KR102573175B1 - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device using the same.

Description

Novel compound and organic light emitting device using the same

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, and a fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

An organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.

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

Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a compound represented by Formula 1 below:

[Formula 1]

In Formula 1,

L, L' and L ₁ to L ₄ are each independently a single bond; or a substituted or unsubstituted C _6-60 arylene;

Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing one or more heteroatoms of N, O and S,

R ₁ and R ₂ are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-60 Alkyl; or a substituted or unsubstituted C _6-60 aryl;

n and m are each independently an integer from 0 to 2;

However, n + m is 1 to 3,

a is an integer from 0 to 4-m;

b is an integer from 0 to 6-n;

When each of n, m, a and b is 2 or more, the substituents in parentheses are the same as or different from each other.

In addition, the present invention is a first electrode; a second electrode provided to face the first electrode; and 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 represented by Chemical Formula 1. .

The compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics of an organic light emitting device.

1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron injection and transport layer 5 and a cathode 6.
2 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron blocking layer 8, a light emitting layer 4, a hole blocking layer 9, an electron injection and transport layer ( 5) and an example of an organic light emitting element composed of a cathode 6 is shown.

Hereinafter, in order to aid understanding of the present invention, it will be described in more detail.

(Definition of Terms)

는 다른 치환기에 연결되는 결합을 의미한다.In this specification, and

means a bond connected to another substituent.

In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; cyano group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; Alkyl thioxy group; Arylthioxy group; an alkyl sulfoxy group; aryl sulfoxy groups; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; Aralkenyl group; Alkyl aryl group; Alkylamine group; Aralkylamine group; heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl containing at least one of N, O, and S atoms, or substituted or unsubstituted with two or more substituents linked to each other among the substituents exemplified above. . For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with an aryl group having 6 to 25 carbon atoms or a straight-chain, branched-chain or cyclic chain alkyl group having 1 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group is specifically a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. but not limited to

In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.

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

In the present specification, the alkyl group may be straight-chain or branched-chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group 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 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. 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, adamantyl, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthryl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted, etc. However, it is not limited thereto.

In the present specification, heteroaryl is a heteroaryl containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. Examples of the heteroaryl include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridyl group, Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group, indole group, Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadiazolyl group group, a phenothiazinyl group and a dibenzofuranyl group, but are not limited thereto.

In the present specification, an aralkyl group, an aralkenyl group, an alkylaryl group, an arylamine group, and an aryl group among arylsilyl groups are the same as the examples of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the examples of the above-mentioned alkyl group. In the present specification, the description of the above-described heteroaryl may be applied to the heteroaryl among heteroarylamines. In the present specification, the alkenyl group among the aralkenyl groups is the same as the examples of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of heteroaryl described above may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied, except that the hydrocarbon ring is formed by combining two substituents. In the present specification, the heterocyclic group is not a monovalent group, and the description of the above-described heteroaryl may be applied, except that it is formed by combining two substituents.

(compound)

Meanwhile, the present invention provides a compound represented by Formula 1 above.

Specifically, the compound represented by Formula 1 is benzo [b] naphtho [1,8-ef] [1,4] dioxepin (benzo [b] naphtho [1,8-ef] [1,4] dioxepine ) A compound in which an amino group is bonded to the benzene ring of the core, and is characterized in that one or two amino groups may optionally be bonded to the naphthalene ring of the core.

A compound having such a structure exhibits improved hole transport capability and improved thermal stability by having the above structure, and accordingly, an organic light emitting device employing the compound has high efficiency, low driving voltage and long lifespan compared to conventional organic light emitting devices. can represent the characteristics of

Specifically, the compound may be represented by any one of Formulas 1A to 1C:

[Formula 1A]

[Formula 1B]

[Formula 1C]

In Formulas 1A to 1C,

L, L', L ₁ to L ₄ , Ar ₁ to Ar ₄ , R ₁ , R ₂ , n, m, a and b are as defined in Formula 1 above.

