KR102209928B1 - Compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Compound and organic light-emitting device comprising the same TECHNICAL FIELD

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0079367 filed with the Korean Intellectual Property Office on July 9, 2018, the entire contents of which are incorporated herein.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light-emitting device having such a structure, electrons and holes injected from the two electrodes are combined in the organic thin film to form a pair and then emit light while disappearing. The organic thin film may be composed of a single layer or multiple layers as necessary.

The material of the organic thin film may have a light emitting function if necessary. For example, as the organic thin film material, a compound capable of constituting a light emitting layer by itself may be used, or a compound capable of serving as a host or a dopant of the host-dopant-based light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing a role of hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection may be used.

In order to improve the performance, life, or efficiency of an organic light emitting device, the development of a material for an organic thin film is continuously required.

International Patent Application Publication No. 2003-012890

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

An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

Any one of R1 to R4 is directly bonded to any one of R5 to R8 of the following formula (2),

R10 is hydrogen or a substituted or unsubstituted aryl group, m is an integer of 0 to 4, and when m is 2 or more, R10 is the same as or different from each other,

[Formula 2]

In Formulas 1 and 2,

When R3 and R7 are bonded, Ar1 and Ar2 are the same as each other, and are represented by the following formula (3),

When any one of R1 to R4 and any one of R5, R6, and R8 are bonded, or when any one of R7 and R1, R2 and R4 is bonded, at least one of Ar1 and Ar2 is represented by the following formula (3),

Ar1 or Ar2 other than Formula 3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

The substituent that does not bond among R1 to R8 is hydrogen,

R11 is hydrogen or a substituted or unsubstituted aryl group, n is an integer of 0 to 4, and when n is 2 or more, R11 is the same as or different from each other,

[Formula 3]

In Formula 3, X is O or S,

R12 is hydrogen or a substituted or unsubstituted aryl group, o is an integer of 0 to 4, and when o is 2 or more, R12 is the same as or different from each other,

는 화학식 1 또는 2와 결합하는 위치를 의미한다.remind

Means a position bonded to Formula 1 or 2.

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, wherein at least one of the organic material layers includes the above-described compound.

The compound according to an exemplary embodiment of the present application is used in an organic light-emitting device, thereby increasing the luminance of the organic light-emitting device, increasing the lifespan, lowering the driving voltage, improving light efficiency, and improving the lifespan characteristics of the device by thermal stability of the compound. Can be improved.

In the compound represented by Chemical Formula 1 according to the present specification, benzothiazole or benzoxazole is bonded to N having a biscarbazole structure, thereby increasing stability against electrons.

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

The 3,3'-biscarbazole structure of the compound represented by Formula 1 according to the present specification has excellent stability against holes, and in this case, the same benzothiazole or benzoxazole is combined with N to obtain Formula 1 The displayed compound has a symmetrical structure, which also improves stability against electrons.

In addition, bonds other than 3,3'-biscarbazole such as 1,1'-biscarbazole, 1,2'-biscarbazole, 1,3'-biscarbazole, 2,3'-biscarbazole, etc. When it has a position, there is an effect of low voltage and long life by combining benzoxazole or benzothiazole.

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

The term "substituted" 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 as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Alkyl group; Cycloalkyl group; Alkoxy group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any 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-ethylpropyl, 1,1-dimethylpropyl, 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 30 carbon atoms, and 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, etc., but are limited thereto. It is not.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. May be, but is 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 it is preferably 6 to 30 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 preferably 10 to 24 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a pyrenyl group, a perylenyl group, a chrysene group, a fluorene group, and the like, but is not limited thereto.

In the present specification, the heteroaryl group is an atom other than carbon and contains one or more heteroatoms, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, Si, and S. have. The number of carbon atoms of the heteroaryl group is not particularly limited, but is preferably 2 to 60 carbon atoms or 2 to 30 carbon atoms. Examples of the heteroaryl group include thiophene group, furan group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, tria Genyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group , Isoquinolinyl group, indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophene group, dibenzothiophene group , Benzofuran group, dibenzofuran group, benzosilol group, dibenzosilol group, phenanthrolinyl group, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, phenoxazine group, and condensation structures thereof, etc. However, it is not limited to these.

In the exemplary embodiment of the present specification, R10 is hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R10 is hydrogen or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R10 is hydrogen or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In the exemplary embodiment of the present specification, R10 is hydrogen or an aryl group having 6 to 12 carbon atoms.

In the exemplary embodiment of the present specification, R10 is hydrogen, a phenyl group, a biphenyl group, or a naphthyl group.

In the exemplary embodiment of the present specification, m is 0.

In the exemplary embodiment of the present specification, m is 1.

In the exemplary embodiment of the present specification, m is 4.

