KR102274796B1 - Polycyclic compound and organic light emitting device comprising 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 {POLYCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0078167 submitted to the Korean Intellectual Property Office on July 05, 2018, the entire contents of which are incorporated herein by reference.

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

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 has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of 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.

The development of new materials for the organic light emitting device as described above is continuously required.

Korean Patent Publication No. 2015-076813

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,

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

Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

X is O, S or NR;

R and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

m1 is an integer from 0 to 7, and when m1 is 2 or more, R6 is the same as or different from each other,

R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R4 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with each other to form a substituted or unsubstituted ring,

n1 is an integer from 0 to 2, and when n1 is 2, R2 are the same as or different from each other,

n2 is an integer from 0 to 4, and when n2 is 2 or more, R3 is the same as or different from each other.

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

In particular, when the compound of the present invention is used in the hole injection layer, the hole transport layer or the electron suppression layer, the driving voltage of the device is lowered, the efficiency of the device is increased, and the lifespan is prolonged.

FIG. 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 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 did it
3 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (9), a light emitting layer (7), a hole blocking layer (10), electron transport and electron injection An example of an organic light emitting device connected to the layer 11 and the cathode 4 at the same time is shown.

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

The present specification provides a compound represented by the following formula (1). In the compound represented by the following formula (1), an amine group is substituted at a specific position of fluorene, and a dibenzofuran group at the position of R1; dibenzothiophene group; Alternatively, by including a carbazole group, the energy barrier with each organic layer may be controlled by controlling the HOMO and LUMO energy levels of the compound.

[Formula 1]

In Formula 1,

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

Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

X is O, S or NR;

R and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

m1 is an integer from 0 to 7, and when m1 is 2 or more, R6 is the same as or different from each other,

R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R4 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with each other to form a substituted or unsubstituted ring,

n1 is an integer from 0 to 2, and when n1 is 2, R2 are the same as or different from each other,

n2 is an integer from 0 to 4, and when n2 is 2 or more, R3 is the same as or different from each other.

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; halogen group; cyano group (-CN); nitro group; hydroxyl group; silyl group; boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted 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 biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

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

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

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

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 40 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, etc., but are not limited thereto.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C40. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like, but is not limited thereto. .

The substituents containing an alkyl group, an alkoxy group and other alkyl group moieties described herein include both straight-chain or pulverized forms.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- butenyl, 1,3-butadienyl, and the like, but are not limited thereto.

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, Si and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 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 a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group , a carbazole group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, and the like, but are not limited thereto.

In the present specification, the meaning of a “substituted or unsubstituted ring” formed by combining substituents with each other includes a substituted or unsubstituted aliphatic hydrocarbon ring by combining adjacent groups with each other; a substituted or unsubstituted aromatic hydrocarbon ring; substituted or unsubstituted aliphatic heterocycle; substituted or unsubstituted aromatic heterocycle; or they form a condensed ring.

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

In an exemplary embodiment of the present specification, X is O or S.

In an exemplary embodiment of the present specification, X is NR.

In an exemplary embodiment of the present specification, R and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted C 1 to C 40 alkyl group; a substituted or unsubstituted C 1 to C 40 alkoxy group; a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms; 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 an exemplary embodiment of the present specification, R is a substituted or unsubstituted aryl group.

According to another exemplary embodiment, R is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another exemplary embodiment, R is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, R is an aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, R is a substituted or unsubstituted phenyl group.

According to another exemplary embodiment, R is a phenyl group.

According to an exemplary embodiment of the present invention, R6 is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 40 alkyl group; 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, R6 is hydrogen; heavy 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 heterocyclic group having 2 to 30 carbon atoms.

In another exemplary embodiment, R6 is hydrogen.

According to an exemplary embodiment of the present specification, m1 is an integer of 0 to 2, and when m1 is 2, R6 is the same as or different from each other.

According to another exemplary embodiment, m1 is 0 or 1.

According to an exemplary embodiment of the present specification, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

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

According to another exemplary embodiment, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; or an arylene group having 6 to 30 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, L is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

In another exemplary embodiment, L is a direct bond; phenylene group; biphenylene group; or a naphthylene group.

In another exemplary embodiment, L is a direct bond; or a phenylene group.

In another exemplary embodiment, L is a direct bond.

In an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted triphenylenylene group; or a substituted or unsubstituted fluorenylene group.

In another exemplary embodiment, L1 and L2 are the same as or different from each other, and each independently a direct bond; phenylene group; biphenylene group; terphenylene group; naphthylene group; phenanthrenylene group; triphenylenylene group; dimethyl fluorenylene group; or a diphenylfluorenylene group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C 1 to C 40 alkyl group; a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms; 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, Ar1 and Ar2 are the same as or different from each other, and each independently 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.

In another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; an aryl group of 6 to 30; or a C 2 to C 30 heterocyclic group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

According to another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; phenyl group; biphenyl group; terphenyl group; naphthyl group; phenanthrenyl group; triphenylenyl group; dimethyl fluorenyl group; diphenylfluorenyl group; dibenzofuran group; dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as each other.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as each other and are a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as each other and are a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another exemplary embodiment, Ar1 and Ar2 are the same as each other, and 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 phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

In another exemplary embodiment, Ar1 and Ar2 are the same as each other, and a phenyl group; biphenyl group; terphenyl group; naphthyl group; phenanthrenyl group; triphenylenyl group; dimethyl fluorenyl group; diphenylfluorenyl group; dibenzofuran group; dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are different from each other.