More specifically, the compound represented by Formula 1A may be represented by Formula 1A' below:

[Formula 1A']

In Formula 1A',

L, L ₁ , L ₂ , Ar ₁ , Ar ₂ , R ₁ and a are as defined in Formula 1 above,

Z ₁ to Z ₆ are each independently R ₂ ;

One of Z ₁ to Z ₆ is a substituent represented by the following formula (a), and the others are each independently R ₂ ; or

Two of Z ₁ to Z ₆ are each independently a substituent represented by the following formula (a), and the others may each independently be R ₂ ;

[Formula a]

In the above formula (a),

L', L ₃ , L ₄ , Ar ₃ and Ar ₄ are as defined in Formula 1 above.

For example, in Formula 1A',

Z ₁ to Z ₆ are each independently R ₂ ;

Z ₁ is a substituent represented by Formula (a), and Z ₂ to Z ₆ are each independently R ₂ ;

Z ₂ is a substituent represented by Formula (a), and Z ₁ and Z ₃ to Z ₆ are each independently R ₂ ;

Z ₃ is a substituent represented by Formula (a), Z ₁ , Z ₂ and Z ₄ to Z ₆ are each independently R ₂ ;

Z ₄ is a substituent represented by Formula (a), and Z ₁ to Z ₃ , Z ₅ and Z ₆ are each independently R ₂ ;

Z ₅ is a substituent represented by Formula (a), and Z ₁ to Z ₄ and Z ₆ are each independently R ₂ ; or

Z ₆ is a substituent represented by Formula (a), and Z ₁ to Z ₅ may each independently represent R ₂ .

In addition, the compound represented by Formula 1B may be represented by Formula 1B' below:

[Formula 1B']

In Formula 1B',

L, L ₁ , L ₂ , Ar ₁ , Ar ₂ , R ₁ and a are as defined in Formula 1 above,

Z ₁ to Z ₆ are each independently R ₂ ;

One of Z ₁ to Z ₆ is a substituent represented by Formula (a), and the others are each independently R ₂ ; or

Two of Z ₁ to Z ₆ are each independently a substituent represented by Formula (a), and the others may each independently be R ₂ .

For example, in Formula 1B',

Z ₁ to Z ₆ are each independently R ₂ ;

Z ₁ is a substituent represented by Formula (a), and Z ₂ to Z ₆ are each independently R ₂ ;

Z ₂ is a substituent represented by Formula (a), and Z ₁ and Z ₃ to Z ₆ are each independently R ₂ ;

Z ₃ is a substituent represented by Formula (a), Z ₁ , Z ₂ and Z ₄ to Z ₆ are each independently R ₂ ;

Z ₄ is a substituent represented by Formula (a), and Z ₁ to Z ₃ , Z ₅ and Z ₆ are each independently R ₂ ;

Z ₅ is a substituent represented by Formula (a), and Z ₁ to Z ₄ and Z ₆ are each independently R ₂ ; or

Z ₆ is a substituent represented by Formula (a), and Z ₁ to Z ₅ may each independently represent R ₂ .

In addition, the compound represented by Formula 1C may be represented by Formula 1C' below:

[Formula 1C']

In Formula 1C',

L', L ₃ , L ₄ , Ar ₃ , Ar ₄ , R ₂ and b are as defined in Formula 1 above,

Z ₇ to Z ₁₀ are each independently R ₁ ;

One of Z ₁ to Z ₆ is a substituent represented by Formula b below, and the others are each independently R ₁ ; or

Two of Z ₁ to Z ₆ are each independently a substituent represented by Formula (b), and the others may each independently be R ₁ ;

[Formula b]

In the formula b,

L, L ₁ , L ₂ , Ar ₁ , Ar ₂ , R ₁ and a are as defined in Formula 1 above.

For example, in Formula 1C',

Z ₇ to Z ₁₀ are each independently R ₁ ;

Z ₇ is a substituent represented by Formula b, and Z ₈ to Z ₁₀ are each independently R ₁ ;

Z ₈ is a substituent represented by Formula b, and Z ₇ , Z ₉ and Z ₁₀ are each independently R ₁ ;

Z ₉ is a substituent represented by Formula b, and Z ₇ , Z ₈ and Z ₁₀ are each independently R ₁ ; or

Z ₁₀ is a substituent represented by Formula b, and Z ₇ to Z ₉ may each independently represent R ₁ .

In Formula 1, L and L' may each independently represent a single bond, unsubstituted, or deuterium-substituted C _6-20 arylene.

Specifically, L and L' may each independently represent a single bond, phenylene, biphenyldiyl, or naphthylene.

More specifically, L and L' may each independently be a single bond or any one selected from the group consisting of:

.

