KR102244880B1 - Organic light emitting device - Google Patents

Abstract

The present specification is a positive electrode; In an organic light emitting device comprising a cathode and an organic material layer including at least one emission layer provided between the anode and the cathode, the emission layer is a first host represented by Formula 1, represented by Formula 1-1 or Formula 1-2 It provides an organic light-emitting device including a second host and a dopant, and including a layer including a compound represented by Formula 2 between the anode and the emission layer.

Description

Organic light emitting device{ORGANIC LIGHT EMITTING DEVICE}

The present specification relates to an organic light emitting device.

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 electrons injected from the two electrodes are combined in the organic thin film to form a pair and then emit light while extinguishing. The organic thin film may be composed of a single layer or multiple layers as necessary.

Materials used in organic light-emitting devices are pure organic materials or complex compounds in which organic materials and metals form a complex, and depending on the use, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. It can be classified as Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state upon oxidation is mainly used. Meanwhile, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state at the time of reduction is mainly used. In addition, a material having a stable form in both oxidized and reduced states is preferable as the material for the emission layer, and a material with high luminous efficiency that converts excitons to light when holes and electrons are recombined in the emission layer is formed. desirable.

Korean Patent Publication No. 10-2014-001568

An object of the present specification is to provide an organic light emitting device having high luminous efficiency, low driving voltage, and long life.

An exemplary embodiment of the present invention is a positive electrode; In an organic light emitting device comprising a cathode and an organic material layer including at least one light emitting layer provided between the anode and the cathode,

The emission layer includes a first host represented by Formula 1 below, a second host represented by Formula 1-1 or Formula 1-2, and a dopant,

It provides an organic light emitting device including a layer containing a compound represented by the following formula (2) between the anode and the light emitting layer.

[Formula 1]

[Formula 1-1]

[Formula 1-2]

[Formula 2]

In Formulas 1, 1-1, 1-2 and 2,

X1 is O or S,

X2 is O, S or N(Ra),

R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 to L6 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing one or more of S, O and N,

Ar4 to Ar7 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,

Ar8 and Ra are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,

a, b and e are each an integer of 0 to 6,

c and d are each an integer of 0 to 7,

When a, b, c, d, and e are each 2 or more, the substituents in parentheses are the same as or different from each other.

In addition, according to an exemplary embodiment of the present invention, the layer containing the compound represented by Formula 2 above provides an organic light emitting device that is a hole transport layer.

The exemplary embodiments of the present invention include a first host, a second host, and a dopant in the emission layer of the organic light emitting device, and include the compound represented by Formula 2 in the organic material layer between the anode and the emission layer, thereby providing excellent efficiency and low driving voltage. And it provides an organic light emitting device having a long life characteristics.

1 is a diagram showing an organic light emitting device of the present invention.

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

The present invention is a positive electrode; In an organic light-emitting device comprising a cathode and an organic material layer including at least one light-emitting layer provided between the anode and the cathode, the light-emitting layer is a first host represented by Formula 1 below, Formula 1-1 or 1-2 It provides an organic light-emitting device comprising a second host represented by and a dopant, and including a layer including a compound represented by the following formula (2) between the anode and the emission layer.

[Formula 1]

[Formula 1-1]

[Formula 1-2]

[Formula 2]

In Formulas 1, 1-1, 1-2 and 2,

X1 is O or S,

X2 is O, S or N(Ra),

R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 to L6 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing one or more of S, O and N,

Ar4 to Ar7 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,

Ar8 and Ra are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,

a, b and e are each an integer of 0 to 6,

c and d are each an integer of 0 to 7,

When a, b, c, d, and e are each 2 or more, the substituents in parentheses are the same as or different from each other.

The present invention includes a first host represented by Formula 1, a second host represented by Formula 1-1 or 1-2, and a dopant represented by Formula 1 in an emission layer of an organic light emitting device, and represented by Formula 2 between the anode and the emission layer. By including the layer containing the compound, it is possible to manufacture an organic light emitting device having a low driving voltage, excellent lifespan characteristics, and high efficiency.

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.

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

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 at which 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; Cyano group (-CN); A nitro group (-NO ₂ ); A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group substituted with one or two or more substituents selected from the group consisting of, or two or more of the above-exemplified substituents is 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.

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

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

Spirofluorenyl groups such as,

(9,9-dimethylfluorenyl group), and

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

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si, and Se as hetero atoms, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group. And the like, but are not limited to these.

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

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

The organic light-emitting device of the present invention includes a first host represented by Formula 1, a second host represented by Formula 1-1 or 1-2, and a dopant in the emission layer.

