KR20200096172A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound represented by chemical formula 1 and an organic light emitting device comprising the same. The organic light emitting device using the compound has a low driving voltage.

Description

A compound and an organic light emitting device containing the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2019-0013530, filed with the Korean Intellectual Property Office on February 01, 2019, all of which is included in this specification.

The present application relates to a compound and an organic light emitting device comprising the same.

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 a first electrode, a second electrode, and an organic material layer therebetween. Here, the organic material layer is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected in the first electrode and electrons are injected in the organic material layer in the second electrode, and excitons are formed when the injected holes meet the electrons. , When this exciton falls back to ground, it glows.

The development of new materials for such organic light-emitting devices continues to be required.

Korean Patent Publication No. 10-2011-0107681

It is to provide the compound of the present application and an organic light emitting device including the same.

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

[Formula 1]

In Chemical Formula 1,

R1 to R4 are each independently hydrogen; Or deuterium,

R5 and R6 are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a is an integer from 0 to 6,

b and d are each independently an integer from 0 to 4,

c is an integer from 0 to 2,

When a to d are each independently, 2 or more, the substituents in parentheses are the same as or different from each other,

When b to d are each independently 2 or more, two or more R 2 to R 4 may be independently bonded to adjacent substituents to form a ring.

In addition, the present application is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, and at least one layer of the organic material layer provides an organic light emitting device comprising the above-described compound.

The organic light-emitting device using the compound according to the exemplary embodiment of the present application is capable of low driving voltage, high luminous efficiency, or long life.

1 shows an example of an organic light emitting device in which a substrate 1, a first electrode 2, a light emitting layer 3, and a second electrode 4 are sequentially stacked.
2 shows a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injection and An example of an organic light-emitting device in which the transport layer 9 and the second electrode 4 are sequentially stacked is shown.

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

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

According to the exemplary embodiment of the present application, the compound represented by Chemical Formula 1 has an advantage of controlling triplet energy by having the core structure as described above, and can exhibit characteristics of long life and high efficiency.

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 the present specification is hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And substituted or unsubstituted heterocyclic groups, substituted with 1 or 2 or more substituents selected from the group, or substituted with 2 or more substituents among the exemplified substituents, or having no substituents. For example, "a substituent to 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 to which two phenyl groups are connected.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

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 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, 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, specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto. Does not.

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. 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, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, steelbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 24 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

및

등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

And

And the like, but is not limited thereto.

In the present specification, the heterocyclic group includes one or more non-carbon atoms, heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms of the heterocyclic group is not particularly limited, but it is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, Isooxazolyl groups, oxadiazolyl groups, thiadiazolyl groups, benzothiazolyl groups, phenothiazinyl groups and dibenzofuranyl groups, and the like, but are not limited thereto.

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

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

In the present specification, the amine group is -NH ₂ ; Alkylamine groups; N-alkylarylamine group; Arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group are methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine Group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, and the like, but is not limited thereto.

In the present specification, the N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, an alkylamine group; N-alkylarylamine group; Arylamine group; N-aryl heteroarylamine group; The alkyl group, the aryl group, and the heteroaryl group in the N-alkyl heteroarylamine group and the heteroarylamine group, respectively, the description of the above-described alkyl group, aryl group and heteroaryl group can be applied.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. Can. For example, two substituents substituted at the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the meaning that adjacent groups combine with each other to form a ring means that adjacent groups combine with each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heteroring, as described above. Or it may form a polycyclic, may be aliphatic, aromatic, or a condensed form thereof, and is not limited thereto.

In the present specification, the meaning of forming a ring by bonding with adjacent groups to form a ring is a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means that they form a combined form.

In the present specification, the aliphatic hydrocarbon ring refers to a ring that is not aromatic and consists only of carbon and hydrogen atoms.

In the present specification, examples of the aromatic hydrocarbon ring include a phenyl group, a naphthyl group, anthracenyl group, and the like, but are not limited thereto.

In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms.

In the present specification, an aromatic heterocycle means an aromatic ring containing one or more of heteroatoms.

The compound represented by Formula 1 is selected from any one of Formulas 2 to 4 below.

[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4, R1 to R6 and a to d are as defined in Formula 1.

According to an exemplary embodiment of the present application, R1 to R4 are each independently hydrogen; Or it may be deuterium, or it may combine with adjacent groups to form a ring.

According to an exemplary embodiment of the present application, R1 to R4 are hydrogen.

According to an exemplary embodiment of the present application, R1 to R4 may be combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring.

According to an exemplary embodiment of the present application, when b to d are each independently 2 or more, two or more R2 to R4 may be independently bonded to each other to form a ring.

According to an exemplary embodiment of the present application, when b is 2 or more, two or more R2 may combine with adjacent groups to form a ring.

According to an exemplary embodiment of the present application, when b is 2 or more, two or more R 2 may be bonded to each other adjacent to each other to form a substituted or unsubstituted benzene ring.

According to an exemplary embodiment of the present application, when b is 2 or more, two or more R2 may be bonded to groups adjacent to each other to form a benzene ring.

According to an exemplary embodiment of the present application, when c is 2 or more, two or more R3 may combine with each other adjacent groups to form a ring.

According to an exemplary embodiment of the present application, when c is 2 or more, two or more R3 may combine adjacent groups to form a benzene ring.

According to an exemplary embodiment of the present application, when d is 2 or more, two or more R4 may combine adjacent groups to each other to form a ring.

According to an exemplary embodiment of the present application, when d is 2 or more, two or more R4 may combine adjacent groups to each other to form a benzene ring.

The compound represented by Chemical Formula 1 is selected from any one of the following Chemical Formulas 2-1 to 2-8, 3-1 to 3-8, and 4-1 to 4-8.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

[Formula 2-8]

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

[Formula 3-5]

[Formula 3-6]

[Formula 3-7]

[Chemical Formula 3-8]

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

[Formula 4-4]

[Formula 4-5]

[Formula 4-6]

[Formula 4-7]

[Formula 4-8]

In Formulas 2-1 to 2-8, 3-1 to 3-8, and 4-1 to 4-8, R4 to R6 and d are as defined in Formula 1,

R7 and R8 are each independently hydrogen; Or deuterium,

e1 and e2 are 0 or 1, respectively, and the sum of e1 and e2 is 1 to 2,

e is an integer from 0 to 10, f is an integer from 0 to 8,

When e is 2 or more, a plurality of R7s are the same as or different from each other,

When f is 2 or more, a plurality of R8s are the same or different from each other.

According to an exemplary embodiment of the present application, R5 and R6 are each independently, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

According to an exemplary embodiment of the present application, R5 and R6 are each independently, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

According to an exemplary embodiment of the present application, R5 and R6 are each independently, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present application, R5 and R6 are each independently, a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted dibenzofuran group.

According to an exemplary embodiment of the present application, R5 and R6 are each independently, a phenyl group; Naphthyl group; Biphenyl group; Phenanthrene group; A carbazole group unsubstituted or substituted with a phenyl group; Dibenzothiophene group; Or dibenzofuran group.

Further, according to an exemplary embodiment of the present specification, the compound represented by Formula 1 is any one selected from the following structural formulas.

In addition, the present specification provides an organic light emitting device comprising the above-described compound.

In one embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, and at least one of the organic material layers includes the compound.

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

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 specifically stated otherwise.