In another exemplary embodiment, Ar1 and Ar2 are 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 phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

In another exemplary embodiment, Ar1 and Ar2 are different from each other, and each independently a phenyl group; biphenyl group; terphenyl group; naphthyl group; phenanthrenyl group; triphenylenyl group; dimethyl fluorenyl group; diphenylfluorenyl group; dibenzofuran group; dibenzothiophene group; or a carbazole group substituted with a phenyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are different from each other and are a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Ar1 and Ar2 are 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 phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; or a substituted or unsubstituted fluorenyl group.

In another exemplary embodiment, Ar1 and Ar2 are different from each other, and each independently a phenyl group; biphenyl group; terphenyl group; naphthyl group; phenanthrenyl group; triphenylenyl group; dimethyl fluorenyl group; or a diphenylfluorenyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are different from each other and are a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another exemplary embodiment, Ar1 and Ar2 are different from each other, and each independently a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

In another exemplary embodiment, Ar1 and Ar2 are different from each other, and each independently a dibenzofuran group; dibenzothiophene group; or a carbazole group substituted with a phenyl group.

In another exemplary embodiment, Ar1 and Ar2 are different from each other, and each independently a phenyl group; biphenyl group; terphenyl group; naphthyl group; phenanthrenyl group; triphenylenyl group; dimethyl fluorenyl group; diphenylfluorenyl group; dibenzofuran group; dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and Ar2 is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, 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 phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; or a substituted or unsubstituted fluorenyl group, wherein Ar2 is a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

According to an exemplary embodiment of the present specification, Ar1 is a phenyl group; biphenyl group; terphenyl group; naphthyl group; phenanthrenyl group; triphenylenyl group; dimethyl fluorenyl group; or a diphenylfluorenyl group, wherein Ar2 is a dibenzofuran group; dibenzothiophene group; or a carbazole group substituted with a phenyl group.

According to an exemplary embodiment of the present specification, Ar1 is a phenyl group; biphenyl group; phenanthrenyl group; triphenylenyl group; or a dimethyl fluorenyl group, wherein Ar2 is a dibenzofuran group; dibenzothiophene group; or a carbazole group substituted with a phenyl group.

According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted C 1 to C 40 alkyl group; a substituted or unsubstituted C 1 to C 40 alkoxy group; a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms; 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, R2 and R3 are the same as or different from each other and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to another exemplary embodiment, R2 and R3 are hydrogen.

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

According to another exemplary embodiment, n2 is 0 or 1.

According to an exemplary embodiment of the present specification, R4 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted C 1 to C 40 alkyl group; a substituted or unsubstituted C 1 to C 40 alkoxy group; a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms; a substituted or unsubstituted C 6 to C 60 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or combine with each other to form a substituted or unsubstituted C3 to C60 ring.

According to another exemplary embodiment, R4 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combine with each other to form a substituted or unsubstituted hydrocarbon ring.

In another exemplary embodiment, R4 and R5 are the same as or different from each other, and each independently a substituted or unsubstituted C1-C40 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or combined with each other to form a substituted or unsubstituted ring having 6 to 60 carbon atoms.

According to another exemplary embodiment, R4 and R5 are the same as or different from each other, and each independently a substituted or unsubstituted C1-C20 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with each other to form a substituted or unsubstituted fluorene ring.

In another exemplary embodiment, R4 and R5 are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group, or combined with each other to form a fluorene ring to form spirobifluorene.

In another exemplary embodiment, R4 and R5 are the same as or different from each other, and each independently a methyl group; Or a phenyl group, or combine with each other to form a fluorene ring to form spirobifluorene.

In another exemplary embodiment, R4 and R5 are the same as or different from each other, and each independently a methyl group; or a phenyl group.

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

The compound of Formula 1 of the present invention may have a core structure as shown in the following reaction scheme. 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.

<reaction formula>

Step 1)

Synthesis of bromine-substituted primary amine through bromination reaction of 2-fluorene amine and N-bromosuccinimide (NBS)

Step 2)

Synthesis of R1-L-substituted primary amine through Suzuki coupling reaction between bromine-substituted primary amine obtained in step 1 and R1-L-boronic acid

Step 3)

Synthesis of secondary amine through amination reaction of R1-L substituted primary amine obtained in step 2 and aryl halide (Ar1-L1-X1) (X1 = halide)

Step 4)

Synthesis of tertiary amine through amination reaction of secondary amine obtained in step 3 and aryl halide (Ar2-L2-X2) (X2 = halide)

In the above structural formula, R1 is a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In addition, in the present invention, the HOMO and LUMO energy levels of the compound can 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 invention includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by the above-described Chemical Formula 1.

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

The compound 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 invention 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 transport layer, a layer that transports and injects holes at the same time, an electron suppression layer, a light emitting layer, an electron transport layer and an electron injection layer, a layer that simultaneously transports and injects electrons. It may have a structure including the like. 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 diode of the present invention, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the above-described compound.

In the organic light emitting device of the present invention, the organic material layer may include a hole injection layer or a hole transport layer, the hole injection layer or 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 dopant of the emission layer.