The second host may be included in an amount of 25 to 400 parts by weight based on 100 parts by weight of the first host, and according to another example, it may be included in an amount of 100 to 200 parts by weight. When the second host is included in the above range to manufacture an organic light-emitting device, it is possible to obtain an organic light-emitting device having high luminous efficiency, a low driving voltage, and a long lifespan.

The dopant may be included in 6 parts by weight to 20 parts by weight based on 100 parts by weight of the host material in the emission layer.

L1 and L2 in Formula 1 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present invention, the L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group.

In another exemplary embodiment, L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted C6 to C30 arylene group.

According to another exemplary embodiment, the L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 30 carbon atoms unsubstituted or substituted with a heteroaryl group having 2 to 30 carbon atoms.

In another exemplary embodiment, L1 and L2 are the same as or different from each other, and each independently a direct bond; A phenylene group unsubstituted or substituted with a C2-C30 heteroaryl group; A biphenylene group unsubstituted or substituted with a heteroaryl group having 2 to 30 carbon atoms; A terphenylene group unsubstituted or substituted with a heteroaryl group having 2 to 30 carbon atoms; Or a naphthylene group unsubstituted or substituted with a C2-C30 heteroaryl group.

According to another exemplary embodiment, the L1 and L2 are the same as or different from each other, and each independently a direct bond; A phenylene group unsubstituted or substituted with a carbazole group; A biphenylene group unsubstituted or substituted with a carbazole group; A terphenylene group unsubstituted or substituted with a carbazole group; Or a naphthylene group unsubstituted or substituted with a carbazole group.

In another exemplary embodiment, L1 and L2 are the same as or different from each other, and each independently a direct bond; It is a phenylene group unsubstituted or substituted with a carbazole group.

According to an exemplary embodiment of the present invention, R1 in Formula 1 is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C20 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In another exemplary embodiment, R1 is hydrogen.

According to an exemplary embodiment of the present invention, a is an integer of 0 to 2.

In another exemplary embodiment, a is 0 or 1.

According to an exemplary embodiment of the present invention, Ar2 of Formula 1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or substituted or unsubstituted S, O, and N is a heterocyclic group having 2 to 60 carbon atoms including one or more.

In another exemplary embodiment, Ar2 in Formula 1 is a heterocyclic group having 2 to 60 carbon atoms including at least one of substituted or unsubstituted S, O, and N.

According to another exemplary embodiment, Ar2 of Formula 1 is a heterocyclic group having 2 to 30 carbon atoms including at least one of substituted or unsubstituted S, O, and N.

In another exemplary embodiment, Ar2 is a heterocyclic group having 2 to 30 carbon atoms including 1 or more substituted or unsubstituted N.

According to an exemplary embodiment of the present invention, Ar2 may be represented by any one of the following Chemical Formulas 1-A to 1-J.

[Formula 1-A]

[Formula 1-B]

[Formula 1-C]

[Formula 1-D]

[Formula 1-E]

[Formula 1-F]

[Formula 1-G]

[Formula 1-H]

[Formula 1-I]

[Formula 1-J]

In the formulas 1-A to 1-J,

X3 to X10 are the same as or different from each other, and each independently O, S, N(Rb) or C(Rc)(Rd),

Rb, Rc, Rd, R11 to R21, R and R'are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

n1 is an integer from 0 to 8,

n2 is an integer from 0 to 7,

n3 is an integer from 0 to 5,

n4, n6 to n9 and n11 are each an integer of 0 to 10,

n5 and n10 are each an integer of 0 to 9,

When n1 to n11 are each 2 or more, the substituents in parentheses are the same as or different from each other,

* Means the position bonded to L2.

According to an exemplary embodiment of the present invention, n1 is an integer of 0 to 2.

According to an exemplary embodiment of the present invention, R11 is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In another exemplary embodiment, R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

According to another exemplary embodiment, R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted carbazole group.

In another exemplary embodiment, R11 is hydrogen; heavy hydrogen; Aryl group having 6 to 30 carbon atoms; Or a C 2 to C 30 heteroaryl group unsubstituted or substituted with a C 6 to C 30 aryl group.

According to another exemplary embodiment, R11 is hydrogen; heavy hydrogen; Phenyl group; Biphenyl group; Naphthyl group; Or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present invention, n2 and n3 are integers of 0 to 2, respectively.

In an exemplary embodiment of the present invention, R12 and R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

According to an exemplary embodiment of the present invention, R12 and R13 are hydrogen.

In an exemplary embodiment of the present invention, n4 to n11 are integers of 0 to 2.