In the exemplary embodiment of the present specification, R11 is hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R11 is hydrogen or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R11 is hydrogen or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In the exemplary embodiment of the present specification, R11 is hydrogen or an aryl group having 6 to 12 carbon atoms.

In the exemplary embodiment of the present specification, R11 is hydrogen, a phenyl group, a biphenyl group, or a naphthyl group.

In the exemplary embodiment of the present specification, n is 0.

In the exemplary embodiment of the present specification, n is 1.

In the exemplary embodiment of the present specification, n is 4.

In the exemplary embodiment of the present specification, R12 is hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R12 is hydrogen or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R12 is hydrogen or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In the exemplary embodiment of the present specification, R12 is hydrogen or an aryl group having 6 to 12 carbon atoms.

In the exemplary embodiment of the present specification, R12 is hydrogen, a phenyl group, a biphenyl group, or a naphthyl group.

In the exemplary embodiment of the present specification, o is 0.

In the exemplary embodiment of the present specification, o is 1.

In the exemplary embodiment of the present specification, o is 4.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is represented by the following Formula 1-1.

[Formula 1-1]

For Formula 1-1,

At least one of Ar1 and Ar2 is represented by Formula 3,

Ar1 or Ar2 other than Formula 3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is represented by the following Formula 1-2.

[Formula 1-2]

In Formula 1-2,

At least one of Ar1 and Ar2 is represented by Formula 3,

Ar1 or Ar2 other than Formula 3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, when represented by Formula 1-2 is 1,1'-biscarbazole, 1,2'-biscarbazole, 1,3'-biscarbazole, 1,4' -Can be biscarbazole, which means binding to No. 1 of biscarbazole. When the compound in this case is used in an organic light-emitting device, there is an effect of low voltage.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is represented by any one of the following Formulas 1-3 to 1-5.

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Formulas 1-3 to 1-5, the definitions of Ar1 and Ar2 are the same as in Formula 1.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is represented by any one of the following Formulas 1-6 to 1-8.

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Formulas 1-6 to 1-8, the definitions of Ar1 and Ar2 are the same as in Formula 1.

In the exemplary embodiment of the present specification, Ar1 or Ar2 other than Formula 3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 or Ar2 other than Formula 3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 or Ar2 other than Formula 3 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted triazine group; A substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted pyridine group.

In the exemplary embodiment of the present specification, Ar1 or Ar2 other than Formula 3 is a phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; A naphthyl group unsubstituted or substituted with an aryl group; Terphenyl group unsubstituted or substituted with an aryl group; A phenanthrene group unsubstituted or substituted with an aryl group; Triphenylene group unsubstituted or substituted with an aryl group; A dibenzofuran group unsubstituted or substituted with an aryl group; A dibenzothiophene group unsubstituted or substituted with an aryl group; A benzothiazole group unsubstituted or substituted with an aryl group; A benzoxazole group unsubstituted or substituted with an aryl group; A triazine group unsubstituted or substituted with an aryl group; A pyrimidine group unsubstituted or substituted with an aryl group; Or a pyridine group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, Ar1 or Ar2 other than Formula 3 is a phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; A naphthyl group unsubstituted or substituted with an aryl group; Terphenyl group unsubstituted or substituted with an aryl group; Phenanthren group; Triphenylene group; Dibenzofuran group; Dibenzothiophene group; Benzothiazole group; Benzoxazole group; A triazine group unsubstituted or substituted with an aryl group; A pyrimidine group unsubstituted or substituted with an aryl group; Or a pyridine group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, Ar1 or Ar2 other than Formula 3 is a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a triphenylene group; A biphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a triphenylene group; A naphthyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a triphenylene group; A terphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a triphenylene group; Phenanthren group; Triphenylene group; Dibenzofuran group; Dibenzothiophene group; Benzothiazole group; Benzoxazole group; A triazine group unsubstituted or substituted with a phenyl group, a naphthyl group, or a triphenylene group; A pyrimidine group unsubstituted or substituted with a phenyl group, a naphthyl group, or a triphenylene group; Or a phenyl group, a naphthyl group, or a pyridine group unsubstituted or substituted with a triphenylene group.

In an exemplary embodiment of the present specification, the compound of Formula 1 is selected from the following structural formulas.

In an exemplary embodiment of the present specification, the compound of Formula 1 is selected from the following structural formulas.

The compound according to an exemplary embodiment of the present application may be prepared by a manufacturing method described below.

For example, the compound of Formula 1 may have a core structure as shown in Scheme 1 below. Substituents may be combined by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

[Scheme 1]

In Reaction Scheme 1, Ar1 and Ar2 are the same as defined in Chemical Formula 1, and X is a halogen group.

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

In the exemplary embodiment of the present application, 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, wherein at least one of the organic material layers includes the compound.

When a member is referred to herein as being “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 other components may be further included rather than excluding other components unless otherwise stated.