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 of the light emitting layer, and may further include a host.

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 of the light emitting layer, a fluorescent host or a phosphorescent host, and another organic compound, a metal or a metal compound as a dopant may include

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.

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.

As another example, the organic material layer may include an emission layer, the emission layer may include the above-described compound as a host of the emission layer, and may further include a 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 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 blocking layer / electron transport layer / cathode

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

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

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

(15) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / layer for electron transport and electron injection at the same time / cathode

The structure of the organic light emitting device of the present invention may have the structure shown in FIGS. 1 to 3 , but is not limited thereto.

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

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

3 is an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light emitting layer 7, a hole blocking layer 10, electron transport and electron injection on the substrate 1 The structure of the organic light emitting device in which the layer 11 and the cathode 4 are sequentially stacked is illustrated. In such a structure, the compound may be included in the hole transport layer 6 or the electron blocking layer 9 .

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, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, a hole suppression layer, and a layer that simultaneously transports and injects electrons is formed thereon as a cathode It can be prepared by depositing a usable material. 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 includes a hole injection layer, a hole transport layer, a hole suppression layer, a layer that simultaneously injects and transports electrons, an electron suppression layer, a light emitting layer and an electron transport layer, an electron injection layer, a layer that simultaneously injects holes and transports holes, etc. It may have a multilayer structure, but is not limited thereto 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, and the hole injection material has the highest occupied (HOMO). 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 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 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 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.

The host material of the light emitting layer includes 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 compounds. 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.

A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and the hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, the hole-inhibiting material includes, but is not limited to, a triazine derivative, a phenanthroline derivative, and the like, and materials known in the art may be used.

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 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 with respect to 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. It is not limited to this.

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, an experimental example will be described in detail 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.

<Synthesis example>

Synthesis Example 1. Synthesis of compound 1

Step 1) Synthesis of compound 1-A

9,9'-dimethyl -9 H - fluorene-2-amine (50.00 g, 238.90 mmol) of N, N- dimethylformamide (DMF) was dissolved in (200 ml) was lowered to a temperature of 0 ℃. In the solution, N-bromosuccinimide (NBS) (42.52 g, 238.90 mmol) was dissolved in N,N-dimethylformamide (DMF) (150 ml), and then slowly added and stirred. After completion of the reaction, the temperature was raised to room temperature, and water was added to perform reverse precipitation, followed by filtration. The obtained solid was layer-separated with chloroform and sodium thiosulfate solution. After removal of the solvent, it was recrystallized from hexane to obtain Compound 1-A (58.50 g, 84.97 % yield).

Step 2) Synthesis of compound 1-B

Compound 1-A (58.5 g, 202.99 mmol) obtained in step 1 above and dibenzo[ b,d ]furan-4-ylboronic acid (45.19 g, 213.14 mmol) were dissolved in 1,4-dioxane (500 ml) After dissolution, a solution of potassium carbonate (84.17 g, 608.97 mmol: 250 ml of water) was added, followed by heating and stirring for 10 minutes. 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.45 g, 0.61 mmol) dissolved in 1,4-dioxane (20 ml) was added to the solution, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, the layers were separated with chloroform and water. After removal of the solvent, it was recrystallized from hexane to obtain the compound 1-B (61.5 g, 80.69 % yield).

Step 3) Synthesis of compound 1

Compound 1-B (20.0 g, 53.27 mmol), 4-bromo-1,1'-biphenyl (25.08 g, 107.61 mmol) obtained in step 2, and sodium tert-butoxide (14.33 g, 149.16 mmol) Toluene (250 ml) was added thereto, followed by heating and stirring for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.22 g, 0.43 mmol) dissolved in toluene (20ml) was added to the mixture, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, the layers were separated with toluene and water. After removal of the solvent, it was recrystallized from ethyl acetate to obtain Compound 1 (28.5 g, 78.69 % yield). (MS[M+H]+ = 680)

Synthesis Example 2. Synthesis of compound 2

Step 1) Synthesis of compound 2-A

Compound 1-B (40.0 g, 106.53 mmol), 4-bromo-1,1'-biphenyl (24.83 g, 106.53 mmol) obtained in step 2 of Synthesis Example 1, and sodium tert-butoxide (14.33 g) , 149.14 mmol) was added to toluene (350 ml), followed by heating and stirring for 10 minutes. 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.39 g, 0.53 mmol) dissolved in toluene (20ml) was added to the mixture, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, the layers were separated with chloroform and water. After removal of the solvent, it was recrystallized with ethyl acetate to obtain the compound 2-A (42.5 g, 75.61 % yield).