According to an exemplary embodiment of the present invention, the R14 to R21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

According to an exemplary embodiment of the present invention, the R14 to R21 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, the R14 to R21 are the same as or different from each other, and each independently hydrogen; Or a phenylene group.

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

In another exemplary embodiment, R and R'are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group.

According to an exemplary embodiment of the present invention, X3 to X10 are the same as or different from each other, and are each independently O, S, N(Rb) or C(Rc)(Rd).

According to an exemplary embodiment of the present invention, Rb is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Rb is a substituted or unsubstituted phenyl group.

According to an exemplary embodiment of the present invention, Rc and Rd are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In another exemplary embodiment, Rc and Rd are substituted or unsubstituted methyl groups.

According to an exemplary embodiment of the present invention, Ar1 in Formula 1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing one or more of S, O and N.

In another exemplary embodiment, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or substituted or unsubstituted S, O, and N is a heterocyclic group having 2 to 30 carbon atoms including one or more.

According to another exemplary embodiment, Ar1 is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms including at least one of S, O, and N.

In another exemplary embodiment, Ar1 is a substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted phenanthroline group; Or a substituted or unsubstituted benzoimidazole group.

According to an exemplary embodiment of the present invention, Ar1 may be represented by any one of the following Chemical Formulas Ar-1 to Ar-5.

[Formula Ar-1]

[Formula Ar-2]

[Formula Ar-3]

[Formula Ar-4]

[Formula Ar-5]

In the formulas Ar-1 to Ar-5,

W1 to W12 are the same as or different from each other, and each independently C(Re) or N,

Re, Rf, and A1 to A4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

p1 and p2 are each an integer of 0 to 5,

p3 is an integer from 0 to 4,

p4 is an integer from 0 to 7,

When p1 to p4 are each 2 or more, the substituents in parentheses are the same as or different from each other,

* Means the position bonded to L1.

According to an exemplary embodiment of the present invention, W1 to W12 are the same as or different from each other, and each independently C(Re) or N.

In an exemplary embodiment of the present invention, Re, Rf, and A1 to A4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

According to an exemplary embodiment of the present invention, Rf is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

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

According to another exemplary embodiment, Re and A1 to A4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In another exemplary embodiment, Re and A1 to A4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of a cyano group (-CN), a nitro group (-NO _{2) and an alkyl group having 1 to 20 carbon atoms;} Or a cyano group (-CN), a nitro group (-NO ₂ ), and a C2 to C30 heteroaryl group substituted or unsubstituted with one or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, the Re and A1 to A4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with one or more selected from the group consisting of a cyano group (-CN), a nitro group (-NO _{2 ), and a methyl group;} A biphenyl group unsubstituted or substituted with one or more selected from the group consisting of a cyano group (-CN), a nitro group (-NO _{2 ), and a methyl group;} A naphthyl group unsubstituted or substituted with one or more selected from the group consisting of a cyano group (-CN), a nitro group (-NO _{2 ), and a methyl group;} A terphenyl group unsubstituted or substituted with one or more selected from the group consisting of a cyano group (-CN), a nitro group (-NO _{2 ), and a methyl group;} A fluorenyl group unsubstituted or substituted with one or more selected from the group consisting of a cyano group (-CN), a nitro group (-NO _{2 ), and a methyl group;} A dibenzofuran group unsubstituted or substituted with one or more selected from the group consisting of a cyano group (-CN), a nitro group (-NO _{2) and a methyl group;} Or a cyano group (-CN), a nitro group (-NO ₂ ), and a dibenzothiophene group unsubstituted or substituted with one or more selected from the group consisting of a methyl group.

According to an exemplary embodiment of the present invention, p1 to p4 are integers of 0 to 2, respectively.

In an exemplary embodiment of the present invention, Formula 1 may be represented by any one of the following structures.

The organic material layer of the organic light emitting device of the present invention includes a second host represented by Formula 1-1 or 1-2.

In an exemplary embodiment of the present invention, L3 is a direct bond; Or a substituted or unsubstituted C6 to C30 arylene group.

According to another exemplary embodiment, L3 is a direct bond.

According to an exemplary embodiment of the present invention, Ar3 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or substituted or unsubstituted S, O, and N is a heterocyclic group having 2 to 30 carbon atoms including one or more.

In an exemplary embodiment of the present invention, Ar3 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present invention, Ar3 is an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with a methyl group.

In another exemplary embodiment, Ar3 is a phenyl group unsubstituted or substituted with a methyl group; A biphenyl group unsubstituted or substituted with a methyl group; A naphthyl group unsubstituted or substituted with a methyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.