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 may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer as an organic material layer. However, the structure of the organic light emitting device is not limited to this, and may include fewer organic layers.

In one embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or hole transport layer includes the compound.

In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer contains the compound.

In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer contains the compound as a host.

In one embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes a compound of Formula 1 as a first host, and further includes a second host represented by Formula H below.

[Formula H]

In Formula H,

A is a substituted or unsubstituted naphthalene ring,

Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms,

L1 to L3 are each independently a single bond; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms,

Ar2 and Ar3 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms containing at least one heteroatom of N, O and S,

p is an integer from 0 to 9.

In one embodiment of the present specification, A is a substituted or unsubstituted naphthalene ring.

In the exemplary embodiment of the present specification, A is a naphthalene ring unsubstituted or substituted with deuterium.

In one embodiment of the present specification, A is a naphthalene ring.

In one embodiment of the present specification, p denotes the number of deuterium substitutions, and when p is 0, all denote hydrogen.

In one embodiment of the present specification, L1 to L3 are each independently, a single bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L1 to L3 are each independently, a single bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthalene group.

In one embodiment of the present specification, L1 to L3 are each independently, a single bond; A phenylene group unsubstituted or substituted with deuterium; Or a naphthalene group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, L1 to L3 are each independently, a single bond; Phenylene group; Or it is a naphthalene group.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one 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; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with a group selected from the group consisting of deuterium, an alkyl group, a cycloalkyl group, and an aryl group; A biphenyl group unsubstituted or substituted with a group selected from the group consisting of deuterium, alkyl groups, cycloalkyl groups, and aryl groups; A terphenyl group unsubstituted or substituted with a group selected from the group consisting of deuterium, alkyl group, cycloalkyl group, and aryl group; Or a naphthyl group unsubstituted or substituted with a group selected from the group consisting of deuterium, an alkyl group, a cycloalkyl group, and an aryl group.

In one embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with a group selected from the group consisting of deuterium, an alkyl group, a cycloalkyl group, and an aryl group; Biphenyl group; Terphenyl group; Or a naphthyl group.

In the exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with a group selected from the group consisting of deuterium, tertbutyl group, adamantyl group, phenyl group, and naphthyl group; Biphenyl group; Terphenyl group; Or a naphthyl group.

In one embodiment of the present specification, Ar2 and Ar3 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms containing at least one heteroatom of N, O and S.

In one embodiment of the present specification, Ar2 and Ar3 are 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 fluorenyl group; A substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.

In the exemplary embodiment of the present specification, Ar2 and Ar3 are each independently a phenyl group unsubstituted or substituted with a group selected from the group consisting of deuterium, alkyl group, cycloalkyl group, and aryl group; A biphenyl group unsubstituted or substituted with deuterium; Terphenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with deuterium; A fluorenyl group unsubstituted or substituted with an alkyl group; A dibenzofuranyl group unsubstituted or substituted with deuterium; Or a dibenzothiophenyl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar2 and Ar3 are each independently a phenyl group unsubstituted or substituted with a group selected from the group consisting of deuterium, tertbutyl group, ammantyl group, and phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Dimethylfluorenyl group; Dibenzofuranyl group; Or a dibenzothiophenyl group.

In one embodiment of the present specification, the second host represented by Chemical Formula H may be represented by any one of the following structures, but is not limited thereto.

.

.

In one embodiment of the present specification, 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.

In one embodiment of the present specification, the organic light emitting device is a hole injection layer, a hole transport layer. It further includes one or two or more layers selected from the group consisting of an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

In one embodiment of the present application, the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. It includes two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, and at least one of the two or more organic material layers contains the compound. In the exemplary embodiment of the present application, two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and injects electrons, and a hole blocking layer.

In another exemplary embodiment, the organic light emitting device may be an organic light emitting device having a structure in which a first electrode, one or more organic material layers, and a second electrode are sequentially stacked on a substrate.

In another exemplary embodiment, the organic light emitting device may be an organic light emitting device of an inverted type in which a second electrode, one or more organic material layers, and a first electrode are sequentially stacked on a substrate.

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/Anode

(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 blocking layer/light emitting layer/electron transport layer/cathode

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

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

(10) Anode/hole injection layer/hole transport layer/electron blocking 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/Anode

(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/electron transport layer/electron injection layer/cathode

(16) Anode/Hole injection layer/Hole transport layer/Electron blocking layer/Light emitting layer/Hole blocking layer/Electron transport and injection layer/Anode

For example, the structure of the organic light emitting device according to the exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2.

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

2 shows a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, electron injection and The structure of the organic light emitting device in which the transport layer 9 and the second electrode 4 are sequentially stacked is illustrated. In such a structure, the compound is selected from among the hole injection layer 5, the hole transport layer 6, the electron blocking layer 7, the light emitting layer 3, the hole blocking layer 8, and the electron injection and transport layer 9 May be included on the first floor or higher. In such a structure, the compound may be included in the emission layer 3.

The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound of the present specification, that is, the compound.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

The organic light emitting device of the present specification may be made of materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Formula 1.

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a first electrode is obtained by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. And forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a second electrode thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing the organic light emitting device. Here, the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

In addition to such a method, an organic light emitting device may be made by sequentially depositing an organic material layer and a first electrode material from a second electrode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

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

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

As the first electrode material, a material having a large work function is generally preferable to facilitate hole injection into the organic material layer. Specific examples of the first 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); ZnO:Al or SnO ₂ : combination of metal and oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

The second electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the second 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 injects holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect in the first electrode, an excellent hole injection effect in the light emitting layer or the light emitting material. A compound that prevents the movement of the generated excitons to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the first electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, 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 hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. As a hole transport material, the hole is transported to the light emitting layer by transporting holes from the first electrode or the hole injection layer to the light emitting layer. This large material is suitable. 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 blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may be a material known in the art.

The light emitting layer may include a host material and a dopant material. The host material includes the compound of Formula 1 herein, and may further include 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, and the like, and heterocyclic compounds include carbazole derivatives, dibenzofuran, and dibenzofuran Derivatives, dibenzothiophene, dibenzothiophene derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

The dopant material includes the following compounds, but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the second electrode and transferring them to the light emitting layer, a material having high mobility for electrons This is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specifically, they are cesium, barium, calcium, ytterbium and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a second electrode, an excellent electron injection effect on a light emitting layer or a light emitting material, and excitons generated in the light emitting layer A compound that prevents migration to the hole injection layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene 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, 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 hole blocking layer is a layer that blocks the arrival of the second electrode 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 organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

Hereinafter, the present specification will be described in more detail through examples. However, the following examples are for illustrative purposes only and are not intended to limit the specification.

The compound according to the present specification was prepared using a Buchwald-Hartwig coupling reaction, a Heck coupling reaction, and a Suzuki coupling reaction as representative reactions.

