 may include deuterium. Specifically, Ar2 contains one or more deuterium.

In one embodiment of the present specification, Ar3 may include deuterium. Specifically, Ar3 contains one or more deuterium.

In one embodiment of the present specification, Ar21 and Ar22 are different from each other.

In one embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar21 is an aryl group unsubstituted or substituted with deuterium, and Ar22 is an aryl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar21 is an aryl group unsubstituted or substituted with deuterium, and Ar22 is a heteroaryl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R21 to R27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R21 to R27 are the same as or different from each other, and each independently hydrogen or deuterium.

In one embodiment of the present specification, R21 to R27 are hydrogen.

In one embodiment of the present specification, R21 to R27 are deuterium.

When the formula (H) includes one or more deuterium, characteristics of the long life of the device are improved.

In one embodiment of the present specification, Chemical Formula H is represented by the following Chemical Formula H01 or H02.

[Formula H01]

[Formula H02]

In the above formula H01 and H02,

The definitions of L21 to L23 and Ar21 to Ar23 are as defined in Formula H, D means deuterium, k1 is an integer from 0 to 8, and k2 is an integer from 0 to 7.

In one embodiment of the present specification, the compound represented by Chemical Formula H is any one selected from the following compounds.

When the compound of the present invention is included as a dopant in the light emitting layer, and the formula (H) is included as a host, the content of the dopant is 1 part by weight to 20 parts by weight based on 100 parts by weight of the host, preferably 1 part by weight to 5 parts by weight It can contain. When the above range is satisfied, there is an advantage that the driving voltage of the manufactured organic light emitting device is low and the luminous efficiency is high.

In another exemplary embodiment, the organic material layer includes a light emitting layer, the light emitting layer includes the above-described compound as a dopant in the light emitting layer, a fluorescent host or a phosphorescent host, and other organic compounds, metals or metal compounds as dopants It can contain.

The compound represented by Chemical Formula H may be included as one type in the organic material layer (specifically, the light emitting layer), or may be included as two or more types. Specifically, the first host represented by Chemical Formula H and the second host represented by Chemical Formula H may be included in the organic material layer.

The weight ratio of the first host represented by Chemical Formula H and the second host represented by Chemical Formula H is 95:5 to 5:95, more preferably 30:70 to 70:30.

In another exemplary embodiment, the first host and the second host are different from each other.

In another exemplary embodiment, Ar21 and Ar22 of the first host represented by Chemical Formula H are the same or different from each other, and each independently an substituted or unsubstituted aryl group; Ar21 of the second host represented by Formula H is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted heteroaryl group.

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

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

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

According to an exemplary embodiment of the present invention, the maximum emission peak of the emission layer including the compound represented by Chemical Formula 1 is 400 nm to 500 nm.

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

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

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

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

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

(3) anode/hole transport layer/light emitting layer/electron transport layer/cathode

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

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

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

(7) anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode

(8) anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode

(9) anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode

(10) anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode

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

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

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

(14) anode/hole injection layer/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode

(15) Anode/hole injection layer/hole transport layer/light emitting layer/layer/cathode simultaneously performing electron injection and electron transport

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

1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In such a structure, the compound may be included in the light emitting layer 3.

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

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

The organic material layer may be a multi-layered structure including a hole injection layer, a hole transport layer, a layer simultaneously performing hole injection and hole transport, an electron suppressing layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron injection and electron transport layer, and the like. However, it is not limited thereto, and may be a single-layer structure. In addition, the organic material layer may use a variety of polymer materials to reduce the number of solvent processes (e.g., spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer) rather than deposition. Can be prepared in layers.

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

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

The hole injection layer is a layer that serves to smoothly inject holes from the anode to the light emitting layer. As the hole injection material, a hole injection material can be well injected with holes from the anode at a low voltage, and HOMO (highest occupied) of the hole injection material It is preferable that the molecular orbital is 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 substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto. The thickness of the hole injection layer may be 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing the hole injection characteristics from being deteriorated. If 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 is an advantage that can be prevented.

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

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

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

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

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

A hole suppressing layer may be provided between the electron transport layer and the light emitting layer, and the hole suppressing layer is a layer that blocks the arrival 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 complex, and the like, 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 receiving electrons well from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons 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. When the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing the electron transport properties from deteriorating, and when it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from rising to improve the movement of electrons. There is an advantage.