Step 2) Synthesis of compound 2

The compound obtained in the above step 1 2-A (20.0 g, 37.90 mmol), 2- bromo-9,9-dimethyl -9 H-fluorene (10.56 g, 38.66 mmol) and sodium tert-butoxide (5.10 g , 53.06 mmol) and toluene (200 ml) was added, followed by heating and stirring for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.097 g, 0.19 mmol) dissolved in toluene (20ml) was added to the mixture, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, the layers were separated with toluene and water. After removal of the solvent, the compound 2 (19.5 g, 71.47 % yield) was obtained by recrystallization with ethyl acetate. (MS[M+H]+ = 720)

Synthesis Example 3. Synthesis of compound 3

Step 2 of Synthesis Example 2 using Compound 2-A (20.0 g, 37.90 mmol) and 4-bromodibenzo[ b,d ]furan (9.55 g, 38.66 mmol) obtained in Step 1 of Synthesis Example 2 Compound 3 (19.8 g, 75.29 % yield) was obtained in the same manner as described above. (MS[M+H]+ = 694)

Synthesis Example 4. Synthesis of compound 4

Step 1) Synthesis of compound 4-A

The step of Synthesis Example 2 using Compound 1-B (40.0 g, 106.53 mmol) and 2-bromo-1,1'-biphenyl (24.83 g, 106.53 mmol) obtained in Step 2 of Synthesis Example 1 Compound 4-A (40.5 g, 72.05 % yield) was obtained in the same manner as in 1 above.

Step 2) Synthesis of compound 4

The compound 4-A obtained in the above step 1 (20.0 g, 37.90 mmol) and 2-bromo-9,9-dimethyl -9 H - fluorene (10.56 g, 38.66 mmol) the step of Synthesis Example 2 using Compound 4 (20.1 g, 73.67 % yield) was obtained in the same manner as in 2 above. (MS[M+H]+ = 720)

Synthesis Example 5. Synthesis of compound 5

Step 1) Synthesis of compound 5-A

Using the compound 1-B (40.0 g, 106.53 mmol) and 1-bromonaphthalene (22.06 g, 106.53 mmol) obtained in step 2 of Synthesis Example 1, in the same manner as in Step 1 of Synthesis Example 2, the compound 5-A (38.7 g, 72.42 % yield) was obtained.

Step 2) Synthesis of compound 5

Using the compound 5-A (20.0 g, 39.87 mmol) and 1-(4-bromophenyl)naphthalene (11.52 g, 40.67 mmol) obtained in step 1 above, in the same manner as in step 2 of Synthesis Example 2, Compound 5 (21.9 g, 78.04 % yield) was obtained. (MS[M+H]+ = 704)

Synthesis Example 6. Synthesis of compound 6

Step 1) Synthesis of compound 6-A

9,9'-diphenyl--9 H - fluorene-2-amine (50.00 g, 149.96 mmol) and N- bromo moseok shinny imide (NBS) step of the above Synthesis Example 1 using (26.69 g, 149.96 mmol) Compound 6-A (53.3 g, 86.20 % yield) was obtained in the same manner as in 1 above.

Step 2) Synthesis of compound 6-B

Using compound 6-A (53.3 g, 129.27 mmol) and dibenzo[ b,d ]furan-4-ylboronic acid (28.78 g, 135.73 mmol) obtained in step 1 above, step 2 of Synthesis Example 1 and Compound 6-B (52.5 g, 81.29 % yield) was obtained in the same manner.

Step 3) Synthesis of compound 6

The same method as in Step 3 of Synthesis Example 1 using Compound 1-B (20.0 g, 40.03 mmol) and 4-bromo-1,1'-biphenyl (18.85 g, 80.86 mmol) obtained in Step 2 above. to obtain the compound 6 (24.4 g, 75.81 % yield). (MS[M+H]+ = 804)

Synthesis Example 7. Synthesis of compound 7

Step 1) Synthesis of compound 7-A

Compound 7- in the same manner as in Step 1 of Synthesis Example 2 using Compound 6-B (40.0 g, 80.06 mmol) and bromobenzene (12.57 g, 80.06 mmol) obtained in Step 2 of Synthesis Example 6 A (38.0 g, 82.44 % yield) was obtained.

Step 2) Synthesis of compound 7

Using the compound 7-A (20.0 g, 34.74 mmol) and 2-bromotriphenylene (10.86 g, 35.43 mmol) obtained in step 1, in the same manner as in step 2 of Synthesis Example 2, compound 7 ( 21.5 g, 77.17 % yield) were obtained. (MS[M+H]+ = 802)

Synthesis Example 8. Synthesis of compound 8

Using compound 7-A (20.0 g, 34.74 mmol) and 9-(4-chlorophenyl)phenanthrene (10.23 g, 35.43 mmol) obtained in step 1 of Synthesis Example 7, step 2 of Synthesis Example 2 and Compound 8 (22.3 g, 77.52 % yield) was obtained in the same manner. (MS[M+H]+ = 828)

Synthesis Example 9. Synthesis of compound 9

Step 1) Synthesis of compound 9-A

The use of fluorene (21.87 g, 80.06 mmol) - The compound 6-B (40.0 g, 80.06 mmol) and 2-bromo -9,9'- dimethyl -9 H obtained in the above Synthesis Example 62 In the same manner as in Step 1 of Synthesis Example 2, the compound 9-A (46.0 g, 83.05 % yield) was obtained.

Step 2) Synthesis of compound 9

Using the compound 9-A (20.0 g, 28.91 mmol) and 9-(4-chlorophenyl)phenanthrene (8.51 g, 29.49 mmol) obtained in step 1, in the same manner as in step 2 of Synthesis Example 2, Compound 9 (22.8 g, 83.53 % yield) was obtained. (MS[M+H]+ = 944)

Synthesis Example 10. Synthesis of compound 10

Step 1) Synthesis of compound 10-A

Synthesis Example 1 using Compound 6-A (50.0 g, 121.26 mmol) obtained in Step 1 of Synthesis Example 6 and dibenzo[ b,d ]furan-1-ylboronic acid (26.99 g, 127.33 mmol) Compound 10-A (50.5 g, 83.36 % yield) was obtained in the same manner as in step 2.