The organic material layer of the organic light emitting device of the present application may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic light emitting device of the present invention, the organic light emitting device 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, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In the exemplary embodiment of the present application, the organic material layer includes an emission layer, and the emission layer includes the compound.

In the exemplary embodiment of the present application, the organic material layer includes an emission layer, and the emission layer includes the compound as a host.

In the exemplary embodiment of the present application, the emission layer includes the compound of Formula 1 as a first host, and further includes a second host.

In the exemplary embodiment of the present application, the emission layer includes a first host and a second host in a weight ratio of 2:1 to 1:2.

In the exemplary embodiment of the present application, the emission layer includes a first host and a second host in a weight ratio of 1: 1.

In the exemplary embodiment of the present application, the second host is a carbazole-based compound.

In the exemplary embodiment of the present application, the second host is a biscarbazole-based compound.

In the exemplary embodiment of the present application, the second host may be represented by Formula A below.

[Formula A]

In Formula A, Ar10 and Ar11 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, Ar10 and Ar11 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted pymiridine group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In the exemplary embodiment of the present specification, Ar10 and Ar11 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; A triazine group unsubstituted or substituted with an aryl group; A pymiridine group unsubstituted or substituted with an aryl group; Or a pyridine group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, Ar10 and Ar11 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; Or a triazine group substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group.

In an exemplary embodiment of the present specification, the compound represented by Formula A may be represented by the following structural formula.

In the exemplary embodiment of the present application, the emission layer further includes a dopant compound.

In the exemplary embodiment of the present application, the emission layer includes the compound of Formula 1 and a dopant.

In the exemplary embodiment of the present application, the emission layer includes a compound of Formula 1 and a dopant, and includes a compound of Formula 1 and a dopant in a content ratio of 100:1 to 1:1.

In the exemplary embodiment of the present application, the emission layer includes a compound of Formula 1 and a dopant, and includes a compound of Formula 1 and a dopant in a content ratio of 100:1 to 2:1.

In the exemplary embodiment of the present application, the emission layer includes the compound of Formula 1 and the dopant, and the compound of Formula 1 and the dopant in a content ratio of 100:1 to 5:1.

In the exemplary embodiment of the present application, the dopant is a metal complex.

In the exemplary embodiment of the present application, the dopant is an iridium-based metal complex.

In the exemplary embodiment of the present application, the organic material layer includes an emission layer, the emission layer includes a dopant, and the dopant material is selected from the following structural formulas.

Dp-1 Dp-2 Dp-3

Dp-4 Dp-5 Dp-6

Dp-7 Dp-8 Dp-9

Dp-10 Dp-11 Dp-12

DP-13 Dp-14 Dp-15

DP-13 Dp-14 Dp-15

Dp-16 Dp-17 Dp-18

Dp-19 Dp-20 Dp-21

Dp-22 Dp-23 Dp-24

Dp-25 Dp-26 Dp-27

Dp-28 Dp-29 Dp-30

Dp-31 Dp-32 Dp-33

Dp-34 Dp-35

In the exemplary embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer.

In the exemplary embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.

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

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

In the exemplary embodiment of the present application, the organic material layer includes an electron blocking layer.

In the exemplary embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer.

In the exemplary embodiment of the present application, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer.

In the exemplary embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.

In the exemplary embodiment of the present application, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.

In the exemplary 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 emission layer and the first electrode, or between the emission layer and the second electrode, and at least one of the organic material layers of the two or more layers includes the compound.

In another exemplary embodiment, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In another embodiment, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

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

1 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, an emission layer 3, and a cathode 4 are sequentially stacked.

2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), an electron transport layer (8), an electron injection layer (9). And the structure of the organic light emitting device in which the cathode 4 is sequentially stacked is illustrated.

In the structure of the organic light-emitting device as described above, the compound may be included in the light-emitting layer 3.

The organic light-emitting device of the present application 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 application, 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.

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

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

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

In the exemplary embodiment of the present application, 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 anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO:Al or SnO ₂ :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.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that injects holes from the electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and is generated from the light emitting layer. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, etc., but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer, and the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

The light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include compounds, dibenzofuran derivatives, and ladder furan compounds. , Pyrimidine derivatives, and the like, but are not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. As an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer. This is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron 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 layer or a 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 the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or light emitting material, and injects holes of excitons generated from the light emitting layer A compound that prevents migration to the layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

The hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., 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.

Preparation of the compound represented by Formula 1 and an organic light emitting device including the same will be described in detail in the following examples. However, the following examples are for illustrative purposes only, and the scope of the present specification is not limited thereto.