.

For example, L and L' are both single bonds; L and L' are both phenylene; Or one of L and L' is a single bond, and the other may be any one selected from the group consisting of:

.

.

In addition, in Formula 1, L ₁ to L ₄ may each independently be a single bond, phenylene, biphenyldiyl, or naphthylene.

More specifically, L ₁ to L ₄ may each independently be a single bond or any one selected from the group consisting of:

.

.

For example, L ₁ and L ₂ are both single bonds; One of L ₁ and L ₂ may be a single bond, and the other may be any one selected from the group consisting of:

.

.

Also, for example, L ₃ and L ₄ are both single bonds; One of L ₃ and L ₄ may be a single bond, and the other may be any one selected from the group consisting of:

.

.

Further, in Formula 1, Ar ₁ to Ar ₄ are each independently C _6-20 aryl, dibenzofuranyl, or dibenzothiophenyl;

Here, Ar ₁ to Ar ₄ may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C _1-10 alkyl and C _6-20 aryl.

Specifically, Ar ₁ to Ar ₄ are each independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, triphenylenyl, fluorenyl, dibenzofuranyl, or dibenzothiophenyl. ego,

Here, Ar ₁ to Ar ₄ are unsubstituted or one or more substituents selected from the group consisting of deuterium, C _1-10 alkyl and C _6-20 aryl, for example, deuterium, methyl, ethyl, propyl, It may be substituted with one or more substituents selected from the group consisting of isopropyl, butyl, tert-butyl and phenyl.

More specifically, Ar ₁ to Ar ₄ are each independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenylnaphthyl, phenanthryl, triphenylenyl, fluorenyl, 9,9-dimethyl fluorenyl, 9,9-diphenylfluorenyl, dibenzofuranyl, or dibenzothiophenyl.

For example, Ar ₁ to Ar ₄ may each independently be any one selected from the group consisting of, but is not limited thereto:

.

.

In this case, Ar ₁ and Ar ₂ may be the same as each other. Alternatively, Ar ₁ and Ar ₂ may be different.

의 개수를 의미하는 n은 0, 1, 또는 2이고, 치환기

의 개수를 의미하는 m은 0, 1, 또는 2일 수 있다. 이때, n+m은 1, 2, 또는 3일 수 있다. Also, substituents

n, which means the number of, is 0, 1, or 2, and the substituent

m, meaning the number of, may be 0, 1, or 2. In this case, n+m may be 1, 2, or 3.

Alternatively, n may be 0 or 1, m may be 0 or 1, and n+m may be 1 or 2.

In this case, when n and m are both 1, L ₁ and L ₃ are equal to each other, L ₂ and L ₄ are equal to each other, Ar ₁ and Ar ₃ are equal to each other, and Ar ₂ and Ar ₄ are equal to each other. can

In addition, R ₁ and R ₂ may each independently represent hydrogen or deuterium.

More specifically, R ₁ and R ₂ may both be hydrogen or both deuterium.

In addition, which means the number of R ₁ a is an integer from 0 to 4-m, for example, when m is 0, a is 0, 1, 2, 3, or 4, and when m is 1, a is 0, 1, 2, or 3 .

In addition, which means the number of R ₂ b is an integer from 0 to 6-n, for example, when n is 0, b is 0, 1, 2, 3, 4, 5, or 6, and when n is 1, b is 0, 1, 2 , 3, 4, or 5.

In addition, the compound may be represented by any one of Formulas 1A-1 to 1A-5, 1B-1, 1C-1 and 1C-2:

In Formulas 1A-1 to 1A-5, 1B-1, 1C-1 and 1C-2,

L, L', L ₁ to L ₄ and Ar ₁ to Ar ₄ are as defined in Formula 1 above.

On the other hand, representative examples of the compound represented by Formula 1 are as follows:

.

Meanwhile, when n is 0, m is 1, and L is a single bond, the compound represented by Chemical Formula 1 can be prepared by a preparation method as shown in Scheme 1 below. The manufacturing method may be more specific in Preparation Examples to be described later.

[Scheme 1]

In Scheme 1, X is halogen, preferably bromo or chloro, and other substituents are defined as described above.