[Production Example 1] Preparation of formula a(5H-benzo[b]carbazole)

1) Preparation of formula a-1

Naphthalen-2-amine 300.0 g (1.0 eq), 1-bromo-2-iodobenzene 592.7 g (1.0 eq), NaOtBu 302.0 g (1.5 eq), palladium acetate (Pd(OAc) ₂ ) 4.70 g (0.01 eq), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (4,5-Bis(diphenylphosphino)-9,9 -Dimethylxanthene, Xantphos) dissolved in 12.12 g (0.01 eq) and 5 L of 1,4-dioxane (1,4-dioxane) and stirred under reflux. When the reaction was completed after 3 hours, the solvent was removed under reduced pressure. After that, it was completely dissolved in ethyl acetate (Ethylacetate), washed with water, and then reduced again to remove about 70% of the solvent. Hexane was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 443.5 g of compound a-1 (yield 71%). [M+H]+=299

2) Preparation of formula a(5H-benzo[b]carbazole)

Formula a-1 443.5 g (1.0 eq), Pd(t-Bu ₃ P) ₂ 8.56 g (0.01 eq) and K ₂ CO ₃ 463.2 g (2.00 eq) were added to 4 L of diethylacetamide (DMAC) It was refluxed and stirred. After 3 hours, the reaction was poured into water, crystals were dropped and filtered. The filtered solid was completely dissolved in 1,2-dichlorobenzene (1,2-dichlorobenzene), washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure. This was purified by column chromatography to obtain 174.8 g (yield 48%) of formula a(5H-benzo[b]carbazole). [M+H]+=218

Here, tBu means tertbutyl.

[Production Example 2] Preparation of formula b(7H-dibenzo[b,g]carbazole)

Using 1-bromo-2-iodonaphthalene instead of 1-bromo-2-iodonaphthalene, the formula b (7H-dibenzo[b) was used in the same manner as the preparation method of formula a. ,g]carbazole) was synthesized. [M+H]+=268

[Production Example 3] Preparation of formula c(6H-dibenzo[b,h]carbazole)

Formula c(6H-dibenzo[b,h]carbazole in the same manner as in the method of formula a using 2,3-dibromonaphthalene instead of 1-bromo-2-idodobenzene. ). [M+H]+=268

[Production Example 4] Preparation of chemical formula d (13H-dibenzo[a,h]carbazole)

Using 2-bromo-1-iodonaphthalene instead of 1-bromo-2-idodobenzene, the formula d(13H-dibenzo[a ,h]carbazole). [M+H]+=268

[Production Example 5] Preparation of formula e

1) Preparation of formula e-3

1-bromo-2-chloro-3-iodobenzene 200.0 g (1.0 eq), (2-(methylthio)phenyl)boronic acid 105.9 g (1.0 eq), K ₂ CO ₃ 173.9 g (2.0 eq) and Pd (PPh ₃ ) ₄ (Tetrakis(triphenylphosphine)palladium(0)) 14.55 g (0.02 eq) was dissolved in 3 L of tetrahydrofuran (THF) and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that, it was completely dissolved in Ethylacetate, washed with water, and then reduced again to remove the solvent by about 80%. Hexane was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 138.36 g of compound e-3 (70% yield). [M+H]+=312

2) Preparation of formula e-2

Formula e-3 138.36 g (1.0 eq) and H ₂ O ₂ 22.5 g (2.00 eq) were added to 1 L of acetic acid (AcOH), followed by reflux and stirred. After 1 hour, the reaction was poured into water to drop crystals and filtered. The filtered solid was completely dissolved in Ethylacetate, washed with water, and then reduced again to remove about 80% of the solvent. Hexane was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 91.61 g of compound e-2 (63% yield). [M+H]+=328

3) Preparation of Formula e-1

Formula e-2 91.61 g (1.0 eq), 500 ml of H ₂ SO _{4 was} added, refluxed and stirred while being dissolved. When the reaction was completed after 2 hours, the reaction product was poured into water to drop crystals and filtered. The filtered solid was completely dissolved in CHCl ₃ , washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure to remove about 80% of the solvent. Hexane was added again under reflux, the crystals were dropped and cooled, and then column chromatography was performed to obtain 50.45 g of chemical formula e-1 (yield 61%). [M+H]+=296

3) Preparation of formula e

Formula e-1 50.45 g (1.0 eq), Bis(pinacolato)diboron 55.96 g (1.3 eq), Pd(dppf)Cl ₂ 2.48g (0.02 eq), KOAc 18.98 g (2.00 eq) into dioxnae 800 mL and reflux And stirred. When the reaction was completed after 3 hours, the solvent was removed under reduced pressure. The filtered solid was completely dissolved in CHCl ₃ , washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure to remove about 90% of the solvent. This was added to ethanol again under reflux, the crystals were dropped, cooled, and filtered to obtain the formula e 49.66 g (yield 84%). [M+H]+=345

[Production Example 6] Preparation of formula f

Formula f was synthesized by using 2-bromo-1-chloro-4-iodobenzene instead of 1-bromo-2-chloro-3-iodobenzene in the same manner as in formula e. [M+H]+=345

[Production Example 7] Preparation of formula g

Formula g was synthesized in the same manner as in the formula e using 1-bromo-3-chloro-5-iodobenzene instead of 1-bromo-2-chloro-3-iodobenzene. [M+H]+=345

[Production Example 8] Preparation of formula h

Instead of (2-(methylthio)phenyl)boronic acid, (3-(methylthio)naphthalen-2-yl)boronic acid was used to synthesize the formula h in the same manner as the preparation method of formula e. [M+H]+=395

[Production Example 9] Preparation of formula (i)

Instead of (2-(methylthio)phenyl)boronic acid, (3-(methylthio)naphthalen-2-yl)boronic acid was used to synthesize Chemical Formula i in the same manner as in the preparation method of Chemical Formula f. [M+H]+=395

[Preparation Example 10] Preparation of Formula j

(3-(methylthio)naphthalen-2-yl)boronic acid was used instead of (2-(methylthio)phenyl)boronic acid to synthesize formula j in the same manner as in formula g. [M+H]+=395

[Production Example 11] Preparation of formula k

Formula (k) was synthesized in the same manner as in the formula (e) using (1-(methylthio)naphthalen-2-yl)boronic acid instead of (2-(methylthio)phenyl)boronic acid. [M+H]+=395

[Production Example 12] Chemical Formula l Production

Formula (h) was synthesized in the same manner as in the method of formula (f) using (1-(methylthio)naphthalen-2-yl)boronic acid instead of (2-(methylthio)phenyl)boronic acid d. [M+H]+=395

[Production Example 13] Preparation of formula m

(2-(methylthio)phenyl)boronic acid was used instead of (1-(methylthio)naphthalen-2-yl)boronic acid to synthesize formula m in the same manner as in formula g. [M+H]+=395

[Production Example 14] Preparation of Formula n

(2-(methylthio)phenyl)boronic acid was used instead of (2-(methylthio)naphthalen-1-yl)boronic acid to synthesize Formula n in the same manner as in Formula e. [M+H]+=395

[Production Example 15] Preparation of formula o

(2-(methylthio)phenyl)boronic acid instead of (2-(methylthio)naphthalen-1-yl)boronic acid was used to synthesize the formula o in the same manner as in the formula f. [M+H]+=395

Preparation Example 15 Formula p Preparation

(2-(methylthio)phenyl)boronic acid was used instead of (2-(methylthio)naphthalen-1-yl)boronic acid to synthesize formula p in the same manner as in formula g. [M+H]+=395

Using the intermediates synthesized in Preparation Examples 1 to 15, an intermediate containing triazine was proceeded through a Suzuki coupling reaction, and the compounds of the following synthesis examples were synthesized.