Step 2) Synthesis of compound 10

The same method as in Step 3 of Synthesis Example 1 using Compound 10-A (20.0 g, 40.03 mmol) and 4-bromo-1,1'-biphenyl (18.85 g, 80.86 mmol) obtained in Step 1 above to obtain the compound 10 (23.4 g, 72.71 % yield). (MS[M+H]+ = 804)

Synthesis Example 11. Synthesis of compound 11

Step 1) Synthesis of compound 11-A

The use of fluorene (21.87 g, 80.06 mmol) - The compound 10-A (40.0 g, 80.06 mmol) and 2-bromo -9,9'- dimethyl -9 H obtained in the above Synthesis Example 10 1 Compound 11-A (44.0 g, 79.44 % yield) was obtained in the same manner as in Step 1 of Synthesis Example 2.

Step 2) Synthesis of compound 11

The same method as in Step 2 of Synthesis Example 2 using Compound 11-A (20.0 g, 28.91 mmol) and 4-bromo-1,1'-biphenyl (6.87 g, 29.49 mmol) obtained in Step 1 above. to obtain the compound 11 (19.0 g, 77.86 % yield). (MS[M+H]+ = 844)

Synthesis Example 12. Synthesis of compound 12

The step of Synthesis Example 2 using compound 11-A (20.0 g, 28.91 mmol) and 2-bromo-1,1'-biphenyl (6.87 g, 29.49 mmol) obtained in step 1 of Synthesis Example 1 Compound 12 (19.2 g, 78.68 % yield) was obtained in the same manner as in 2 above. (MS[M+H]+ = 844)

Synthesis Example 13. Synthesis of compound 13

Step 1) Synthesis of compound 13-A

Synthesis Example 1 using Compound 1-A (50.0 g, 173.50 mmol) obtained in Synthesis Example 1 Step 1 and dibenzo[ b,d ]thiophen-4-ylboronic acid (41.55 g, 182.18 mmol) Compound 13-A (57.5 g, 84.65 % yield) was obtained in the same manner as in step 2.

Step 2) Synthesis of compound 13-B

The same method as in Step 1 of Synthesis Example 2 using Compound 13-A (40.0 g, 102.16 mmol) and 4-bromo-1,1'-biphenyl (23.82 g, 102.16 mmol) obtained in Step 1 above. to give the compound 13-B (43.8 g, 78.85 % yield).

Step 3) Synthesis of compound 13

Using the compound 13-B (20.0 g, 36.78 mmol) and 2-bromotriphenylene (11.53 g, 37.52 mmol) obtained in step 2 above, in the same manner as in step 2 of Synthesis Example 2, compound 13 ( 22.8 g, 80.51 % yield) were obtained. (MS[M+H]+ = 770)

Synthesis Example 14. Synthesis of compound 14

Using compound 13-B (20.0 g, 36.78 mmol) and 9-(4-chlorophenyl)phenanthrene (10.83 g, 37.52 mmol) obtained in step 2 of Synthesis Example 13, step 2 of Synthesis Example 2 and Compound 14 (25.3 g, 86.41 % yield) was obtained in the same manner. (MS[M+H]+ = 796)

Synthesis Example 15. Synthesis of compound 15

Step 1) Synthesis of compound 15-A

The above Synthesis Example using Compound 6-A (50.0 g, 121.26 mmol) obtained in Step 1 of Synthesis Example 6 and dibenzo[ b,d ]thiophen-4-ylboronic acid (29.04 g, 127.33 mmol) Compound 15-A (51.2 g, 81.88 % yield) was obtained in the same manner as in Step 2 of 1.

Step 2) Synthesis of compound 15

The same method as in Step 3 of Synthesis Example 1 using Compound 15-A (20.0 g, 38.78 mmol) and 4-bromo-1,1'-biphenyl (18.26 g, 78.34 mmol) obtained in Step 1 above. to obtain the compound 15 (25.7 g, 80.81 % yield). (MS[M+H]+ = 820)

Synthesis Example 16. Synthesis of compound 16

Step 1) Synthesis of compound 16-A

Step 1 of Synthesis Example 2 using compound 15-A (40.0 g, 77.57 mmol) and 4-bromo-1,1'-biphenyl (18.08 g, 77.57 mmol) obtained in Synthesis Example 15 Step 1 Compound 16-A (40.3 g, 77.79 % yield) was obtained in the same manner as described above.

Step 2) Synthesis of compound 16

The same method as in Step 2 of Synthesis Example 2 using compound 16-A (20.0 g, 29.95 mmol) and 4-bromobenzo[ b,d ]thiophene (8.04 g, 30.54 mmol) obtained in step 1 above to obtain the compound 16 (20.0 g, 78.55 % yield). (MS[M+H]+ = 850)

Synthesis Example 17. Synthesis of compound 17

Step 1) Synthesis of compound 17-A

Synthesis Example 1 Using Compound 1-A (50.0 g, 173.50 mmol) and (9-phenyl-9H-carbazol-3-yl)boronic acid (52.31 g, 182.18 mmol) obtained in Synthesis Example 1 Step 1, the above Synthesis Example Compound 17-A (62.0 g, 79.30 % yield) was obtained in the same manner as in Step 2 of 1.