Specifically, the compound represented by Chemical Formula 1 is prepared by combining starting materials SM1 and SM2 through an amine substitution reaction. It is preferable to carry out this amine substitution reaction in the presence of a palladium catalyst and a base, and a reactor for the reaction may be appropriately changed.

In addition, when n is 0, m is 1, and L is not a single bond, the compound represented by Formula 1 can be prepared by a preparation method shown in Scheme 2 below. The manufacturing method may be more specific in Preparation Examples to be described later.

[Scheme 2]

In Scheme 2, X is halogen, preferably bromo or chloro, and definitions of other substituents are as described above.

Specifically, the compound represented by Chemical Formula 1 is prepared by combining starting materials SM3 and SM4 through a Suzuki-Coupling reaction. It is preferable to carry out this Suzuki-Coupling reaction in the presence of a palladium catalyst and a base, and a reactor for the reaction may be appropriately changed.

Other unexemplified compounds represented by Formula 1 can be prepared by appropriately modifying starting materials with reference to Schemes 1 and 2 above.

(organic light emitting device)

Meanwhile, the present invention provides an organic light emitting device including the compound represented by Formula 1 above. In one example, the present invention provides 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 compound represented by Chemical Formula 1. .

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer as organic material layers. However, the structure of the organic light emitting device is not limited thereto and may include fewer organic layers.

In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 above. Contains the indicated compounds.

Also, the organic material layer may include a light emitting layer, and the light emitting layer includes the compound represented by Chemical Formula 1.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention further includes a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, and an electron transport layer and an electron injection layer between the light emitting layer and the second electrode, in addition to the light emitting layer as an organic material layer. can have a structure that However, the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.

In addition, the organic light emitting device according to the present invention has a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate, wherein the first electrode is an anode and the second electrode is a cathode. may be minor. In addition, the organic light emitting device according to the present invention has an inverted type organic layer in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate, wherein the first electrode is a cathode and the second electrode is an anode. It may be a light emitting device. For example, the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .

1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron injection and transport layer 5 and a cathode 6. In this structure, the compound represented by Chemical Formula 1 may be included in the hole transport layer.

2 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron blocking layer 8, a light emitting layer 4, a hole blocking layer 9, an electron injection and transport layer ( 5) and an example of an organic light emitting element composed of a cathode 6 is shown. In this structure, the compound represented by Formula 1 may be included in the hole injection layer, the hole transport layer, or the electron suppression layer.

The organic light emitting device according to the present invention may be manufactured with materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by Chemical Formula 1. Also, 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 according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, depositing a metal or a metal oxide having conductivity or an alloy thereof on the substrate to form an anode 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 represented by Chemical 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 means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

As the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material 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); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function so as to facilitate electron injection into the organic material layer. Specific examples of the anode 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 for injecting holes from the electrode, and the hole injection material has the ability to transport holes and has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and generated in the light emitting layer A compound that prevents migration of excitons to the electron injecting layer or electron injecting material and has excellent thin film formation ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic matter, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light emitting layer, and has high hole mobility. material is suitable. As the hole transport material, the compound represented by Formula 1, or an arylamine-based organic material, a conductive polymer, and a block copolymer having both a conjugated and a non-conjugated part may be used, but is not limited thereto. .

The electron blocking layer is formed on the hole transport layer, and is preferably provided in contact with the light emitting layer to control hole mobility and prevent excessive movement of electrons to increase hole-electron coupling probability, thereby increasing the efficiency of the organic light emitting device. means a layer that serves to improve The electron blocking layer includes an electron blocking material, and as an example of the electron blocking material, a compound represented by Chemical Formula 1 or an arylamine-based organic material may be used, but is not limited thereto.

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.

As described above, the light emitting layer may include a host material and a dopant material. The host material may further include a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periplanthene, etc. having an arylamino group, and styrylamine compounds include substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, wherein one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but is not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

The hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to improve the efficiency of the organic light emitting device by controlling electron mobility and preventing excessive movement of holes to increase the probability of hole-electron coupling layers that play a role. The hole blocking layer includes a hole blocking material, and examples of the hole blocking material include azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; A compound having an electron withdrawing group such as a phosphine oxide derivative may be used, but is not limited thereto.