Synthesis Example 1

In a nitrogen atmosphere, sub1 (10 g, 19 mmol), formula a (4.5 g, 20.9 mmol) and sodium tert-butoxide (NaOtBu, sodium tert-butoxide) (3.7 g, 38 mmol) were added to 200 ml of Xylene and stirred and Refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (Pd (t-Bu ₃ P) ₂ , bis (tri-tert-butylphosphine) palladium (0)) (0.2 g, 0.4 mmol) was added. . After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 1 (9.4 g). (Yield 70%, MS: [M+H] + =707)

Synthesis Example 2

In a nitrogen atmosphere, sub2 (10 g, 18.2 mmol), chemical formula a (4.3 g, 20 mmol) and sodium tert-butoxide (3.5 g, 36.4 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 2 (7.4 g). (Yield 56%, MS: [M+H] + = 731)

Synthesis Example 3

In a nitrogen atmosphere, sub3 (10 g, 16.7 mmol), formula a (4 g, 18.3 mmol) and sodium tert-butoxide (3.2 g, 33.3 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 3 (7.3 g). (Yield 56%, MS: [M+H] + = 781)

Synthesis Example 4

In a nitrogen atmosphere, sub4 (10 g, 15.1 mmol), chemical formula a (3.6 g, 16.6 mmol), and sodium tert-butoxide (2.9 g, 30.2 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 4 (8.6 g). (Yield 68%, MS: [M+H] + = 843)

Synthesis Example 5

In a nitrogen atmosphere, sub5 (10 g, 15.9 mmol), chemical formula a (3.8 g, 17.5 mmol) and sodium tert-butoxide (3.1 g, 31.8 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 5 (7.8 g). (Yield 61%, MS: [M+H]+= 810)

Synthesis Example 6

In a nitrogen atmosphere, sub6 (10 g, 22.2 mmol), formula a (5.3 g, 24.4 mmol) and sodium tert-butoxide (4.3 g, 44.4 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 6 (7.1 g). (Yield 51%, MS: [M+H]+= 631)

Synthesis Example 7

In a nitrogen atmosphere, sub7 (10 g, 18.2 mmol), formula a (4.3 g, 20 mmol) and sodium tert-butoxide (3.5 g, 36.4 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 7 (9.2 g). (Yield 69%, MS: [M+H] + = 731)

Synthesis Example 8

In a nitrogen atmosphere, sub8 (10 g, 15.4 mmol), formula a (3.7 g, 16.9 mmol) and sodium tert-butoxide (3 g, 30.8 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 8 (6.6 g). (Yield 52%, MS: [M+H] + = 831)

Synthesis Example 9

In a nitrogen atmosphere, sub9 (10 g, 16.5 mmol), formula a (3.9 g, 18.1 mmol) and sodium tert-butoxide (3.2 g, 33 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 9 (8.4 g). (Yield 65%, MS: [M+H]+= 787)

Synthesis Example 10

In a nitrogen atmosphere, sub10 (10 g, 14.5 mmol), chemical formula a (3.5 g, 15.9 mmol) and sodium tert-butoxide (2.8 g, 28.9 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 10 (7.6 g). (Yield 60%, MS: [M+H] + = 872)

Synthesis Example 11

In a nitrogen atmosphere, sub11 (10 g, 20 mmol), chemical formula a (4.8 g, 22 mmol) and sodium tert-butoxide (3.8 g, 40 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 11 (7.1 g). (Yield 52%, MS: [M+H] + = 681)

Synthesis Example 12

In a nitrogen atmosphere, sub12 (10 g, 16.6 mmol), formula a (4 g, 18.3 mmol) and sodium tert-butoxide (3.2 g, 33.2 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 12 (7.3 g). (Yield 56%, MS: [M+H]+= 783)

Synthesis Example 13

In a nitrogen atmosphere, sub13 (10 g, 17.4 mmol), formula a (4.1 g, 19.1 mmol) and sodium tert-butoxide (3.3 g, 34.7 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 13 (7.4 g). (Yield 56%, MS: [M+H] + = 757)

Synthesis Example 14

In a nitrogen atmosphere, sub14 (10 g, 16.2 mmol), formula a (3.9 g, 17.9 mmol) and sodium tert-butoxide (3.1 g, 32.5 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 14 (6.8 g). (Yield 53%, MS: [M+H] + = 797)

Synthesis Example 15

In a nitrogen atmosphere, sub15 (10 g, 16.5 mmol), formula a (3.9 g, 18.1 mmol) and sodium tert-butoxide (3.2 g, 33 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 15 (7.8 g). (Yield 60%, MS: [M+H] + = 787)

Synthesis Example 16

In a nitrogen atmosphere, sub16 (10 g, 22.2 mmol), formula b (6.5 g, 24.4 mmol) and sodium tert-butoxide (4.3 g, 44.4 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 16 (9.8 g). (Yield 65%, MS: [M+H] + = 681)

Synthesis Example 17

In a nitrogen atmosphere, sub17 (10 g, 18.2 mmol), formula a (4.3 g, 20 mmol) and sodium tert-butoxide (3.5 g, 36.4 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 17 (6.9 g). (Yield 52%, MS: [M+H] + = 731)

Synthesis Example 18

In nitrogen atmosphere, sub18 (10 g, 16.7 mmol), formula b (4.9 g, 18.3 mmol) and sodium tert-butoxide (3.2 g, 33.3 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 18 (8.2 g). (Yield 59%, MS: [M+H]+= 831)

Synthesis Example 19

In a nitrogen atmosphere, sub19 (10 g, 14.8 mmol), formula c (4.3 g, 16.3 mmol) and sodium tert-butoxide (2.8 g, 29.6 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 19 (8 g). (Yield 60%, MS: [M+H] + =907)

Synthesis Example 20

In a nitrogen atmosphere, sub20 (10 g, 16 mmol), formula a (3.8 g, 17.6 mmol) and sodium tert-butoxide (3.1 g, 31.9 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 20 (8.6 g). (Yield 67%, MS: [M+H] + = 807)

Synthesis Example 21

In a nitrogen atmosphere, sub21 (10 g, 16 mmol), formula b (4.7 g, 17.6 mmol) and sodium tert-butoxide (3.1 g, 31.9 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 21 (8.3 g). (Yield 61%, MS: [M+H] + = 857)

Synthesis Example 22

In a nitrogen atmosphere, sub22 (10 g, 15.4 mmol), formula a (3.7 g, 16.9 mmol) and sodium tert-butoxide (3 g, 30.8 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 22 (7 g). (Yield 55%, MS: [M+H]+= 831)

Synthesis Example 23

In a nitrogen atmosphere, sub23 (10 g, 17.4 mmol), formula c (5.1 g, 19.2 mmol) and sodium tert-butoxide (3.3 g, 34.8 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 23 (8.1 g). (Yield 58%, MS: [M+H] + = 805)

Synthesis Example 24

In a nitrogen atmosphere, sub24 (10 g, 15.4 mmol), chemical formula d (4.5 g, 16.9 mmol) and sodium tert-butoxide (3 g, 30.8 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 24 (7.9 g). (Yield 58%, MS: [M+H] + = 881)

Synthesis Example 25

In a nitrogen atmosphere, sub25 (10 g, 18.5 mmol), chemical formula d (5.4 g, 20.4 mmol) and sodium tert-butoxide (3.6 g, 37 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 25 (7.7 g). (Yield 54%, MS: [M+H] + = 771)