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, has an excellent electron injection effect for the light emitting layer or the light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also , A compound having excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

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

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

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

합성예Synthetic example

<합성예 1.> 화합물 IM-1의 합성<Synthesis Example 1.> Synthesis of Compound IM-1

1-bromonaphthalene-2,6-diol(SM-1, 20g), methyl acrylate (SM-2, 10.8g), tetrakis(triphenylphosphine)palladium(0)[tetrakis-(triphenylphosphine)palladium(0) ] (4.8 g), K ₂ CO ₃ (46 g) and anhydrous DMF (600 ml) was added to the flask under nitrogen atmosphere and heated to 110° C. and stirred for 12 hours. After the reaction is completed, it is cooled to room temperature, and nitrogen is replaced with hydrogen using a hydrogen balloon. The mixture was stirred at room temperature for 12 hours under a hydrogen atmosphere. After the reaction was completed, ethyl acetate and water were added, followed by separation, and the organic solvent layer was filtered by treatment with MgSO ₄ (anhydrous). The filtered solution was distilled off under reduced pressure and compound IM-1 (12.9 g) was obtained by column chromatography (eluent: CHCl ₃ /Hexane). As a result of the mass spectrum measurement of the obtained compound, a peak was confirmed at [M+H+]=247.

<합성예 2.> 화합물 IM-3 의 합성<Synthesis Example 2.> Synthesis of compound IM-3

Under a nitrogen atmosphere, the flask containing compound IM-1 and anhydrous THF (300 mL) was cooled to -40 °C, and then MeMgBr (3.0M in diethyl ether, 40 mL) was slowly added dropwise. After stirring at the same temperature for 30 minutes, it is further stirred at room temperature for 2 hours. When the reaction is over, sat at 0 °C. aq. NH ₄ Cl was slowly added dropwise and separated to collect only the organic layer and neutralized with aq.NaHCO ₃ . The organic solution was separated and then filtered by treatment with MgSO ₄ (anhydrous).

The flask obtained without further purification and the flask containing chloroform (300 mL) were cooled to 0°C, and then methane sulfonic acid (7 g) was slowly added dropwise. The flask was heated at 40°C and stirred for 5 hours. The reaction solution was cooled to room temperature, separated by adding water, and only the organic layer was collected and neutralized using aq.NaHCO ₃ . The organic solution was separated and then filtered by treatment with MgSO ₄ (anhydrous). The filtered solvent was removed under reduced pressure and purified by recrystallization (chloroform/hexane) to obtain compound IM-2 (7.6 g). As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=229.

Flask containing compound IM-2 (7.5 g), potassium carbonate (18.1 g), perfluorobutanesulfonyl fluoride (21.8 g) and acetonitrile (200 mL) and water (50 mL) Was stirred at room temperature for 2 hours. Distilled water (150 mL) was added, the mixture was further stirred at room temperature for 1 hour, and then the solid was filtered under reduced pressure. After dissolving the filtered solid in toluene, aq.NH ₄ Cl was added and separated, followed by MgSO ₄ (anhydrous) treatment to filter. The filtered solvent was removed under reduced pressure and purified by column chromatography to obtain compound IM-3 (19 g).

<합성예 3.> 화합물 A-1의 합성<Synthesis Example 3.> Synthesis of Compound A-1

Compound IM-3 (4g), N-(4-(tert-butyl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine (3.6g), bis(triphenylphosphine)palladium(0) The flask containing [bis(triphenylphosphine)palladium -(0)] (0.13g), cesium carbonate (5.8g) and xylene (30 ml) was heated at 140°C and stirred for 12 hours. The reaction solution was cooled to room temperature, separated by adding water and aq.NH ₄ Cl, and filtered by treatment with MgSO ₄ (anhydrous). The filtered solution was distilled off under reduced pressure and purified by silica gel column chromatography (developing solution: hexane/toluene) to obtain compound A-1 (2.7 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=876.

<합성예 4.> 화합물 A-2의 합성<Synthesis Example 4.> Synthesis of Compound A-2

Compound A-2 (3.3 g) was obtained by the same method as the method for synthesizing Compound A-1 of Synthesis Example 3. As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=947.

<합성예 5.> 화합물 A-3의 합성<Synthesis Example 5.> Synthesis of Compound A-3

Compound A-3 (2.9 g) was obtained by the same method as the method for synthesizing Compound A-1 of Synthesis Example 3. As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=835.

<합성예 6.> 화합물 IM-5의 합성<Synthesis Example 6.> Synthesis of compound IM-5

Compound IM-5 (21 g) was obtained using a phenylmagnesium bromide (1M in THF) solution in the same manner as the method for synthesizing compound IM-3 of Synthesis Example 2.