The electron injection and transport layer is a layer that simultaneously serves as an electron transport layer and an electron injection layer for injecting electrons from an electrode and transporting the received electrons to the light emitting layer, and is formed on the light emitting layer or the hole blocking layer. As such an electron injecting and transporting material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Examples of specific electron injection and transport materials include Al complexes of 8-hydroxyquinoline; Complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes; triazine derivatives, etc., but are not limited thereto. Or fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds , Or may be used together with nitrogen-containing 5-membered ring derivatives, etc., but is not limited thereto.

The electron injection and transport layer may also be formed as a separate layer such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the light emitting layer or the hole blocking layer, and the above-described electron injection and transport material may be used as an electron transport material included in the electron transport layer. In addition, the electron injection layer is formed on the electron transport layer, and examples of electron injection materials included in the electron injection layer include LiF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, Thiophyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like can be used.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. 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 side emission type depending on the material used.

In addition, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

Preparation of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

[Production Example]

Preparation Example A: Preparation of Intermediate Compound A

Compound sub 1, naphthalene-1,8-diol (20.00 g, 125.00 mmol), and compound sub 2, 1-bromo-2,3-difluorobenzene (22.92 g, 137.50 mmol) was completely dissolved in 230 mL of DMF, K ₂ CO ₃ (69.11 g, 500.00 mmol) was added, and the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, DMF was concentrated under reduced pressure and recrystallized with 250 mL of ethyl acetate to prepare Compound A (28.47 g, yield: 73%).

MS[M+H] ⁺ = 314

Preparation Example B: Preparation of Intermediate Compound B

Intermediate compound B was prepared in the same manner as in Preparation Example A, except that sub 3 was used instead of sub 1 in Preparation Example A.

MS[M+H] ⁺ = 314

Preparation Example C: Preparation of Intermediate Compound C

Intermediate Compound C was prepared in the same manner as in Preparation Example A, except that sub 4 and sub 5 were used instead of sub 1 and sub 2 in Preparation Example A.

MS[M+H] ⁺ = 314

Preparation Example D: Preparation of Intermediate Compound D

Intermediate compound D was prepared in the same manner as in Preparation Example A, except that sub 6 and sub 5 were used instead of sub 1 and sub 2 in Preparation Example A.

MS[M+H] ⁺ = 314

Preparation Example E: Preparation of Intermediate Compound E

Intermediate compound E was prepared in the same manner as in Preparation Example A, except that sub 4 and sub 6 were used instead of sub 1 and sub 2 in Preparation Example A.

MS[M+H] ⁺ = 391

Preparation Example F: Preparation of Intermediate Compound F

Intermediate compound E was prepared in the same manner as in Preparation Example A, except that sub 7 and sub 6 were used instead of sub 1 and sub 2 in Preparation Example A.

MS[M+H] ⁺ = 391

Preparation Example 1: Preparation of Compound 1

After completely dissolving compound A (6.25 g, 19.97 mmol) and compound a-1 (8.72 g, 21.96 mmol) in 330 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, NaOtBu (2.49 g, 25.96 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.20 g, 0.40 mmol), the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 250 mL of ethyl acetate to prepare Compound 1 (7.74 g, yield: 62%).

MS[M+H] ⁺ = 630

Preparation Example 2: Preparation of Compound 2

After completely dissolving compound B (6.53 g, 20.86 mmol) and compound a-2 (9.66 g, 22.95 mmol) in 320 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, NaOtBu (2.61 g, 27.12 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.21 g, 0.42 mmol), the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 310 mL of ethyl acetate to prepare Compound 2 (9.94 g, yield: 56%).

MS[M+H] ⁺ = 654

Preparation Example 3: Preparation of Compound 3

After completely dissolving compound C (6.88 g, 21.98 mmol) and compound a-3 (10.18 g, 24.18 mmol) in 320 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, NaOtBu (2.75 g, 28.58 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.22 g, 0.44 mmol), the mixture was heated and stirred for 6 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 340 mL of ethyl acetate to prepare compound 3 (8.81 g, yield: 61%).

MS[M+H] ⁺ = 654

Preparation Example 4: Preparation of Compound 4

After completely dissolving compound D (7.13 g, 22.78 mmol) and compound a-4 (10.30 g, 25.06 mmol) in 320 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, NaOtBu (2.85 g, 29.61 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.23 g, 0.46 mmol), the mixture was heated and stirred for 7 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 270 mL of ethyl acetate to prepare Compound 4 (7.95 g, yield: 54%).