Synthesis Example 26

In a nitrogen atmosphere, sub26 (10 g, 15 mmol), formula d (4.4 g, 16.5 mmol) and sodium tert-butoxide (2.9 g, 30 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 26 (7.4 g). (Yield 55%, MS: [M+H] + = 897)

Synthesis Example 27

In a nitrogen atmosphere, sub27 (10 g, 15.6 mmol), formula c (4.6 g, 17.2 mmol) and sodium tert-butoxide (3 g, 31.2 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 27 (7.6 g). (Yield 56%, MS: [M+H] + = 871)

Synthesis Example 28

In a nitrogen atmosphere, sub28 (10 g, 15 mmol), chemical formula d (4.4 g, 16.5 mmol) and sodium tert-butoxide (2.9 g, 30 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 28 (8.7 g). (Yield 65%, MS: [M+H]+= 897)

Synthesis Example 29

In a nitrogen atmosphere, sub29 (10 g, 14.7 mmol), formula c (4.3 g, 16.1 mmol) and sodium tert-butoxide (2.8 g, 29.3 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 29 (9.1 g). (Yield 68%, MS: [M+H]+= 913)

Synthesis Example 30

In a nitrogen atmosphere, sub30 (10 g, 15.6 mmol), formula a (3.7 g, 17.2 mmol) and sodium tert-butoxide (3 g, 31.2 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 30 (8.8 g). (Yield 69%, MS: [M+H] + = 821)

Synthesis Example 31

In a nitrogen atmosphere, sub31 (10 g, 15.6 mmol), formula b (4.6 g, 17.2 mmol) and sodium tert-butoxide (3 g, 31.2 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 31 (8.6 g). (Yield 63%, MS: [M+H] + = 871)

Synthesis Example 32

In a nitrogen atmosphere, sub32 (10 g, 20 mmol), formula a (4.8 g, 22 mmol) and sodium tert-butoxide (3.8 g, 40 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 32 (6.9 g). (Yield 51%, MS: [M+H]+= 681)

Synthesis Example 33

In a nitrogen atmosphere, sub33 (10 g, 17.4 mmol), chemical formula d (5.1 g, 19.1 mmol) and sodium tert-butoxide (3.3 g, 34.7 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 33 (9.5 g). (Yield 68%, MS: [M+H] + = 807)

Synthesis Example 34

In a nitrogen atmosphere, sub34 (10 g, 16.7 mmol), formula a (4 g, 18.3 mmol) and sodium tert-butoxide (3.2 g, 33.3 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 34 (6.6 g). (Yield 51%, MS: [M+H] + = 781)

Synthesis Example 35

In a nitrogen atmosphere, sub35 (10 g, 16 mmol), formula b (4.7 g, 17.6 mmol) and sodium tert-butoxide (3.1 g, 31.9 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 35 (7 g). (Yield 51%, MS: [M+H] + = 857)

Synthesis Example 36

In a nitrogen atmosphere, sub36 (10 g, 15.4 mmol), formula a (3.7 g, 16.9 mmol) and sodium tert-butoxide (3 g, 30.8 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 36 (7.4 g). (Yield 58%, MS: [M+H] + = 831)

Synthesis Example 37

In a nitrogen atmosphere, sub37 (10 g, 14.3 mmol), formula b (4.2 g, 15.7 mmol) and sodium tert-butoxide (2.7 g, 28.6 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 37 (9 g). (Yield 68%, MS: [M+H] + = 931)

Synthesis Example 38

In a nitrogen atmosphere, sub38 (10 g, 15.4 mmol), formula c (4.5 g, 16.9 mmol) and sodium tert-butoxide (3 g, 30.8 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 38 (7 g). (Yield 52%, MS: [M+H] + = 881)

Synthesis Example 39

In a nitrogen atmosphere, sub39 (10 g, 16.9 mmol), chemical formula a (4.1 g, 18.6 mmol) and sodium tert-butoxide (3.3 g, 33.9 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 39 (8.5 g). (Yield 65%, MS: [M+H] + = 771)

Synthesis Example 40

In a nitrogen atmosphere, sub40 (10 g, 16.9 mmol), formula d (5 g, 18.6 mmol) and sodium tert-butoxide (3.3 g, 33.9 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 40 (9.2 g). (Yield 66%, MS: [M+H]+= 821)

Synthesis Example 41

In a nitrogen atmosphere, sub41 (10 g, 16.5 mmol), formula c (4.9 g, 18.1 mmol) and sodium tert-butoxide (3.2 g, 33 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 41 (9.7 g). (Yield 70%, MS: [M+H] + = 837)

Synthesis Example 42

In a nitrogen atmosphere, sub42 (10 g, 14.7 mmol), formula c (4.3 g, 16.1 mmol) and sodium tert-butoxide (2.8 g, 29.3 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 42 (7.1 g). (Yield 53%, MS: [M+H]+= 913)

Synthesis Example 43

In a nitrogen atmosphere, sub43 (10 g, 14.4 mmol), formula d (4.2 g, 15.8 mmol) and sodium tert-butoxide (2.8 g, 28.7 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 43 (7.1 g). (Yield 53%, MS: [M+H] + = 927)

Synthesis Example 44

In a nitrogen atmosphere, sub44 (10 g, 14.7 mmol), formula b (4.3 g, 16.2 mmol) and sodium tert-butoxide (2.8 g, 29.4 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 44 (9.2 g). (Yield 69%, MS: [M+H]+= 911)

Synthesis Example 45

In a nitrogen atmosphere, sub45 (10 g, 19 mmol), formula d (5.6 g, 20.9 mmol) and sodium tert-butoxide (3.7 g, 38 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 45 (7.9 g). (Yield 55%, MS: [M+H] + = 757)

Synthesis Example 46

In a nitrogen atmosphere, sub46 (10 g, 18.2 mmol), chemical formula c (5.3 g, 20 mmol) and sodium tert-butoxide (3.5 g, 36.4 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 46 (8.9 g). (Yield 63%, MS: [M+H] + = 781)

Synthesis Example 47

In a nitrogen atmosphere, sub47 (10 g, 16.7 mmol), formula a (4 g, 18.3 mmol) and sodium tert-butoxide (3.2 g, 33.3 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 47 (6.9 g). (Yield 53%, MS: [M+H]+= 781)

Synthesis Example 48

In a nitrogen atmosphere, sub48 (10 g, 16 mmol), chemical formula d (4.7 g, 17.6 mmol) and sodium tert-butoxide (3.1 g, 31.9 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 48 (8.9 g). (Yield 65%, MS: [M+H] + = 857)

Synthesis Example 49

In a nitrogen atmosphere, sub49 (10 g, 15.3 mmol), formula c (4.5 g, 16.9 mmol) and sodium tert-butoxide (2.9 g, 30.7 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 49 (8.4 g). (Yield 62%, MS: [M+H]+= 883)

Synthesis Example 50

In a nitrogen atmosphere, sub50 (10 g, 16 mmol), chemical formula c (4.7 g, 17.6 mmol) and sodium tert-butoxide (3.1 g, 31.9 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 50 (9 g). (Yield 66%, MS: [M+H] + = 857)