According to another exemplary embodiment, Ar3 is a phenyl group; Biphenyl group; Naphthyl group; Or 9,9-dimethylfluorenyl group.

According to an exemplary embodiment of the present invention, X1 is O or S, and X2 is O, S or N(Ra).

According to an exemplary embodiment of the present invention, Ra is a substituted or unsubstituted aryl group.

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

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

According to an exemplary embodiment of the present invention, L4 is a direct bond; Or a substituted or unsubstituted C6 to C30 arylene group.

According to another embodiment, L4 is a substituted or unsubstituted phenylene group.

According to an exemplary embodiment of the present nickname, b, c, and d are integers of 0 to 2, respectively.

According to an exemplary embodiment of the present invention, the R2 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In another exemplary embodiment, R2 to R4 are hydrogen.

According to an exemplary embodiment of the present invention, Formula 1-1 may be any one of the following structures.

According to an exemplary embodiment of the present invention, Formula 1-2 may be any one of the following structures.

The organic light emitting device of the present invention includes a dopant in the light emitting layer. Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamino group, and the styrylamine compound is substituted or unsubstituted As a compound in which at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The organic light-emitting device of the present invention includes a layer containing the compound represented by Formula 2 between the anode and the emission layer.

In an example of the present invention, the compound represented by Formula 2 includes two amine groups in the compound, and the layer including the compound represented by Formula 2 may be a hole transport layer. When the hole transport layer contains a compound having 3 or more amine groups, a compound having 3 or more amine groups has a HOMO energy level of about ~5.2 eV, which is too high to increase the energy barrier between the electron-suppressing layer and the light-emitting layer, resulting in a charge balance. ) Is out of balance, deteriorating the characteristics of the device.

The organic light-emitting device prepared by including the compound of Formula 2 may have better efficiency than the organic light-emitting device prepared by including the compound containing three or more amine groups.

According to an exemplary embodiment of the present invention, Ar8 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another exemplary embodiment, Ar8 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Ar8 is an aryl group having 6 to 30 carbon atoms, which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

In another exemplary embodiment, Ar8 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted fluorenyl group.

According to another exemplary embodiment, Ar8 is a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Or 9,9-dimethylfluorenyl group.

According to an exemplary embodiment of the present invention, L5 and L6 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group.

According to another exemplary embodiment, L5 and L6 are the same as or different from each other, and each independently a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In another exemplary embodiment, L5 and L6 are the same as or different from each other, and each independently a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted terphenylene group.

According to an exemplary embodiment of the present invention, Ar4 to Ar7 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, Ar4 to Ar7 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another exemplary embodiment, Ar4 to Ar7 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted naphthyl group.

According to an exemplary embodiment of the present invention, R5 is hydrogen.

According to an exemplary embodiment of the present invention, e is an integer of 0 to 2.

In an exemplary embodiment of the present invention, Formula 2 may be represented by any one of the following structures.

The compounds of Formulas 1, 1-1, 1-2, and 2 according to an exemplary embodiment of the present specification may be prepared as in Preparation Examples described below, and the compounds of Formulas 1, 1-1, 1-2, and 2 are The core structure may be manufactured as in the following Preparation Example. Substituents may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention is an organic material layer, a hole injection layer, a hole transport layer, a layer that simultaneously injects and transports holes, a hole control layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously injects and transports electrons. , May have a structure including an electron suppression layer, and the like. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic material layers.

The organic light emitting device of the present invention may include the compound represented by Chemical Formula 2 in the hole transport layer.

The organic light-emitting device according to an exemplary embodiment of the present invention may be a normal type organic light-emitting device in which an anode, one or more organic material layers including an emission layer, and a cathode are sequentially stacked on a substrate.

The organic light emitting device according to another exemplary embodiment may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers including an emission layer, and an anode 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/Anode

(2) Anode/Hole Injection Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(3) Anode/Hole Injection Layer/Hole Buffer Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(4) Anode/Hole Transport Layer/Light-Emitting Layer/Electron Transport Layer/Anode

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

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

(7) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode

(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode

(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(10) Anode/hole transport layer/electron suppression layer/light-emitting layer/electron transport layer/cathode

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

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

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

(14) Anode/Hole Transport Layer/Light-Emitting Layer/Hole Suppression Layer/Electron Transport Layer/Anode

(15) Anode/Hole Transport Layer/Light-Emitting Layer/Hole Suppression Layer/Electron Transport Layer/Electron Injection Layer/Anode