< Manufacturing example >

Manufacturing example 1: Preparation of compound A1

1) Preparation of compound A1-1

1-Bromo-9H-carbazole (30 g, 121.90 mmol), 2-chlorobenzene[d] thiazole (22.7 g, 134.09 mmol) and potassium phosphate (51.80 g, 243.79 mmol) in dimethylacetate After adding to amide (dimethylacetamide) (300 mL), it was refluxed. After refluxing for 12 hours, when the reaction is complete, it is cooled to room temperature. After filtration, the mixture was washed with water and ethanol and dried to obtain compound A1-1. (35.6 g, yield 77%; MS:[M+H] ⁺ =380)

2) Preparation of compound A1

Compound A1-1 (30 g, 79.10 mmol) is dissolved in 1,4-dioxane (300 ml). After adding bis(pinacolato)diboron (17.16 g, 102.83 mmol), potassium acetate (23.3 g, 237.29 mmol) and Pd(dppf)Cl ₂ (1.7 g, 2.37 mmol) at 120°C Stir for 6 hours. After the reaction is completed, it is cooled to room temperature and filtered. The filtered solution is distilled to remove the solvent. After extraction with chloroform and water, the organic layer was dried over MgSO ₄ , concentrated, and recrystallized with ethyl acetate to obtain compound A1. (30.0 g, yield 89%; MS:[M+H] ⁺ =427)

Manufacturing example 2: Preparation of compound A2

1) Preparation of compound A2-1

Compound A2-1 was prepared in the same manner as in the method of preparing compound A1-1, except that 2-bromo-9H-carbazole was used instead of compound 1-bromo-9H-carbazole. (42.1 g, yield 91%; MS:[M+H] ⁺ =380)

2) Preparation of compound A2

Compound A2 was prepared in the same manner as the method of preparing compound A1, except that A2-1 was used instead of compound A1-1. (28.3 g, yield 84%; MS:[M+H] ⁺ =427)

Manufacturing example 3: Preparation of compound A3

1) Preparation of compound A3-1

Compound A3-1 was prepared in the same manner as in the method of preparing compound A1-1, except that 3-bromo-9H-carbazole was used instead of compound 1-bromo-9H-carbazole. (42.1 g, yield 91%; MS:[M+H] ⁺ =380)

2) Preparation of compound A3

Compound A3 was prepared in the same manner as the method of preparing compound A1, except that A3-1 was used instead of compound A1-1. (30.0 g, yield 89%; MS:[M+H] ⁺ =427)

Manufacturing example 4: Preparation of compound A4

1) Preparation of compound A4-1

Compound A4-1 was prepared in the same manner as the method for preparing compound A1-1, except that 4-bromo-9H-carbazole was used instead of compound 1-bromo-9H-carbazole. (37.9 g, yield 82%; MS:[M+H] ⁺ =380)

2) Preparation of compound A4

Compound A4 was prepared in the same manner as the method of preparing compound A1, except that A4-1 was used instead of compound A1-1. (31.7 g, yield 94%; MS:[M+H] ⁺ =427)

Manufacturing example 5: Preparation of compound A5

1) Preparation of compound A5-1

Compound A5-1 was prepared in the same manner as in the method of preparing compound A1-1, except that 2-chlorobenzo[d]oxazole was used instead of compound 2-chlorobenzo[d]thiazole. (36.3 g, yield 82%; MS:[M+H] ⁺ =364)

2) Preparation of compound A5

Compound A5 was prepared in the same manner as for preparing compound A1, except that A5-1 was used instead of compound A1-1. (29.2 g, yield 90%; MS:[M+H] ⁺ =411)

Manufacturing example 6: Preparation of compound A6

1) Preparation of compound A6-1

Compound A1-1 was used except that 2-bromo-9H-carbazole and 2-chlorobenzo[d]oxazole were used instead of the compounds 1-bromo-9H-carbazole and 2-chlorobenzo[d]thiazole. Compound A6-1 was prepared in the same manner as in the preparation method. (38.5 g, yield 87%; MS:[M+H] ⁺ =364)

2) Preparation of compound A6

Compound A6 was prepared by the same method as the method of preparing compound A1, except that A6-1 was used instead of compound A1-1. (27.3 g, yield 84%; MS:[M+H] ⁺ =411)

Manufacturing example 7: Preparation of compound A7

1) Preparation of compound A7-1

Compound A1-1 was used, except that 3-bromo-9H-carbazole and 2-chlorobenzo[d]oxazole were used instead of the compounds 1-bromo-9H-carbazole and 2-chlorobenzo[d]thiazole. Compound A7-1 was prepared in the same manner as in the preparation method. (35.9 g, yield 81%; MS:[M+H] ⁺ =364)

2) Preparation of compound A7

Compound A7 was prepared in the same manner as the method for preparing compound A1, except that A7-1 was used instead of compound A1-1. (25.6 g, 79% yield; MS:[M+H] ⁺ =411)