Synthesis Example 51

In a nitrogen atmosphere, sub51 (10 g, 15.3 mmol), chemical formula d (4.5 g, 16.9 mmol) and sodium tert-butoxide (2.9 g, 30.7 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 51 (8.5 g). (Yield 63%, MS: [M+H] + = 883)

Synthesis Example 52

In a nitrogen atmosphere, sub52 (10 g, 15.5 mmol), formula b (4.6 g, 17 mmol) and sodium tert-butoxide (3 g, 31 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 52 (9 g). (Yield 66%, MS: [M+H] + = 876)

Synthesis Example 53

In a nitrogen atmosphere, sub53 (10 g, 15.6 mmol), formula c (4.6 g, 17.2 mmol) and sodium tert-butoxide (3 g, 31.2 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 53 (8.3 g). (Yield 61%, MS: [M+H] + = 871)

Synthesis Example 54

In a nitrogen atmosphere, sub54 (10 g, 15.2 mmol), chemical formula d (4.5 g, 16.8 mmol) and sodium tert-butoxide (2.9 g, 30.5 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 54 (8.6 g). (Yield 64%, MS: [M+H] + = 887)

Synthesis Example 55

In a nitrogen atmosphere, sub55 (10 g, 15.2 mmol), formula b (4.5 g, 16.8 mmol) and sodium tert-butoxide (2.9 g, 30.5 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 55 (8.4 g). (Yield 62%, MS: [M+H] + = 887)

Synthesis Example 56

In a nitrogen atmosphere, sub56 (10 g, 15 mmol), chemical formula a (3.6 g, 16.5 mmol) and sodium tert-butoxide (2.9 g, 30 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 56 (8 g). (Yield 63%, MS: [M+H] + = 847)

Synthesis Example 57

In a nitrogen atmosphere, sub57 (10 g, 14 mmol), formula a (3.4 g, 15.4 mmol) and sodium tert-butoxide (2.7 g, 28.1 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 57 (7.1 g). (Yield 57%, MS: [M+H] + = 893)

Synthesis Example 58

In a nitrogen atmosphere, sub58 (10 g, 14.4 mmol), formula b (4.2 g, 15.8 mmol) and sodium tert-butoxide (2.8 g, 28.7 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 58 (8.1 g). (Yield 61%, MS: [M+H] + = 927)

Synthesis Example 59

In a nitrogen atmosphere, sub59 (10 g, 13.5 mmol), formula b (4 g, 14.8 mmol) and sodium tert-butoxide (2.6 g, 27 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 59 (9.2 g). (Yield 70%, MS: [M+H] + = 972

Comparative Example 1

A glass substrate coated with a thin film coated with ITO (indium tin oxide) at a thickness of 1,000 에 was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as the detergent, and distilled water filtered secondarily as a filter of Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice for 10 minutes 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.

The following HI-1 compound was formed to a thickness of 1150 으로 as a hole injection layer on the prepared ITO transparent electrode, but the following A-1 compound was p-doped at a concentration of 1.5%. The following HT-1 compound was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 800 mm 2. Subsequently, the following EB-1 compound was vacuum-deposited to a thickness of 150 mm 2 on the hole transport layer to form an electron blocking layer. Subsequently, the following RH-1 compound and the following Dp-7 compound were vacuum-deposited at a weight ratio of 98:2 on the EB-1 deposition film to form a 400-nm-thick red light-emitting layer. A hole blocking layer was formed by vacuum-depositing the following HB-1 compound with a thickness of 30 Pa on the light emitting layer. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum deposited on the hole blocking layer in a weight ratio of 2:1 to form an electron injection and transport layer with a thickness of 300 MPa. On the electron injection and transport layer, lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 1,000 순차적 were sequentially deposited to form a negative electrode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 2 × 10 ^{- An} organic light emitting device was manufactured by maintaining ⁷ to 5×10 ⁻⁶ torr.

Examples 1 to 59

An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using the compound shown in Table 1 below instead of RH-1 in the organic light emitting diode of Comparative Example 1.

Comparative Examples 2 to 31

An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using the compound shown in Table 1 below instead of RH-1 in the organic light emitting diode of Comparative Example 1.

When a current was applied to the organic light emitting devices prepared in Examples 1 to 59 and Comparative Examples 1 to 31, voltage, efficiency, and lifetime were measured (based on 6000 nit), and the results are shown in Table 1 below. . Life time T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

division matter Driving voltage (V) Efficiency (cd/A) Life T95(hr) Luminous color Comparative Example 1 RH-1 4.34 38.3 193 Red Example 1 Compound 1 3.63 43.2 241 Red Example 2 Compound 2 3.71 42.9 240 Red Example 3 Compound 3 3.79 43.7 248 Red Example 4 Compound 4 3.78 43.8 243 Red Example 5 Compound 5 3.87 44.0 278 Red Example 6 Compound 6 3.91 45.1 284 Red Example 7 Compound 7 3.92 44.7 299 Red Example 8 Compound 8 3.97 45.9 290 Red Example 9 Compound 9 3.96 45.8 281 Red Example 10 Compound 10 3.92 47.0 297 Red Example 11 Compound 11 3.71 46.7 261 Red Example 12 Compound 12 3.73 47.8 271 Red Example 13 Compound 13 3.75 46.8 278 Red Example 14 Compound 14 3.74 46.9 249 Red Example 15 Compound 15 3.72 46.6 258 Red Example 16 Compound 16 3.51 45.3 288 Red Example 17 Compound 17 3.53 45.7 318 Red Example 18 Compound 18 3.50 45.1 331 Red Example 19 Compound 19 3.57 45.3 310 Red Example 20 Compound 20 3.46 45.2 325 Red Example 21 Compound 21 3.50 45.0 327 Red Example 22 Compound 22 3.47 46.5 315 Red Example 23 Compound 23 3.53 46.0 320 Red Example 24 Compound 24 3.48 46.7 317 Red Example 25 Compound 25 3.49 47.5 313 Red Example 26 Compound 26 3.52 43.4 328 Red Example 27 Compound 27 3.58 47.1 323 Red Example 28 Compound 28 3.54 48.0 331 Red Example 29 Compound 29 3.58 47.3 315 Red Example 30 Compound 30 3.67 50.2 327 Red Example 31 Compound 31 3.68 48.7 332 Red Example 32 Compound 32 3.66 49.1 341 Red Example 33 Compound 33 3.63 48.8 352 Red Example 34 Compound 34 3.51 48.3 337 Red Example 35 Compound 35 3.55 48.9 353 Red Example 36 Compound 36 3.62 48.5 342 Red Example 37 Compound 37 3.67 49.7 362 Red Example 38 Compound 38 3.62 48.3 350 Red Example 39 Compound 39 3.54 48.5 353 Red Example 40 Compound 40 3.61 49.4 347 Red Example 41 Compound 41 3.57 50.6 341 Red Example 42 Compound 42 3.48 48.9 338 Red Example 43 Compound 43 3.39 49.5 343 Red Example 44 Compound 44 3.47 49.1 342 Red Example 45 Compound 45 3.31 48.3 327 Red Example 46 Compound 46 3.34 48.7 293 Red Example 47 Compound 47 3.38 47.3 280 Red Example 48 Compound 48 3.40 47.5 288 Red Example 49 Compound 49 3.48 45.8 311 Red Example 50 Compound 50 3.33 47.5 304 Red Example 51 Compound 51 3.42 48.9 297 Red Example 52 Compound 52 3.40 49.3 323 Red Example 53 Compound 53 3.46 50.1 314 Red Example 54 Compound 54 3.48 49.7 295 Red Example 55 Compound 55 3.41 48.3 307 Red Example 56 Compound 56 3.43 49.1 327 Red Example 57 Compound 57 3.48 48.5 315 Red Example 58 Compound 58 3.40 47.6 353 Red Example 59 Compound 59 3.52 50.2 301 Red Comparative Example 2 C-1 4.13 37.2 131 Red Comparative Example 3 C-2 4.81 34.1 140 Red Comparative Example 4 C-3 4.30 35.1 167 Red Comparative Example 5 C-4 4.68 33.0 79 Red Comparative Example 6 C-5 4.41 32.4 97 Red Comparative Example 7 C-6 4.77 29.7 61 Red Comparative Example 8 C-7 4.21 34.0 103 Red Comparative Example 9 C-8 4.19 35.7 114 Red Comparative Example 10 C-9 4.71 31.3 73 Red Comparative Example 11 C-10 4.19 35.7 114 Red Comparative Example 12 C-11 4.71 31.3 73 Red Comparative Example 13 C-12 4.71 31.3 73 Red Comparative Example 14 C-13 4.46 34.3 108 Red Comparative Example 15 C-14 4.21 35.5 112 Red Comparative Example 16 C-15 3.95 36.1 93 Red Comparative Example 17 C-16 4.51 32.5 91 Red Comparative Example 18 C-17 4.33 36.8 107 Red Comparative Example 19 C-18 4.01 34.7 123 Red Comparative Example 20 C-19 3.91 36.5 152 Red Comparative Example 21 C-20 3.85 39.1 107 Red Comparative Example 22 C-21 4.03 37.5 152 Red Comparative Example 23 C-22 5.41 10.3 31 Red Comparative Example 24 C-23 5.51 8.7 23 Red Comparative Example 25 C-24 4.52 35.4 61 Red Comparative Example 26 C-25 4.19 39.8 197 Red Comparative Example 27 C-26 4.08 40.3 201 Red Comparative Example 28 C-27 4.04 41.8 181 Red Comparative Example 29 C-28 3.87 42.9 226 Red Comparative Example 30 C-29 3.89 37.1 173 Red Comparative Example 31 C-30 3.81 32.6 124 Red