(16) Anode/Hole Injection Layer/Hole Transport Layer/Light-Emitting Layer/Hole Suppression Layer/Electron Transport Layer/Anode

(17) Anode/Hole injection layer/Hole transport layer/Light-emitting layer/Hole suppression layer/Electron transport layer/Electron injection layer/Anode

(18) Anode/Hole Injection Layer/Hole Transport Layer/Electron Suppression Layer/Light-Emitting Layer/Hole Blocking Layer/Layer for Simultaneous Electron Injection and Electron Transport/Anode

(19) Anode/Hole Injection Layer/Hole Transport Layer/Electron Suppression Layer/Emitting Layer/Layer for Simultaneous Electron Injection and Electron Transport/Anode

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

For example, the structure of an organic light emitting device according to an exemplary embodiment of the present invention is illustrated in FIG. 1.

1 is a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron suppression layer (5), a light emitting layer (6), a hole blocking layer (7), electron injection and electron transport. The structure of the organic light emitting device in which the layer 8 and the cathode 9 are sequentially stacked at the same time is illustrated. In such a structure, the compound represented by Formula 1 and the compound represented by Formula 1-1 or 1-2 may be included in the light emitting layer 6, and the compound represented by Formula 2 is included in the hole transport layer 4 Can be included. The emission layer may emit green light.

The organic light-emitting device of the present invention may be manufactured by a conventional method and material for producing an organic light-emitting device, except that one or more organic material layers are formed by using the above-described compounds.

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

For example, the organic light-emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and uses a metal or conductive metal oxide or alloy thereof on a substrate. Is deposited to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a hole control layer, a light emitting layer, an electron transport layer, etc. is formed thereon through a vacuum deposition method or a solution coating method, and can be used as a cathode thereon. It can be made by depositing a material. 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.

The positive electrode is an electrode for injecting holes, and a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer as the positive electrode material. Specific examples of the anode 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: a combination of a metal and an 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 cathode is an electrode for injecting electrons, and it is preferable that the cathode material is a material having a small work function so that electrons can be easily injected 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 multilayered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer, and the hole injection material is a material capable of well injecting holes from the anode at a low voltage. It is preferable that molecular orbital) 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 porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. There are organic substances of, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto, and may be doped with a benzonitrile-based organic substance at a concentration of 0.1 to 10 wt%. The thickness of the hole injection layer may be 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing deterioration of the hole injection characteristics, and when the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There is an advantage that can be prevented.

The hole transport layer may serve to facilitate transport of holes. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer and transferring them to the light emitting layer, and a material having high mobility for holes is suitable. Specific examples include, but are not limited to, the compound represented by Formula 2 of the present invention, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. The thickness of the hole transport layer may be 1 to 100 nm.

A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.

An electron suppressing layer may be provided between the hole transport layer and the light emitting layer. The electron inhibiting layer may be formed of the above-described spiro compound, an arylamine-based organic material, or a material known in the art.

The emission layer may emit red, green, or blue light, and may include a host and a dopant. One or more types of the host may be included, and Formula 1 of the present invention as a first host and Formula 1-1 or 1-2 as a second host. In addition, the compound that can be included as a dopant of the light emitting layer is as described above.

A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and the hole blocking layer is a layer that 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 electron transport layer may play a role of facilitating transport of electrons. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq _3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing deterioration of the electron transport characteristics, and if the thickness of the electron transport layer is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in the driving voltage to improve the movement of electrons. There is an advantage to be able to.

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

The electron injection and electron transport layer may be formed of an electron injection material and/or an electron transport material.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-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 organic light-emitting device according to the present invention may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

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

< Manufacturing example >

Manufacturing example 1-1: Preparation of compound 1-1

Compound 1-a (13.05g, 23.69mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-) in a 500 ml round bottom flask in a nitrogen atmosphere. 1,3,5-triazine) (5.50g, 20.60mmol) was completely dissolved in 240ml of tetrahydrofuran, and 2M aqueous potassium carbonate solution (120ml) was added, followed by tetrakis-(triphenylphosphine)palladium (0.71g, 0.62). mmol) was added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of tetrahydrofuran to prepare compound 1-1 (8.75g, 65%).

MS: [M+H] ⁺ = 657

Manufacturing example 1-2: Preparation of compound 1-2

Compound 1-a (8.31g, 15.09mmol), 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3, in a 500 ml round bottom flask in a nitrogen atmosphere After completely dissolving 5-triazine (4.50g, 13.12mmol) in 200ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (100ml) was added, and tetrakis-(triphenylphosphine)palladium (0.45g, 0.39mmol) was added. Then, it was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 ml of tetrahydrofuran to prepare compound 1-2 (7.59g, 79%).