Manufacturing example 8: Preparation of compound A8

1) Preparation of compound A8-1

Compound A1-1 was used, except that 4-bromo-9H-carbazole and 2-chlorobenzo[d]oxazole were used instead of the compounds 1-bromo-9H-carbazole and 2-chlorobenzo[d]thiazole. Compound A8-1 was prepared in the same manner as in the preparation method. (38.5 g, yield 87%; MS:[M+H] ⁺ =364)

2) Preparation of compound A8

Compound A8 was prepared in the same manner as the method for preparing compound A1, except that A8-1 was used instead of compound A1-1. (30.2 g, yield 93%; MS:[M+H] ⁺ =411)

Manufacturing example 9: Preparation of compound B1

Compound B1 was prepared in the same manner as in the method of preparing compound A1-1, except that 2-fluoronaphthalene was used instead of compound 2-chlorobenzo[d]thiazole. (39.5 g, yield 87%; MS:[M+H] ⁺ =372)

Manufacturing example 10: Preparation of compound B2

A method for preparing compound A1-1 except for using 2-bromo-9H-carbazole and 1-fluoronaphthalene instead of compound 1-bromo-9H-carbazole and 2-chlorobenzo[d]thiazole, and Compound B2 was prepared in the same manner. (41.7 g, yield 92%; MS:[M+H] ⁺ =372)

Manufacturing example 11: Preparation of compound B3

Compound A1-1 was prepared except that the compound 3-bromo-9H-carbazole and 2-fluorotriphenylene were used instead of the compound 1-bromo-9H-carbazole and 2-chlorobenzo[d]thiazole Compound B3 was prepared in the same manner as in the method. (46.6 g, yield 81%; MS:[M+H] ⁺ =472)

Manufacturing example 12: Preparation of compound B4

Compound A1-1 was prepared except for using compound 4-bromo-9H-carbazole and 9-fluorophenanthrene instead of compound 1-bromo-9H-carbazole and 2-chlorobenzo[d]thiazole Compound B4 was prepared in the same manner as in the method. (38.6 g, yield 75%; MS:[M+H] ⁺ =422)

Manufacturing example 13: Preparation of compound B5

Compound A1 except that the compound 3-bromo-9H-carbazole and 1-bromodibenzo[b,d]furan were used instead of the compound 1-bromo-9H-carbazole and 2-chlorobenzo[d]thiazole Compound B5 was prepared in the same manner as for preparing -1. (41.2 g, yield 82%; MS:[M+H] ⁺ =412)

Manufacturing example 14: Preparation of compound B6

Compound A1, except that compounds 2-bromo-9H-carbazole and 3-bromodibenzo[b,d]furan were used instead of compounds 1-bromo-9H-carbazole and 2-chlorobenzo[d]thiazole Compound B6 was prepared in the same manner as for preparing -1. (45.7 g, yield 91%; MS:[M+H] ⁺ =412)

Manufacturing example 15: Preparation of compound B7

Compounds except that the compounds 3-bromo-9H-carbazole and 4-bromodibenzo[b,d]thiophene were used instead of the compounds 1-bromo-9H-carbazole and 2-chlorobenzo[d]thiazole Compound B7 was prepared in the same manner as in the method of preparing A1-1. (45.4 g, yield 87%; MS:[M+H] ⁺ =428)

Manufacturing example 16: Preparation of compound B8

Compounds except that the compounds 2-bromo-9H-carbazole and 2-bromodibenzo[b,d]thiophene were used instead of the compounds 1-bromo-9H-carbazole and 2-chlorobenzo[d]thiazole Compound B8 was prepared in the same manner as for preparing A1-1. (40.7 g, yield 78%; MS:[M+H] ⁺ =428)

Manufacturing example 17: Preparation of compound B9

Compound 3-bromo-9H-carbazole and 2-chloro-4,6-diphenyl-1,3,5-tri instead of compound 1-bromo-9H-carbazole and 2-chlorobenzo[d]thiazole Compound B9 was prepared in the same manner as in the method of preparing compound A1-1, except that azine was used. (37.8 g, yield 65%; MS:[M+H] ⁺ =477)

< Example >

Example 1: Preparation of compound 1

After dissolving compound A3 (30 g, 70.37 mmol) and 2-bromo-9-phenyl-9H-carbazole (22.67 g, 70.37 mmol) in tetrahydrofuran (THF) (300 mL), potassium carbonate (Potassium carbonate) (29.2 g, 211.10 mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (2.4 g, 2.11 mmol) was added, followed by heating and stirring for 7 hours. The temperature was lowered to room temperature, and the water layer was separated and removed. After drying over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, recrystallized using ethyl acetate, filtered and dried to prepare compound 1 (26.7 g, yield 70%, MS:[M+H] ⁺ = 542).