When a current was applied to the organic light-emitting devices fabricated in Examples 1 to 59 and Comparative Examples 1 to 31, the results of Table 1 were obtained. The red organic light-emitting device of Comparative Example 1 used a material that has been widely used in the past, and has a structure using compound [EB-1] as an electron blocking layer and RH-1/Dp-7 as a red light-emitting layer. In Comparative Examples 2 to 31, an organic light-emitting device was manufactured using C-1 to C-30 instead of RH-1.

Looking at the results in Table 1 above, when the compound of the present invention was used as a host of the red light emitting layer, the driving voltage was significantly lowered by nearly 30% compared to the material of the comparative example, and the efficiency was increased by more than 25%. It was found that the energy transfer of In addition, it was found that while maintaining high efficiency, the lifespan characteristics can be improved more than twice. This can be judged to be because the compound of the present invention has higher stability to electrons and holes than the comparative example compound.

Examples 60-159

In the organic light emitting device of Comparative Example 1, instead of RH-1, the first host and the second host described in Table 2 were vacuum co-deposited at a 1:1 weight ratio, except for this, in the same manner as in Comparative Example 1 A light emitting device was manufactured.

division Host 1 Host 2 Driving voltage (V) Efficiency (cd/A) Life T95(hr) Luminous color Example 60 Compound 1 Z-1 3.65 47.2 407 Red Example 61 Compound 1 Z-4 3.68 46.9 401 Red Example 62 Compound 1 Z-10 3.69 47.5 409 Red Example 63 Compound 1 Z-13 3.68 45.8 413 Red Example 64 Compound 1 Z-21 3.65 44.9 418 Red Example 65 Compound 1 Z-25 3.67 46.1 413 Red Example 66 Compound 1 Z-31 3.70 47.3 420 Red Example 67 Compound 1 Z-33 3.68 44.0 418 Red Example 68 Compound 6 Z-1 3.79 46.5 462 Red Example 69 Compound 6 Z-4 3.78 46.8 461 Red Example 70 Compound 6 Z-10 3.82 46.9 448 Red Example 71 Compound 6 Z-13 3.78 45.5 451 Red Example 72 Compound 6 Z-21 3.83 46.7 434 Red Example 73 Compound 6 Z-25 3.80 46.9 441 Red Example 74 Compound 6 Z-31 3.82 46.2 457 Red Example 75 Compound 6 Z-33 3.77 45.8 452 Red Example 76 Compound 11 Z-1 3.58 47.2 453 Red Example 77 Compound 11 Z-4 3.57 47.7 451 Red Example 78 Compound 11 Z-10 3.59 48.0 449 Red Example 79 Compound 11 Z-13 3.55 47.6 467 Red Example 80 Compound 11 Z-21 3.61 47.3 452 Red Example 81 Compound 11 Z-25 3.59 48.7 461 Red Example 82 Compound 11 Z-31 3.60 47.8 468 Red Example 83 Compound 11 Z-33 3.58 48.5 455 Red Example 84 Compound 17 Z-2 3.59 47.2 417 Red Example 85 Compound 17 Z-7 3.58 46.9 398 Red Example 86 Compound 17 Z-11 3.50 47.9 414 Red Example 87 Compound 17 Z-15 3.58 48.7 413 Red Example 88 Compound 17 Z-18 3.57 48.5 395 Red Example 89 Compound 17 Z-19 3.61 47.3 411 Red Example 90 Compound 17 Z-22 3.59 47.7 495 Red Example 91 Compound 17 Z-23 3.50 46.9 397 Red Example 92 Compound 17 Z-27 3.52 47.1 410 Red Example 93 Compound 17 Z-34 3.58 47.8 496 Red Example 94 Compound 23 Z-2 3.49 46.9 431 Red Example 95 Compound 23 Z-7 3.48 46.3 452 Red Example 96 Compound 23 Z-11 3.49 46.8 442 Red Example 97 Compound 23 Z-15 3.51 46.5 464 Red Example 98 Compound 23 Z-18 3.45 46.2 451 Red Example 99 Compound 23 Z-19 3.48 46.7 459 Red Example 100 Compound 23 Z-22 3.52 46.9 463 Red Example 101 Compound 23 Z-23 3.50 47.4 464 Red Example 102 Compound 23 Z-27 3.47 46.5 460 Red Example 103 Compound 23 Z-34 3.49 47.0 457 Red Example 104 Compound 27 Z-2 3.49 51.0 462 Red Example 105 Compound 27 Z-7 3.47 50.3 481 Red Example 106 Compound 27 Z-11 3.52 51.4 473 Red Example 107 Compound 27 Z-15 3.49 51.9 462 Red Example 108 Compound 27 Z-18 3.47 51.5 468 Red Example 109 Compound 27 Z-19 3.46 52.7 477 Red Example 110 Compound 27 Z-22 3.50 51.5 486 Red Example 111 Compound 27 Z-23 3.48 52.3 471 Red Example 112 Compound 27 Z-27 3.51 51.7 469 Red Example 113 Compound 27 Z-34 3.53 52.5 473 Red Example 114 Compound 29 Z-2 3.48 51.5 461 Red Example 115 Compound 29 Z-7 3.45 50.6 457 Red Example 116 Compound 29 Z-11 3.40 52.7 449 Red Example 117 Compound 29 Z-15 3.49 52.1 468 Red Example 118 Compound 29 Z-18 3.51 52.7 471 Red Example 119 Compound 29 Z-19 3.43 53.4 466 Red Example 120 Compound 29 Z-22 3.47 52.6 481 Red Example 121 Compound 29 Z-23 3.44 52.9 458 Red Example 122 Compound 29 Z-27 3.49 53.1 467 Red Example 123 Compound 29 Z-34 3.50 52.4 463 Red Example 124 Compound 34 Z-3 3.41 50.3 461 Red Example 125 Compound 34 Z-8 3.43 50.1 475 Red Example 126 Compound 34 Z-12 3.41 52.7 454 Red Example 127 Compound 34 Z-16 3.40 50.5 460 Red Example 128 Compound 34 Z-20 3.47 51.8 447 Red Example 129 Compound 34 Z-29 3.44 50.6 476 Red Example 130 Compound 34 Z-30 3.41 49.0 440 Red Example 131 Compound 34 Z-32 3.45 51.6 479 Red Example 132 Compound 41 Z-3 3.42 50.0 481 Red Example 133 Compound 41 Z-8 3.39 50.7 498 Red Example 134 Compound 41 Z-12 3.38 51.2 470 Red Example 135 Compound 41 Z-16 3.44 50.4 467 Red Example 136 Compound 41 Z-20 3.39 51.9 465 Red Example 137 Compound 41 Z-29 3.38 51.3 443 Red Example 138 Compound 41 Z-30 3.40 50.9 465 Red Example 139 Compound 41 Z-32 3.38 51.3 473 Red Example 140 Compound 50 Z-5 3.39 50.6 431 Red Example 141 Compound 50 Z-6 3.38 50.7 438 Red Example 142 Compound 50 Z-9 3.39 50.1 405 Red Example 143 Compound 50 Z-14 3.36 51.5 418 Red Example 144 Compound 50 Z-17 3.31 51.6 438 Red Example 145 Compound 50 Z-24 3.39 49.3 429 Red Example 146 Compound 50 Z-26 3.37 50.2 437 Red Example 147 Compound 50 Z-28 3.32 51.8 458 Red Example 148 Compound 50 Z-35 3.40 52.9 451 Red Example 149 Compound 50 Z-36 3.38 50.7 455 Red Example 150 Compound 57 Z-5 3.39 52.5 399 Red Example 151 Compound 57 Z-6 3.41 51.3 401 Red Example 152 Compound 57 Z-9 3.39 52.8 388 Red Example 153 Compound 57 Z-14 3.43 51.7 379 Red Example 154 Compound 57 Z-17 3.35 51.0 412 Red Example 155 Compound 57 Z-24 3.39 51.8 388 Red Example 156 Compound 57 Z-26 3.39 50.7 403 Red Example 157 Compound 57 Z-28 3.43 51.5 389 Red Example 158 Compound 57 Z-35 3.40 51.3 393 Red Example 159 Compound 57 Z-36 3.36 50.8 387 Red