MS: [M+H] ⁺ = 733

Manufacturing example 1-3: Preparation of compound 1-3

Compound 1-b (13.50g, 21.54mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.00g, 18.73mmol) in tetrahydrofuran in a 500ml round bottom flask in a nitrogen atmosphere After completely dissolved in 220ml, 2M aqueous potassium carbonate solution (110ml) was added, tetrakis-(triphenylphosphine)palladium (0.65g, 0.56mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 150 ml of tetrahydrofuran to prepare compound 1-3 (9.76g, 71%).

MS: [M+H] ⁺ = 733

Manufacturing example 2-1: Preparation of compound 2-1

Compound 2-a (9.50g, 18.89mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (6.23g, 21.72mmol) was completely added to 240ml of tetrahydrofuran in a 500ml round bottom flask in a nitrogen atmosphere. After dissolving, 2M aqueous potassium carbonate solution (120ml) was added, tetrakis-(triphenylphosphine)palladium (0.65g, 0.57mmol) was added, followed by heating and stirring for 7 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 190 ml of tetrahydrofuran to prepare compound 2-1 (8.16g, 65%).

MS: [M+H] ⁺ = 667

Manufacturing example 2-2: Preparation of compound 2-2

Compound 2-b (8.50g, 14.68mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (4.85g, 16.88mmol) was completely added to 200ml of tetrahydrofuran in a 500ml round bottom flask in a nitrogen atmosphere. After dissolving, 2M aqueous potassium carbonate solution (100ml) was added, tetrakis-(triphenylphosphine)palladium (0.51g, 0.44mmol) was added, followed by heating and stirring for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 170 ml of tetrahydrofuran to prepare compound 2-2 (6.61 g, 61%).

MS: [M+H] ⁺ = 743

Manufacturing example 2-3: Preparation of compound 2-3

Compound 2-b (7.00g, 13.92mmol), (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid in a 500 ml round bottom flask in a nitrogen atmosphere (5.81g, 16.00mmol) was completely dissolved in 200ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (100ml) was added, tetrakis-(triphenylphosphine)palladium (0.48g, 0.42mmol) was added, and then for 5 hours. Heated and stirred. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 150 ml of tetrahydrofuran to prepare compound 2-3 (5.67 g, 55%).

MS: [M+H] ⁺ = 743

Manufacturing example 3-1: Preparation of compound 3-1

Compound 3-a (4.50g, 11.28mmol), (4-(diphenylamino)phenyl) boronic acid (7.17g, 24.81mmol) was completely dissolved in 220ml of tetrahydrofuran in a 500ml round bottom flask in a nitrogen atmosphere, and then 2M carbonic acid. Potassium aqueous solution (110ml) was added, tetrakis-(triphenylphosphine)palladium (0.39g, 0.34mmol) was added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 ml of tetrahydrofuran to prepare compound 3-1 (5.78 g, 70%).

MS: [M+H] ⁺ = 730

Manufacturing example 3-2: Preparation of compound 3-2

Except for using N 3,6-dibromo-9-(naphthalen-2-yl)-9H-carbazole instead of 3-a, compound 3-2 was prepared in the same manner as in the preparation method of compound 3-1. Was prepared.

MS: [M+H] ⁺ = 780

Manufacturing example 3-3: Preparation of compound 3-3

Except for using 9-([1,1'-biphenyl]-4-yl)-3,6-dibromo-9H-carbazole instead of 3-a, the same as the preparation method of compound 3-1 Compound 3-3 was prepared by the method.

MS: [M+H] ⁺ = 806

< Example >

Example 1: Fabrication of an organic light emitting device

A glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000Å 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 manufactured 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 washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

The HI1 compound was formed as a hole injection layer on the prepared ITO transparent electrode to a thickness of 1100Å, but the compound A-1 was p-doped at a concentration of 2%. Compound 3-1 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 350 Å. Subsequently, an electron suppressing layer was formed by vacuum depositing the following EB1 compound having a thickness of 150 Å on the hole transport layer.

Then, on the electron-suppressing layer, a host composition in which Compound 1-1 and the following compound 2-1 are mixed in a weight ratio of 4:6 (Compound 1-1: Compound 2-1), and phosphorescence at 6% by weight of the host composition The following YGD-1 compound, which is a dopant, was vacuum deposited together to form a green light emitting layer having a thickness of 350 Å.