Example 2: Preparation of compound 2

Compound A5 and 9-([1,1'-biphenyl]-3-yl)-3-bromo-9H-carbazole was used instead of compound A3 and 2-bromo-9-phenyl-9H-carbazole Except for, compound 2 was prepared in the same manner as for preparing compound 1. (28.6 g, yield 65%; MS:[M+H] ⁺ =602)

Example 3: Preparation of compound 3

Compound A4 and 9-([1,1':3',1''-terphenyl]-5'-yl)-3-bromo instead of compound A3 and 2-bromo-9-phenyl-9H-carbazole Compound 3 was prepared in the same manner as for preparing compound 1, except that -9H-carbazole was used. (36.1 g, yield 74%; MS:[M+H] ⁺ =694)

Example 4: Preparation of compound 4

Compound A1 and 9-([1,1'-biphenyl]-2-yl)-3-bromo-9H-carbazole was used instead of Compound A3 and 2-bromo-9-phenyl-9H-carbazole Except for, compound 4 was prepared in the same manner as for preparing compound 1. (30.9 g, yield 71%; MS:[M+H] ⁺ =618)

Example 5: Preparation of compound 5

Compound 5 was prepared in the same manner as for preparing compound 1, except that compounds A2 and B1 were used instead of compounds A3 and 2-bromo-9-phenyl-9H-carbazole. (25.8 g, yield 62%; MS:[M+H] ⁺ =592)

Example 6: Preparation of compound 6

Compound 6 was prepared in the same manner as for preparing compound 1, except that compounds A7 and B2 were used instead of compounds A3 and 2-bromo-9-phenyl-9H-carbazole. (25.7 g, 61% yield; MS:[M+H] ⁺ =577)

Example 7: Preparation of compound 7

Compound 7 was prepared in the same manner as the method of preparing compound 1, except that compounds A4 and B3 were used instead of compounds A3 and 2-bromo-9-phenyl-9H-carbazole. (34.6 g, yield 71%; MS:[M+H] ⁺ =692)

Example 8: Preparation of compound 8

Compound 8 was prepared in the same manner as in the method of preparing compound 1, except that compounds A and B4 were used instead of compounds A3 and 2-bromo-9-phenyl-9H-carbazole.

(30.7 g, yield 67%; MS:[M+H]+=626)

Example 9: Preparation of compound 9

Compound 9 was prepared in the same manner as the method of preparing compound 1, except that compounds A8 and B5 were used instead of compounds A3 and 2-bromo-9-phenyl-9H-carbazole. (27.9 g, yield 62%; MS:[M+H] ⁺ =616)

Example 10: Preparation of compound 10

Compound 10 was prepared in the same manner as in the method of preparing compound 1, except that B6 was used instead of compound 2-bromo-9-phenyl-9H-carbazole. (32.4 g, yield 73%; MS:[M+H] ⁺ =632)

Example 11: Of compound 11 Produce

Compound 11 was prepared in the same manner as the method of preparing compound 1, except that compounds A2 and B7 were used instead of compounds A3 and 2-bromo-9-phenyl-9H-carbazole. (36.9 g, yield 81%; MS:[M+H] ⁺ =648)

Example 12: Of compound 12 Produce

Compound 12 was prepared in the same manner as the method of preparing compound 1, except that compounds A7 and B8 were used instead of compound A3 and 2-bromo-9-phenyl-9H-carbazole. (31.0 g, yield 67%; MS:[M+H] ⁺ =632)

Example 13: Of compound 13 Produce

Compound 13 was prepared in the same manner as for preparing compound 1, except that compounds A1 and B9 were used instead of compounds A3 and 2-bromo-9-phenyl-9H-carbazole. (27.0 g, yield 55%; MS:[M+H] ⁺ =697)

Example 14: Of compound 14 Produce

Compound 14 was prepared by the same method as the method of preparing compound 1, except that compounds A3-1 and A3 were used instead of compounds A3 and 2-bromo-9-phenyl-9H-carbazole. (29.4 g, yield 62%; MS:[M+H] ⁺ =599)

Example 15: Of compound 15 Produce

Compound 15 was prepared in the same manner as the method of preparing compound 1, except that compounds A7-1 and A7 were used instead of compounds A3 and 2-bromo-9-phenyl-9H-carbazole. (32.3 g, yield 69%; MS:[M+H] ⁺ =567)

[ Experimental example ]

Experimental example One

A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 130 nm was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode prepared as described above, the following HI-1 compound was thermally vacuum deposited to a thickness of 5 nm to form a hole injection layer. The following HT-1 compound was thermally vacuum deposited on the hole injection layer to a thickness of 25 nm to form a hole transport layer, and the following HT-2 compound was vacuum deposited on the HT-1 deposited film to a thickness of 5 nm to form an electron blocking layer. Subsequently, on the HT-2 deposition film, the compound 1 prepared above and the following Dp-25 compound were co-deposited at a weight ratio of 88:12 to form a light emitting layer having a thickness of 40 nm. On the light emitting layer, the following ET-1 compound was vacuum-deposited to a thickness of 25 nm to form an electron transport layer, and the following ET-2 compound and LiQ were added in a weight ratio of 98:2 thereon. The electron injection layer was formed by vacuum evaporation (thickness 10 nm). A cathode was formed by depositing aluminum to a thickness of 100 nm on the electron injection layer.