Step 2) Synthesis of compound 17

The same method as in Step 3 of Synthesis Example 1 using Compound 17-A (20.0 g, 44.39 mmol) and 4-bromo-1,1'-biphenyl (20.90 g, 89.66 mmol) obtained in Step 1 above. to give the compound 17 (26.2 g, 78.18 % yield). (MS[M+H]+ = 755)

Synthesis Example 18. Synthesis of compound 18

Step 1) Synthesis of compound 18-A

The step of Synthesis Example 2 using compound 17-A (40.0 g, 88.77 mmol) and 4-bromo-1,1'-biphenyl (21.11 g, 90.55 mmol) obtained in step 1 of Synthesis Example 17 Compound 18-A (40.0 g, 74.75 % yield) was obtained in the same manner as in 1 above.

Step 2) Synthesis of compound 18

The above synthesis example using compound 18-A (20.0 g, 33.18 mmol) obtained in step 1 and 4-bromo-1,1':4',1''-terphenyl (10.56 g, 33.84 mmol) Compound 18 (21.0 g, 76.16 % yield) was obtained in the same manner as in Step 2 of 2. (MS[M+H]+ = 831)

Synthesis Example 19. Synthesis of compound 19

1) Synthesis of compound 19-A

Synthesis Example 6 Using Compound 6-A (50.0 g, 121.26 mmol) and (9-phenyl-9H-carbazol-3-yl)boronic acid (36.56 g, 127.33 mmol) obtained in Synthesis Example 6 Step 1, the above Synthesis Example Compound 19-A (54.0 g, 77.48 % yield) was obtained in the same manner as in Step 2 of 1.

Step 2) Synthesis of compound 19

The same method as in Step 3 of Synthesis Example 1 using Compound 19-A (20.0 g, 34.80 mmol) and 4-bromo-1,1'-biphenyl (16.39 g, 70.29 mmol) obtained in Step 1 above. to give the compound 19 (23.8 g, 77.80 % yield). (MS[M+H]+ = 879)

Synthesis Example 20. Synthesis of compound 20

Step 1) Synthesis of compound 20-A

The step of Synthesis Example 2 using Compound 19-A (40.0 g, 69.60 mmol) and 4-bromo-1,1'-biphenyl (16.55 g, 70.99 mmol) obtained in Step 1 of Synthesis Example 19 Compound 20-A (38.0 g, 75.11 % yield) was obtained in the same manner as in 1 above.

Step 2) Synthesis of compound 20

Step 2 of Synthesis Example 2 using Compound 20-A (20.0 g, 27.51 mmol) and 2-bromo-9,9-dimethyl-9H-fluorene (7.67 g, 28.06 mmol) obtained in Step 1 Compound 20 (18.8 g, 74.35 % yield) was obtained in the same manner as described above. (MS[M+H]+ = 919)

Synthesis Example 21. Synthesis of compound 21

Step 1) Synthesis of compound 21-A

Compound 1-A (50.0 g, 173.50 mmol) obtained in step 1 of Synthesis Example 1 and (4-(dibenzo[ b,d ]furan-4yl)phenyl)boronic acid (52.49 g, 182.17 mmol) Compound 21-A (60.0 g, 76.58 % yield) was obtained in the same manner as in Step 2 of Synthesis Example 1 using the .

Step 2) Synthesis of compound 21

The same method as in Step 3 of Synthesis Example 1 using Compound 21-A (20.0 g, 44.29 mmol) and 4-bromo-1,1'-biphenyl (20.86 g, 89.47 mmol) obtained in Step 1 above to give the compound 21 (28.0 g, 83.63 % yield). (MS[M+H]+ = 756)

Synthesis Example 22. Synthesis of compound 22

Step 1) Synthesis of compound 22-A

Step 1 of Synthesis Example 2 using Compound 21-A (40.0 g, 88.58 mmol) and 4-bromo-1,1'-biphenyl (20.65 g, 88.58 mmol) obtained in Synthesis Example 21 Step 1 Compound 22-A (41.5 g, 77.61 % yield) was obtained in the same manner as described above.

Step 2) Synthesis of compound 22

Using the compound 22-A (20.0 g, 33.13 mmol) and 2-bromotriphenylene (10.38 g, 33.79 mmol) obtained in step 1 above, in the same manner as in step 2 of Synthesis Example 2, the compound 22 ( 21.5 g, 78.18 % yield) were obtained. (MS[M+H]+ = 830)

Synthesis Example 23. Synthesis of compound 23

Using compound 22-A (20.0 g, 33.13 mmol) and 9-(4-chlorophenyl)phenanthrene (9.76 g, 33.79 mmol) obtained in step 1 of Synthesis Example 22, step 2 of Synthesis Example 2 and Compound 23 (23.5 g, 82.86 % yield) was obtained in the same manner. (MS[M+H]+ = 856)

Synthesis Example 24. Synthesis of compound 24

Step 1) Synthesis of compound 24-A

Step 1 of Synthesis Example 2 using Compound 21-A (40.0 g, 88.58 mmol) and 4-bromo-1,1'-biphenyl (18.34 g, 88.58 mmol) obtained in Synthesis Example 21 Step 1 Compound 24-A (38.7 g, 75.62 % yield) was obtained in the same manner as described above.