<합성예 7.> 화합물 B-1의 합성<Synthesis Example 7.> Synthesis of Compound B-1

Compound B-1 (2.4 g) was obtained by the same method as the method for synthesizing Compound A-1 of Synthesis Example 3. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=981.

<합성예 8.> 화합물 B-2의 합성<Synthesis Example 8.> Synthesis of Compound B-2

Compound B-2 (2.1 g) was obtained by the same method as the method for synthesizing Compound A-1 of Synthesis Example 3. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+] = 1035.

<합성예 9.> 화합물 IM-7의 합성<Synthesis Example 9.> Synthesis of compound IM-7

Compound IM-7 (16 g) was obtained by the same method as the method for synthesizing the compound IM-3 of Synthesis Example 2.

<합성예 10.> 화합물 C-1의 합성<Synthesis Example 10.> Synthesis of Compound C-1

Compound C-1 (1.8 g) was obtained by the same method as the method for synthesizing Compound A-1 of Synthesis Example 3. As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+] = 1034.

<합성예 11.> 화합물 C-2의 합성<Synthesis Example 11.> Synthesis of Compound C-2

Compound C-2 (2.3 g) was obtained by the same method as the method for synthesizing Compound A-1 of Synthesis Example 3. As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=895.

<실험예 1><Experimental Example 1>

HOMO of the molecule using the TD-DFT (B3LYP) method/6-31G* basis method. The energy levels of LUMO and singlet (S1) and the oscillator strength of singlet (radiation transition probability, f) were calculated. The calculation results are shown in Table 1 below.

	비교예1Comparative Example 1	비교예2Comparative Example 2	비교예 3Comparative Example 3	실시예 1Example 1
화합물compound	화합물 X-1Compound X-1	화합물 X-2Compound X-2	화합물 X-3Compound X-3	화합물 A-4Compound A-4
HOMOHOMO	4.574.57	4.714.71	4.834.83	4.704.70
LUMOLUMO	0.300.30	1.061.06	1.181.18	0.970.97
S1S1	3.933.93	3.173.17	3.183.18	3.213.21
ff	0.1610.161	0.1790.179	0.1340.134	0.2450.245

The radiative transition probability (f) is a measure of fluorescence quantum efficiency and is calculated by the following equation. The greater the value of the radiation transition probability (f), the greater the luminous efficiency.

The radiative transition probability (f) of Comparative Examples 1 to 3 obtained a very small value compared to Compound A-4 of Example 1, and as a result, the efficiency of the devices containing Compounds X-1 to X-3 would be very low. Can be expected In addition, the singlet energy value of Compound X-1 can be used to predict the emission wavelength, and since it is a very short wavelength compared to Compound A-4, the efficiency of the device is expected to be very low when used as a blue emission dopant in the light emitting layer, so it is an appropriate blue emission dopant. Can not.

Therefore, the luminous efficiency of Compound A-4 is higher than that of Compounds X-1, X-2, and X-3, and the efficiency of the blue light emitting device is also increased.

<실험예 2><Experimental Example 2>

실시예 2Example 2

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,500 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer Co. was used as a detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying, and then transported to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.

On the prepared ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum-deposited to a thickness of 500 Pa to form a hole injection layer.

(HAT)

A hole transport layer is vacuum-deposited by depositing 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (400 kPa) of the following formula, which is a material for transporting holes on the hole injection layer. Formed.

(NPB)

Subsequently, on the hole transport layer, a compound BH-A was vacuum-deposited to a thickness of 300 Pa as a light emitting layer host to form a light emitting layer. While depositing the light emitting layer, Compound A-1 was used as a blue light emitting dopant and 4% by weight compared to 100% of the total weight of the host.

An electron injection and transport layer was formed by vacuum-depositing Alq3 (aluminum tris(8-hydroxyquinoline)) of the following formula on the light emitting layer to a thickness of 200 Pa.

(Alq3)

On the electron injection and transport layer, lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 2,000 순차적 were sequentially deposited to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, the lithium fluoride of the negative electrode was maintained at a deposition rate of 0.3 Å/sec, and the aluminum was maintained at a deposition rate of 2 Å/sec, and the vacuum degree during deposition was 2×10. ^-7 to 5 x 10 ^-8 torr was maintained.

실시예 3 내지 11 및 비교예 4 내지 6.Examples 3 to 11 and Comparative Examples 4 to 6.

In Example 2, an organic light-emitting device was manufactured in the same manner as in Example 2, except that the dopant of the light-emitting layer and the host compound were used, respectively.

Table 2 shows the results of experiments of the organic light emitting device manufactured using each compound as a host and a dopant material at a current density of 20 mA/cm ² . The lifetime was measured to be 97% of the initial luminance (T97).