The results in Table 2 showed the result of co-deposition of two types of hosts. When the first host and the second host were used in a 1:1 weight ratio, the results were better than the results of using only the first host. As the amount of holes increases as the second host is used, it can be seen that electrons and holes in the red light-emitting layer maintain a more stable balance, and efficiency and lifespan increase significantly. In conclusion, it can be seen that when the compound of the present invention is used as a host for a red light emitting layer, it is possible to improve driving voltage, light emitting efficiency, and life characteristics of an organic light emitting device.

1: Substrate
2: first electrode
3: light emitting layer
4: second electrode
5: hole injection layer
6: hole transport layer
7: e-low layer
8: hole block
9: electron injection and transport layer

Claims (14)

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

In Chemical Formula 1,
R1 to R4 are each independently hydrogen; Or deuterium,
R5 and R6 are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a is an integer from 0 to 6,
b and d are each independently an integer of 0 to 4,
c is an integer from 0 to 2,
a to d are each independently, when two or more, the substituents in parentheses are the same as or different from each other,
b to d are each independently, and when two or more, two or more R2 to R4 may each independently combine with an adjacent substituent to form a ring. The compound of claim 1, wherein the compound represented by Formula 1 is selected from any one of the following Formulas 2 to 4:
[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4, R1 to R6 and a to d are as defined in Formula 1. The compound of claim 1, wherein the compound represented by Formula 1 is selected from any one of the following Formulas 2-1 to 2-8:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

[Formula 2-8]

In Formulas 2-1 to 2-8, R4 to R6 and d are as defined in Formula 1,
R8 is hydrogen; Or deuterium,
f is an integer from 0 to 8,
When f is 2 or more, a plurality of R8s are the same as or different from each other. The compound of claim 1, wherein the compound represented by Formula 1 is selected from any one of the following Formulas 3-1 to 3-8:
[Chemical Formula 3-1]

[Formula 3-2]

[Chemical Formula 3-3]

[Formula 3-4]

[Chemical Formula 3-5]

[Formula 3-6]

[Formula 3-7]

[Chemical Formula 3-8]

In Formulas 3-1 to 3-8, R4 to R6 and d are as defined in Formula 1,
R8 is hydrogen; Or deuterium,
f is an integer from 0 to 8,
When f is 2 or more, a plurality of R8s are the same as or different from each other. The compound of claim 1, wherein the compound represented by Formula 1 is selected from any one of the following Formulas 4-1 to 4-8:
[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

[Formula 4-4]

[Formula 4-5]

[Formula 4-6]

[Formula 4-7]

[Formula 4-8]

In Formulas 4-1 to 4-8, R4 to R6 and d are as defined in Formula 1,
R7 is hydrogen; Or deuterium,
e1 and e2 are each 0 or 1, and the sum of e1 and e2 is 1 to 2,
e is an integer from 0 to 10,
When e is 2 or more, a plurality of R7s are the same as or different from each other. The method according to claim 1,
The compound represented by Formula 1 is a compound selected from the following compounds:

. A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode,
At least one of the organic material layers comprises the compound according to any one of claims 1 to 6. 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 of Formula 1. 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 of Formula 1 as a host. The method according to claim 7,
The organic material layer includes a hole injection layer or a hole transport layer,
The hole injection layer or the hole transport layer is an organic light emitting device containing the compound of Formula 1. The method according to claim 7,
The organic material layer includes an electron transport layer or an electron injection layer,
The electron transport layer or the electron injection layer is an organic light-emitting device comprising the compound of Formula 1. The method according to claim 7,
The organic light-emitting device further comprises one layer or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer. The method according to claim 7,
The organic material layer includes a light emitting layer,
The emission layer includes the compound of Formula 1 as a first host, and further includes a second host represented by the following Formula H:
[Formula H]

In Formula H,
A is a substituted or unsubstituted naphthalene ring,
Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms,
L1 to L3 are each independently a single bond; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms,
Ar2 and Ar3 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms including one or more heteroatoms among N, O and S,
p is an integer from 0 to 9. The method according to claim 13,
The second host represented by Formula H is an organic light emitting device represented by any one of the following structures:

.

.

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