A hole blocking layer was formed by vacuum depositing the following HB1 compound with a film thickness of 50 Å on the emission layer. Subsequently, on the hole blocking layer, the following ET1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 to form a layer for simultaneous electron injection and electron transport at a thickness of 300 Å. Lithium fluoride (LiF) in a thickness of 12 Å and aluminum in a thickness of 1,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7Å/sec, the deposition rate of lithium fluoride at the negative electrode was 0.3Å/sec, and the deposition rate of aluminum was 2Å/sec, and the vacuum degree during deposition was 2x10 ^-7 ~ An organic light emitting device was manufactured by maintaining ^{5x10 -6 torr.}

Example 2 to 10 and Comparative example 1 to 13: Fabrication of an organic light emitting device

Examples 2 to 2 were carried out in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of compounds 3-1 in the hole transport layer and compounds 1-1 and 2-1 in the green light emitting layer, respectively. Organic light emitting devices of 10 and Comparative Examples 1 to 13 were manufactured. At this time, HT1, YGH-1 and YGH-2 shown in Table 1 are the compounds shown above.

Experimental example : Performance evaluation of organic light emitting device

The voltage and efficiency were measured at a current density of ^{10 mA/cm 2} on the organic light emitting devices manufactured in Examples 1 to 10 and Comparative Examples 1 to 13, compared to the initial luminance (6000 nit) at a current density of ^{20 mA/cm 2} _{The lifetime (LT 95} ), which is the time required to decrease to %, was measured, and the results are shown in Table 1 below.

Precision
Transport layer Light emitting layer
(6:4) Voltage
(V) Luminous efficiency
(cd/A) LT ₉₅
(hr) Comparative Example 1 HT1 1-1,YGH-2 4.45 5.95 235 Comparative Example 2 HT1 1-2,YGH-2 4.49 5.94 220 Comparative Example 3 HT1 1-3,YGH-2 4.48 5.93 225 Comparative Example 4 HT1 YGH-1,2-1 4.47 5.92 225 Comparative Example 5 HT1 YGH-1,2-2 4.46 5.96 210 Comparative Example 6 HT1 YGH-1,2-3 4.45 5.97 215 Comparative Example 7 3-1 YGH-1,YGH-2 4.04 6.23 175 Comparative Example 8 3-2 YGH-1,YGH-2 3.95 6.26 170 Comparative Example 9 3-3 YGH-1,YGH-2 4.08 6.24 165 Comparative Example 10 HT1 1-1,2-1 4.46 6.06 255 Comparative Example 11 HT1 1-2,2-2 4.45 6.03 250 Comparative Example 12 HT1 1-3,2-3 4.43 6.06 260 Comparative Example 13 HT1 YGH-1,YGH-2 4.62 5.85 185 Example 1 3-1 1-1,2-1 3.63 6.32 290 Example 2 3-2 1-1,2-2 3.56 6.37 280 Example 3 3-3 1-1,2-3 3.65 6.36 285 Example 4 3-1 1-2,2-1 3.64 6.36 275 Example 5 3-2 1-2,2-2 3.51 6.56 260 Example 6 3-3 1-2,2-3 3.62 6.52 265 Example 7 3-1 1-3,2-1 3.65 6.53 275 Example 8 3-2 1-3,2-2 3.55 6.51 260 Example 9 3-3 1-3,2-3 3.61 6.35 265 Example 10 3-2 1-1,2-1 3.51 6.56 295

Table 1 shows an organic light-emitting device using an existing compound (Comparative Example 13), an organic light-emitting device using a compound represented by Chemical Formula 2 as the hole transport layer, but using an existing compound as a material for the green light-emitting layer (Comparative Example 7). To 9) and the organic light emitting device using the compound represented by Formula 1 and Formula 1-1 or 1-2 as the material for the emission layer, but using the existing compound as the material for the hole transport layer (Comparative Examples 1 to 6 and Comparative Examples The basic characteristics of 10 to Comparative Example 12) are shown.

Comparing Examples and Comparative Examples, when the compounds represented by Formulas 1, 1-1, 1-2 and 2 are used in combination as materials for the green light emitting layer and the hole transport layer, respectively, lower driving than the conventional organic light emitting device It is confirmed to exhibit voltage, high efficiency and long life. In particular, when the compound 3-2 was used as the hole transport layer material, the driving voltage was the lowest and the efficiency was the highest, and when the light emitting layer materials 1-1 and 2-1 were used, the lifetime was the longest.