Step 2) Synthesis of compound 24

Compound 24-A (20.0 g, 34.62 mmol) and 1-(4-bromophenyl)naphthalene (10.00 g, 35.31 mmol) obtained in Step 1 were used in the same manner as in Step 2 of Synthesis Example 2 above. Compound 24 (21.2 g, 78.51 % yield) was obtained. (MS[M+H]+ = 780)

<Experimental Examples and Comparative Experimental Examples>

Experimental Example 1-1

A glass substrate coated with ITO (Indium Tin Oxide) to a thickness of 1,400 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermal vacuum deposition of a compound represented by the following formula HAT on the prepared ITO transparent electrode to a thickness of 100 Å. After vacuum deposition of the compound represented by the following formula HT1 as a hole transport layer to a thickness of 1150 Å, the compound 1 prepared in Example 1 was thermally vacuum-deposited to a thickness of 150 Å as an electron suppression layer. Then, the compound represented by the following formula BH and the compound represented by the following formula BD as a light emitting layer were vacuum-deposited to a thickness of 200 Å in a weight ratio of 25:1. Then, as a hole blocking layer, a compound represented by the following formula HB1 was vacuum-deposited to a thickness of 50 Å. Subsequently, a compound represented by the following formula ET1 and a compound represented by the following Liq as a layer for simultaneously performing electron transport and electron injection were thermally vacuum deposited to a thickness of 310 Å in a weight ratio of 1:1. An organic light emitting device was manufactured by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1000 Å on the electron transport and electron injection layers to form a cathode.

Experimental Examples 1-2 to 1-21 and Comparative Experimental Examples 1-1 to 1-6

Experimental Examples 1-2 to 1-21 and Comparative Experimental Example 1-1 in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1 in Experimental Example 1-1. to 1-6 organic light emitting devices were manufactured. ^{When a current of 10 mA/cm 2} was applied to the organic light emitting diodes prepared in Experimental Examples and Comparative Experimental Examples, voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in Table 1 below. Meanwhile, T95 denotes a time required for the luminance to decrease from the initial luminance (6000 nits) to 95%.

electron suppression layer Voltage (V @ 10mA/cm ² ) Efficiency (cd/A @ 10mA/cm ² ) color coordinates (x, y) life span
(T95, hr) Experimental Example 1-1 compound 1 3.56 6.17 0.142, 0.044 290 Experimental Example 1-2 compound 3 3.53 6.16 0.141, 0.044 275 Experimental Example 1-3 compound 4 3.53 6.24 0.141, 0.045 280 Experimental Example 1-4 compound 6 3.55 6.24 0.141, 0.044 270 Experimental Example 1-5 compound 7 3.54 6.17 0.142, 0.045 270 Experimental Example 1-6 compound 8 3.50 6.13 0.141, 0.043 285 Experimental Example 1-7 compound 9 3.50 6.15 0.141, 0.043 285 Experimental Example 1-8 compound 10 3.52 6.10 0.140, 0.045 275 Experimental Example 1-9 compound 11 3.51 6.18 0.141, 0.043 285 Experimental Example 1-10 compound 12 3.55 6.21 0.139, 0.045 290 Experimental Example 1-11 compound 13 3.57 6.15 0.139, 0.044 280 Experimental Example 1-12 compound 14 3.52 6.19 0.142, 0.043 275 Experimental Example 1-13 compound 15 3.61 6.25 0.141, 0.043 275 Experimental Example 1-14 compound 16 3.60 6.18 0.139, 0.044 280 Experimental Example 1-15 compound 18 3.52 6.17 0.143, 0.044 290 Experimental Example 1-16 compound 19 3.62 6.24 0.141, 0.043 285 Experimental Example 1-17 compound 20 3.56 6.20 0.142, 0.044 275 Experimental Example 1-18 compound 21 3.63 6.24 0.143, 0.044 280 Experimental Example 1-19 compound 22 3.62 6.20 0.140, 0.044 285 Experimental Example 1-20 compound 23 3.55 6.20 0.141, 0.044 275 Experimental Example 1-21 compound 24 3.58 6.19 0.141, 0.043 290 Comparative Experimental Example 1-1 EB1 3.88 5.75 0.143, 0.046 235 Comparative Experimental Example 1-2 EB2 4.02 5.48 0.144, 0.048 205 Comparative Experimental Example 1-3 EB3 4.06 5.46 0.143, 0.047 210 Comparative Experimental Example 1-4 EB4 4.13 5.24 0.143, 0.048 185 Comparative Experimental Example 1-5 EB5 4.01 5.58 0.143, 0.046 200 Comparative Experimental Example 1-6 EB6 4.08 5.64 0.144, 0.048 205

As shown in Table 1, the compound of the present invention has excellent electron suppression ability, and it was confirmed that the organic light emitting device using the same as the electron suppression layer exhibits remarkable effects in terms of driving voltage, efficiency, and lifespan.

Specifically, Experimental Examples 1-1 to 1-21 in which a compound in which an amine group, a dibenzofuran group, a dibenzothiophene group, or a carbon position of a carbazole group is bonded to a specific position of fluorene is used in an electron suppression layer Compared to Examples 1-1 to 1-6, the driving voltage ^{was reduced up to about 0.42 (V@10mA/cm 2} ), the luminous efficiency was increased by up to about 20%, and the lifetime (T95) was increased by up to about 105 hr.