[ Experimental example ]

Experimental example One

A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 130 nm was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode prepared as described above, the following HI-1 compound was thermally vacuum deposited to a thickness of 5 nm to form a hole injection layer. The following HT-1 compound was thermally vacuum deposited on the hole injection layer to a thickness of 25 nm to form a hole transport layer, and the following HT-2 compound was vacuum deposited on the HT-1 deposited film to a thickness of 5 nm to form an electron blocking layer. Subsequently, on the HT-2 deposition film, the compound 1 prepared above and the following Dp-25 compound were co-deposited at a weight ratio of 88:12 to form a light emitting layer having a thickness of 40 nm. On the light emitting layer, the following ET-1 compound was vacuum-deposited to a thickness of 25 nm to form an electron transport layer, and the following ET-2 compound and LiQ were added in a weight ratio of 98:2 thereon. The electron injection layer was formed by vacuum evaporation (thickness 10 nm). A cathode was formed by depositing aluminum to a thickness of 100 nm on the electron injection layer.

It was the deposition rate of the organic material in the above process, maintaining a 0.04nm / sec to about 0.07nm / sec, aluminum was deposited at a rate of 0.2nm / sec, During the deposition, a vacuum 1 × 10 ^-7 torr to 5 × 10 ^- Maintained ⁸ torr.

Experimental example 2 to 21 and Comparative example 1 to 9

Organic light-emitting devices of Experimental Examples 2 to 15 and Comparative Examples 1 to 6 were manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in Experimental Example 1.

In Experimental Examples 16 to 21 and Comparative Examples 7 to 9, an organic light emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used in a weight ratio of 1:1 instead of Compound 1. Taking Experimental Example 16 as an example, instead of Compound 1 in Experimental Example 1, Compound 1 and Compound E-2 were used in a weight ratio of 1:1.

10 mA/cm ² in the organic light emitting device of the Experimental Examples and Comparative Examples Voltage, efficiency, light emission color, and lifetime were measured when the current density was applied, and the results are shown in Table 1 below. At this time, T ₉₅ refers to the time required to reduce the luminance to 95% when the initial luminance at the current density of 20 mA/cm ² is 100%.

compound Voltage(V)
(@10mA/cm ² ) Efficiency (cd/A)
(@10mA/cm ² ) Luminous color T ₉₅
(@20mA/cm ² ) Experimental Example 1 One 3.01 65.9 green 59 Experimental Example 2 2 3.00 65.8 green 60 Experimental Example 3 3 3.06 66.6 green 69 Experimental Example 4 4 2.97 66.1 green 59 Experimental Example 5 5 2.89 64.0 green 66 Experimental Example 6 6 2.84 66.1 green 69 Experimental Example 7 7 3.11 67.2 green 68 Experimental Example 8 8 2.98 67.9 green 60 Experimental Example 9 9 2.92 66.9 green 65 Experimental Example 10 10 3.05 68.0 green 58 Experimental Example 11 11 3.03 65.9 green 61 Experimental Example 12 12 3.04 63.5 green 69 Experimental Example 13 13 2.98 64.9 green 62 Experimental Example 14 14 2.94 63.1 green 70 Experimental Example 15 15 3.01 66.2 green 71 Comparative Example 1 C1 3.01 60.0 green 45 Comparative Example 2 C2 3.07 62.5 green 51 Comparative Example 3 C3 3.11 59.5 green 62 Comparative Example 4 C4 3.06 59.2 green 60 Comparative Example 5 C5 3.12 61.2 green 61 Comparative Example 6 C6 3.09 60.9 green 63 Experimental Example 16 1, E-2 3.29 72.1 green 160 Experimental Example 17 4, E-2 3.20 74.8 green 169 Experimental Example 18 6, E-2 3.28 74.0 green 161 Experimental Example 19 10, E-2 3.32 74.7 green 165 Experimental Example 20 11, E-2 3.48 74.9 green 169 Experimental Example 21 15, E-2 3.26 74.1 green 171 Comparative Example 7 C2, E-2 3.14 58.9 green 66 Comparative Example 8 C4, E-2 3.50 65.0 green 138 Comparative Example 9 C6, E-2 3.48 65.9 green 141

Experimental Examples 1 to 15 and Comparative Examples 1 to 6 are device examples using a single host for the light emitting layer.