MS[M+H] ⁺ = 644

Preparation Example 5: Preparation of Compound 5

After completely dissolving compound A (6.13 g, 19.58 mmol) and compound a-5 (7.44 g, 21.54 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere, 2M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis-(triphenylphosphine)palladium (0.68 g, 0.59 mmol), the mixture was heated and stirred 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 350 mL of ethyl acetate to prepare Compound 5 (9.26 g, 75%).

MS[M+H] ⁺ = 630

Preparation Example 6: Preparation of Compound 6

After completely dissolving compound B (6.55 g, 20.93 mmol) and compound a-6 (9.09 g, 23.02 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere, 2M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis-(triphenylphosphine)palladium (0.73 g, 0.63 mmol), the mixture was heated and stirred 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 340 mL of ethyl acetate to prepare compound 6 (8.88 g, 62%).

MS[M+H] ⁺ = 680

Preparation Example 7: Preparation of Compound 7

After completely dissolving compound C (6.49 g, 20.73 mmol) and compound a-7 (7.87 g, 22.81 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere, 2M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis-(triphenylphosphine)palladium (0.72 g, 0.62 mmol), the mixture was heated and stirred 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 310 mL of ethyl acetate to prepare compound 7 (7.93 g, 61%).

MS[M+H] ⁺ = 630

Preparation Example 8: Preparation of Compound 8

After completely dissolving compound D (5.98 g, 19.11 mmol) and compound a-8 (8.85 g, 21.02 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere, 2M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis-(triphenylphosphine)palladium (0.66 g, 0.57 mmol), the mixture was heated and stirred 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 420 mL of ethyl acetate to prepare Compound 8 (10.07 g, 75%).

MS[M+H] ⁺ = 706

Preparation Example 9: Preparation of Compound 9

After completely dissolving compound B (6.48 g, 20.70 mmol) and compound a-9 (11.36 g, 22.77 mmol) in 300 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, NaOtBu (2.59 g, 26.91 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.21 g, 0.41 mmol), the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 360 mL of ethyl acetate to prepare compound 9 (9.11 g, yield: 60%).

MS[M+H] ⁺ = 732

Preparation Example 10: Preparation of Compound 10

After completely dissolving compound B (7.34 g, 23.45 mmol) and compound a-10 (10.09 g, 25.80 mmol) in 300 mL of xylene in a 500 mL round bottom flask in a nitrogen atmosphere, NaOtBu (2.93 g, 30.49 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.24 g, 0.47 mmol), the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 280 mL of ethyl acetate to prepare Compound 10 (7.87 g, yield: 54%).

MS[M+H] ⁺ = 624

Preparation Example 11: Preparation of Compound 11

After completely dissolving compound E (5.26 g, 16.81 mmol) and compound a-11 (7.74 g, 35.29 mmol) in 300 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, NaOtBu (4.04 g, 42.01 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.34 g, 0.67 mmol), the mixture was heated and stirred for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 280 mL of ethyl acetate to prepare Compound 11 (7.13 g, yield: 63%).

MS[M+H] ⁺ = 669

Preparation Example 12: Preparation of Compound 12

After completely dissolving compound F (5.55 g, 17.73 mmol) and compound a-12 (11.01 g, 37.24 mmol) in 300 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, NaOtBu (4.26 g, 44.33 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.36 g, 0.71 mmol), the mixture was heated and stirred for 7 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 250 mL of ethyl acetate to prepare Compound 12 (8.36 g, yield: 57%).

MS[M+H] ⁺ = 821

Preparation Example 13: Preparation of Compound 13

After completely dissolving compound E (5.11 g, 13.04 mmol) and compound a-13 (8.29 g, 28.68 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere, 2M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis-(triphenylphosphine)palladium (0.90 g, 0.78 mmol), the mixture was heated and stirred 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 340 mL of ethyl acetate to prepare Compound 13 (7.44 g, 79%).

MS[M+H] ⁺ = 721

Example 1-1

A glass substrate coated with ITO (indium tin oxide) to a thickness of 1,000 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum deposition machine.

A hole injection layer was formed by thermally vacuum-depositing the following compound HI1 and the following compound HI2 to a thickness of 100 Å in a ratio of 98:2 (molar ratio) on the ITO transparent electrode prepared as described above. Compound 4 prepared in Preparation Example 4 was vacuum deposited on the hole injection layer to a thickness of 1150 Å to form a hole transport layer. Subsequently, an electron blocking layer was formed on the hole transport layer by vacuum depositing a compound of EB1 to a film thickness of 50 Å.