	호스트(발광층)Host (light emitting layer)	도펀트(발광층)Dopant (light emitting layer)	발광 효율(cd/A/y)Luminous efficiency (cd/A/y)	CIE(y)CIE(y)	수명T97Life T97
실시예 2Example 2	BH-ABH-A	A-1A-1	51.5 51.5	0.1 0.1	123.2 123.2
실시예 3Example 3	BH-ABH-A	A-3A-3	54.0 54.0	0.1 0.1	117.6 117.6
실시예 4Example 4	BH-ABH-A	B-1B-1	51.7 51.7	0.1 0.1	126.6 126.6
실시예 5Example 5	BH-BBH-B	A-2A-2	51.7 51.7	0.1 0.1	115.4 115.4
실시예 6Example 6	BH-BBH-B	C-1C-1	51.1 51.1	0.1 0.1	116.5 116.5
실시예 7Example 7	BH-CBH-C	B-2B-2	52.6 52.6	0.1 0.1	113.7 113.7
실시예 8Example 8	BH-CBH-C	C-2C-2	53.1 53.1	0.1 0.1	112.0 112.0
비교예 4Comparative Example 4	BH-ABH-A	X-3X-3	49.1 49.1	0.1 0.1	112.0 112.0
비교예 5Comparative Example 5	BH-CBH-C	X-3X-3	48.8 48.8	0.1 0.1	113.1 113.1
실시예 9Example 9	BH-DBH-D	A-1A-1	50.7 50.7	0.1 0.1	115.8 115.8
실시예 10Example 10	BH-DBH-D	B-2B-2	51.2 51.2	0.1 0.1	108.4 108.4
실시예 11Example 11	BH-DBH-D	C-2C-2	52.2 52.2	0.1 0.1	106.4 106.4
비교예 6Comparative Example 6	BH-DBH-D	X-3X-3	49.2 49.2	0.1 0.1	105.3 105.3

As shown in Table 2, the devices of Examples 2 to 11 using the compound having the structure of Formula 1 have higher efficiency and longer life characteristics than the devices of Comparative Examples 4 to 6.

Claims

Compound represented by the formula (1):

[Formula 1]

In Chemical Formula 1,

L1, L2 and L11 to L14 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R2 to R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n1 is an integer from 0 to 4, and when n1 is 2 or more, 2 or more R1s are the same 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,

The definitions of L1, L2, L11 to L14, Ar1 to Ar4, R1 to R7 and n1 are as defined in Chemical Formula 1.
The method according to claim 1,

Formula 1 is a compound represented by the following formula (4):

[Formula 4]

In Chemical Formula 4,

The definitions of L11 to L14, Ar1 to Ar4, R1 to R7 and n1 are as defined in Chemical Formula 1.
The method according to claim 1,

Formula 1 is a compound represented by the following formula (5):

[Formula 5]

In Chemical Formula 5,

The definitions of L1, L2, L11 to L14, Ar1 to Ar4, R1, R6, R7 and n1 are as defined in Formula 1 above.
The method according to claim 1,

Formula 1 is a compound represented by the following formula 6 or 7:

[Formula 6]

[Formula 7]

In Chemical Formulas 6 and 7,

The definitions of L1, L2, L11 to L14, Ar1 to Ar4, R1 and n1 are as defined in Formula 1 above,

R11 and R12 are the same as or different from each other, and each independently an substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

R13 and R14 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 cycloalkyl group having 3 to 30 carbon atoms; 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,

n13 and n14 are each an integer of 0 to 5, and when n13 and n14 are each 2 or more, the substituents in 2 or more parentheses are the same or different from each other.
The method according to claim 1,

Formula 1 is a compound represented by any one of the following compounds:

.
A first electrode; A second electrode; And at least one organic layer provided between the first electrode and the second electrode,

At least one layer of the organic layer comprises an organic light emitting device comprising a compound according to any one of claims 1 to 6.
The method according to claim 7,

The organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound.
The method according to claim 7,

The organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer includes the compound.
The method according to claim 7,

The organic material layer includes an emission layer, and the emission layer includes an organic light emitting device.
The method according to claim 7,

The organic material layer includes a light emitting layer, the light emitting layer is an organic light emitting device comprising the compound as a dopant of the light emitting layer.
The method according to claim 10,

The light emitting layer is an organic light emitting device that further comprises a compound represented by the formula H:

[Formula H]

In the formula H,

L21 to L23 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,

R21 to R27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a is 0 or 1,

Formula H may include one or more deuterium.