Compounds C1 to C3 used in Comparative Examples 1 to 3 are compounds in which only an aryl group and one benzothiazole and benzoxazole are substituted with a 3,3' bonded biscarbazole. The device examples of Experimental Examples 14 to 15 from Table 1 are compounds in which symmetric benzothiazole and benzoxazole are substituted with 3,3' bonded biscarbazole. Compared to Comparative Examples 1 to 3, it can be seen that the life characteristics are about 15% to 58% superior.

The compounds used in Comparative Examples 4 to 6 are compounds in which only an aryl group and dibenzothiophene are substituted for biscarbazole having a bond other than 3,3'. In Table 1, the compounds used in the device examples of Experimental Examples 1 to 13 are compounds in which one benzothiazole and benzoxazole are substituted with biscarbazole having a bond other than 3,3'. Compared to Comparative Examples 4 to 6, it can be seen that the lifetime characteristics are about 9% to 15% superior.

Experimental Examples 16 to 21 are device examples in which two types of hosts are used in the light emitting layer. Comparing Experimental Examples 16 to 21 and Experimental Examples 1 to 15, it can be seen that when two types of hosts are used in the light emitting layer, the efficiency is higher, and in particular, the lifespan characteristics are greatly improved.

Even when two types of hosts are used for the light emitting layer, it can be seen that the devices of Examples 16 to 21 using the compound of the present invention have superior current efficiency and lifetime characteristics compared to the devices of Comparative Examples 7 to 9.

In the compound represented by Formula 1 of the present invention, benzothiazole and benzoxazole, which have electronic properties, are directly bonded to biscarbazole, which has strong hole properties. Accordingly, it can be understood that the compound represented by Formula 1 of the present invention has advantages in terms of efficiency and lifespan of the device, as the inflow of holes and electrons is smooth and the balance between holes and electrons is well matched due to the structural characteristics.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: electron blocking layer
8: electron transport layer
9: electron injection layer

Claims (12)

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

In Formula 1,
Any one of R1 to R4 is directly bonded to any one of R5 to R8 of the following formula (2),
R10 is hydrogen or a substituted or unsubstituted aryl group, m is an integer of 0 to 4, and when m is 2 or more, R10 is the same as or different from each other,
[Formula 2]

In Formulas 1 and 2,
When R3 and R7 are bonded, Ar1 and Ar2 are the same as each other, and are represented by the following formula (3),
When any one of R1 to R4 and any one of R5, R6 and R8 are bonded, or when any one of R7 and R1, R2 and R4 is bonded, at least one of Ar1 and Ar2 is represented by the following formula 3, and formula 3 Other than Ar1 or Ar2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
The substituent which does not bond among R1 to R8 is hydrogen,
R11 is hydrogen or a substituted or unsubstituted aryl group, n is an integer of 0 to 4, and when n is 2 or more, R11 is the same as or different from each other,
[Formula 3]

In Formula 3, X is O or S,
R12 is hydrogen or a substituted or unsubstituted aryl group, o is an integer of 0 to 4, and when o is 2 or more, R12 is the same as or different from each other,
remind

Means a position bonded to Formula 1 or 2. The method according to claim 1, wherein the compound represented by Formula 1 is a compound represented by the following Formula 1-1:
[Formula 1-1]

For Formula 1-1,
At least one of Ar1 and Ar2 is represented by Formula 3,
Ar1 or Ar2 other than Formula 3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. The compound of claim 1, wherein the compound represented by Formula 1 is represented by the following Formula 1-2:
[Formula 1-2]

In Formula 1-2,
At least one of Ar1 and Ar2 is represented by Formula 3,
Ar1 or Ar2 other than Formula 3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. The compound of claim 1, wherein the compound represented by Formula 1 is represented by any one of the following Formulas 1-3 to 1-5:
[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Formulas 1-3 to 1-5, the definitions of Ar1 and Ar2 are the same as in Formula 1. The compound of claim 1, wherein the compound represented by Formula 1 is represented by any one of the following Formulas 1-6 to 1-8:
[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Formulas 1-6 to 1-8, the definitions of Ar1 and Ar2 are the same as in Formula 1. The method according to claim 1, wherein Ar1 or Ar2 other than Formula 3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a compound that is a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms. The compound of claim 1, wherein the compound of Formula 1 is selected from the following structural formulas:

The compound of claim 1, wherein the compound of Formula 1 is selected from the following structural formulas:

A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 8 device. The organic light-emitting device of claim 9, wherein the organic material layer includes an emission layer, and the emission layer includes the compound. The method according to claim 9, wherein the organic material layer comprises a light emitting layer, the light emitting layer comprises the compound of Formula 1 as a first host, further comprises a second host,
The light emitting layer is an organic light emitting device comprising a first host and a second host in a weight ratio of 2:1 to 1:2. The organic light emitting device of claim 11, wherein the second host is represented by the following Formula A:
[Formula A]

In Formula A, Ar10 and Ar11 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

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