On the other hand, comparing Comparative Examples 1 to 13, in Comparative Examples 7 to 9 in which the hole transport layer material was changed to the compound represented by Formula 2, the driving voltage was lowered and the luminous efficiency was improved, and the green light emitting layer material was represented by Formula 1 above. In Comparative Examples 1 to 6 and Comparative Examples 10 to 12 changed to any one of the compound and/or Chemical Formulas 1-1 and 1-2, the lifespan was improved. However, it did not show the efficiency and life of the example level.

Accordingly, the organic light emitting device of the present invention includes a compound having a structure in which an arylamine including a linker is substituted on both sides of the carbazole at positions 3 and 6 of the carbazole as shown in Chemical Formula 2 in the hole transport layer between the anode and the light emitting layer. A compound having a structure in which the position 4 of dibenzothiophene having electron stability as shown in Chemical Formula 1 is substituted with a triazine having excellent electron injection ability and thermal stability is used as an n-type material of the green light emitting layer. Low driving voltage and improved efficiency by using a compound having a structure in which carbazole and aryl groups are substituted at positions 4 and 2 of dibenzothiophene as shown in Formulas 1-1 and 1-2 as the p-type material of the green light emitting layer It is confirmed that it shows a long life while showing

1: substrate
2: anode
3: hole injection layer
4: hole transport layer
5: electron suppression layer
6: light emitting layer
7: hole block
8: Layer that simultaneously injects and transports electrons
9: cathode

Claims (11)

anode; In an organic light emitting device comprising a cathode and an organic material layer including at least one light emitting layer provided between the anode and the cathode,
The emission layer includes a first host represented by Formula 1 below, a second host represented by Formula 1-1 or Formula 1-2, and a dopant,
An organic light-emitting device comprising a hole transport layer comprising a compound represented by the following formula (2) between the anode and the light-emitting layer:
[Formula 1]

[Formula 1-1]

[Formula 1-2]

[Formula 2]

In Formulas 1, 1-1, 1-2 and 2,
X1 is O or S,
X2 is O, S or N(Ra),
R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L1 to L6 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing one or more of S, O and N,
Ar4 to Ar7 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,
Ar8 and Ra are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,
a, b and e are each an integer of 0 to 6,
c and d are each an integer of 0 to 7,
When a, b, c, d, and e are each 2 or more, the substituents in parentheses are the same as or different from each other. The method according to claim 1,
The organic light-emitting device of Ar2 is a substituted or unsubstituted heterocyclic group containing at least one of S, O, and N having 2 to 60 carbon atoms. The method according to claim 1,
Ar2 of Formula 1 is an organic light emitting device represented by any one of the following Formulas 1-A to 1-J:
[Formula 1-A]

[Formula 1-B]

[Formula 1-C]

[Formula 1-D]

[Formula 1-E]

[Formula 1-F]

[Formula 1-G]

[Formula 1-H]

[Formula 1-I]

[Formula 1-J]

In the formulas 1-A to 1-J,
X3 to X10 are the same as or different from each other, and each independently O, S, N(Rb) or C(Rc)(Rd),
Rb, Rc, Rd, R11 to R21, R and R'are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
n1 is an integer from 0 to 8,
n2 is an integer from 0 to 7,
n3 is an integer from 0 to 5,
n4, n6 to n9 and n11 are each an integer of 0 to 10,
n5 and n10 are each an integer of 0 to 9,
When n1 to n11 are each 2 or more, the substituents in parentheses are the same as or different from each other,
* Means the position bonded to L2. The method according to claim 1,
Ar1 is an organic light emitting device represented by any one of the following formulas Ar-1 to Ar-5:
[Formula Ar-1]

[Formula Ar-2]

[Formula Ar-3]

[Formula Ar-4]

[Formula Ar-5]

In the formulas Ar-1 to Ar-5,
W1 to W12 are the same as or different from each other, and each independently C(Re) or N,
Re, Rf, and A1 to A4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
p1 and p2 are each an integer of 0 to 5,
p3 is an integer from 0 to 4,
p4 is an integer from 0 to 7,
When p1 to p4 are each 2 or more, the substituents in parentheses are the same as or different from each other,
* Means the position bonded to L1. The method according to claim 1,
The organic light emitting device of Ar3 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms. The method according to claim 1,
Ar8 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in the organic light emitting device. The method according to claim 1,
Formula 1 is an organic light emitting device having any one of the following structures:

. The method according to claim 1,
Formula 1-1 is an organic light emitting device having any one of the following structures:

. The method according to claim 1,
Formula 1-2 is an organic light emitting device having any one of the following structures:

. The method according to claim 1,
Formula 2 is an organic light emitting device having any one of the following structures:

. delete

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