Experimental Examples 2-1 to 2-20 and Comparative Experimental Examples 1-1, 2-1 to 2-5

In Experimental Example 1-1, the compound represented by Formula EB1 was used instead of Compound 1 as the electron blocking layer, and the compound shown in Table 2 was used instead of the compound represented by Formula HT1 as the hole transport layer, except for using, Organic light emitting devices of Experimental Examples 2-1 to 2-20 and Comparative Experimental Examples 1-1 and 2-1 to 2-5 were manufactured in the same manner as in Experimental Example 1-1. ^{When a current of 10 mA/cm 2} was applied to the organic light emitting devices prepared in Experimental Examples and Comparative Experimental Examples, voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in Table 2 below. Meanwhile, T95 denotes a time required for the luminance to decrease from the initial luminance (6000 nits) to 95%.

hole transport layer Voltage (V @ 10mA/cm ² ) Efficiency (cd/A @ 10mA/cm ² ) color coordinates (x, y) life span
(T95, hr) Experimental Example 2-1 compound 1 3.55 6.18 0.142, 0.043 285 Experimental Example 2-2 compound 2 3.50 6.17 0.141, 0.043 275 Experimental Example 2-3 compound 3 3.54 6.24 0.142, 0.045 285 Experimental Example 2-4 compound 4 3.55 6.24 0.141, 0.044 270 Experimental Example 2-5 compound 5 3.52 6.18 0.141, 0.044 270 Experimental Example 2-6 compound 6 3.50 6.13 0.141, 0.043 285 Experimental Example 2-7 compound 9 3.52 6.18 0.142, 0.043 285 Experimental Example 2-8 compound 11 3.52 6.10 0.140, 0.045 280 Experimental Example 2-9 compound 12 3.51 6.19 0.142, 0.043 290 Experimental Example 2-10 compound 13 3.55 6.21 0.139, 0.044 295 Experimental Example 2-11 compound 14 3.55 6.15 0.140, 0.044 285 Experimental Example 2-12 compound 15 3.52 6.21 0.142, 0.045 275 Experimental Example 2-13 compound 16 3.60 6.25 0.139, 0.043 280 Experimental Example 2-14 chemical 17 3.52 6.20 0.142, 0.043 280 Experimental Example 2-15 compound 18 3.55 6.18 0.141, 0.044 290 Experimental Example 2-16 compound 20 3.54 6.25 0.141, 0.043 285 Experimental Example 2-17 compound 21 3.60 6.23 0.143, 0.043 280 Experimental Example 2-18 compound 22 3.62 6.20 0.141, 0.043 290 Experimental Example 2-19 compound 23 3.55 6.26 0.141, 0.044 275 Experimental Example 2-20 compound 24 3.59 6.19 0.141, 0.044 280 Comparative Experimental Example 1-1 HT1 3.88 5.75 0.143, 0.046 235 Comparative Experimental Example 2-1 HT2 4.01 5.44 0.144, 0.047 200 Comparative Experimental Example 2-2 HT3 4.06 5.45 0.144, 0.048 215 Comparative Experimental Example 2-3 HT4 4.14 5.25 0.144, 0.047 180 Comparative Experimental Example 2-4 HT5 4.00 5.35 0.144, 0.047 190 Comparative Experimental Example 2-5 HT6 4.11 5.40 0.144, 0.048 195

As shown in Table 2, the compound of the present invention has excellent electron suppression ability, and it was confirmed that the organic light emitting device using the same as a hole transport layer exhibited remarkable effects in terms of driving voltage, efficiency, and lifespan.

Specifically, Experimental Examples 2-1 to 2-20 in which a compound in which an amine group and a dibenzofuran group, a dibenzothiophene group or a carbon position of a carbazole group are bonded to a specific position of fluorene in a hole transport layer are Comparative Experimental Examples Compared to 1-1, 2-1 to 2-5, the driving voltage is ^{reduced by up to about 0.64 (V@10mA/cm 2} ), the luminous efficiency is increased by up to about 20%, and the lifespan (T95) is up to about 110 hr increased.

1: substrate
2: Anode
3: light emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: light emitting layer
8: electron transport layer
9: Electron suppression layer
10: hole blocking layer
11: A layer that simultaneously transports electrons and injects electrons

Claims (7)

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

In Formula 1,
L, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
X is O, S or NR;
R and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
m1 is an integer from 0 to 7, and when m1 is 2 or more, R6 is the same as or different from each other,
R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R4 and R5 are the same as or different from each other, and each independently an alkyl group or an aryl group,
n1 is an integer from 0 to 2, and when n1 is 2, R2 are the same as or different from each other,
n2 is an integer from 0 to 4, and when n2 is 2 or more, R3 is the same as or different from each other. The method according to claim 1,
L is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group. The method according to claim 1,
R4 and R5 are the same as or different from each other, and each independently an alkyl group having 1 to 40 carbon atoms; Or a compound that is an aryl group having 6 to 60 carbon atoms. 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 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 the compound according to any one of claims 1 to 4 . 6. The method of claim 5,
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. 6. The method of claim 5,
The organic material layer includes an electron blocking layer, and the electron blocking layer is an organic light emitting device comprising the compound.

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