Subsequently, a compound represented by Chemical Formula BH and a compound represented by Chemical Formula BD were vacuum deposited at a weight ratio of 25:1 to form a light emitting layer on the electron blocking layer to a film thickness of 200 Å.

A hole blocking layer was formed on the light emitting layer by vacuum depositing a compound represented by Chemical Formula HB1 to a film thickness of 50 Å. Subsequently, a compound represented by Chemical Formula ET1 and a compound represented by Chemical Formula LiQ were vacuum deposited at a weight ratio of 1:1 on the hole-blocking layer to form an electron injection and transport layer with a thickness of 310 Å. A negative electrode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

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 on the cathode was 0.3Å / sec, and the deposition rate of aluminum was 2Å / sec, and the vacuum level during deposition was 2ⅹ10 ^-7 ~ Maintaining 5x10 ^-6 torr, an organic light emitting device was manufactured.

Examples 1-2 to 1-5

An organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compounds shown in Table 1 were used instead of the compounds of Preparation Example 1. At this time, the structures of the compounds used in the above examples are summarized as follows.

.

.

Comparative Examples 1-1 to 1-3

An organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compounds shown in Table 1 were used instead of the compounds of Preparation Example 1. At this time, the structures of the compounds HT1, HT2 and HT3 used in Table 1 are as follows.

Experimental Example 1

When current was applied to the organic light emitting devices prepared in Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 means the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(hole transport layer) Voltage
(V
@10mA/cm ² ) efficiency
(cd/A
@10mA/cm ² ) color seat 4
(x,y4 T95
(hr) Example 1-1 compound 4 4.40 6.25 (0.147, 0.144) 245 Example 1-2 compound 8 4.43 6.21 (0.146, 0.145) 250 Example 1-3 compound 10 4.30 6.48 (0.147, 0.146) 275 Example 1-4 compound 11 4.31 6.49 (0.147, 0.145) 265 Example 1-5 compound 12 4.32 6.47 (0.146, 0.145) 270 Comparative Example 1-1 HT1 4.92 5.61 (0.147, 0.145) 85 Comparative Example 1-2 HT2 4.81 5.92 (0.145, 0.145) 205 Comparative Example 1-3 HT3 5.00 5.81 (0.145, 0.146) 180

As shown in Table 1, the organic light emitting device of the example using the compound represented by Formula 1 as a material for the hole transport layer exhibited excellent characteristics in all of driving voltage, luminous efficiency, and lifetime compared to the organic light emitting device of the comparative example.

Specifically, the organic light emitting device of the above embodiment has a diamine structure and employs HT1 HT2 and HT3 materials, respectively, which are often used as conventional hole transport layer materials. Compared to the organic light emitting devices of Comparative Examples 1-1 to 1-3, It can be seen that while having a driving voltage, it exhibits improved efficiency and significantly longer lifespan.

Example 2-1 to Example 2-7

Except for using the HI compound instead of Compound 4 prepared in Preparation Example 4 as the hole transport layer in Example 1-1 and using the compound shown in Table 2 instead of Compound EB1 as the electron suppression layer, An organic light emitting device was manufactured in the same manner as in Example 1-1. At this time, the structures of the compounds used in the above examples are summarized as follows.

.

.

Comparative Examples 2-1 and 2-2

An organic light emitting device was manufactured in the same manner as in Example 2-1, except that the compounds shown in Table 2 were used instead of the compound of Example 2-1. At this time, the structures of the compounds of the compounds EB2 and EB3 used in Table 2 are as follows.

Experimental Example 2

When current was applied to the organic light emitting devices prepared in the above Examples and Comparative Examples, voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in Table 2 below. T95 means the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(electron suppression layer) Voltage
(V@
10 mA/cm ² ) efficiency
(cd/A
@10mA/cm ² ) color coordinates
(x,y) T95
(hr) Example 2-1 compound 1 4.32 6.71 (0.145, 0.145) 255 Example 2-2 compound 2 4.30 6.70 (0.144, 0.144) 250 Example 2-3 compound 3 4.33 6.69 (0.146, 0.145) 245 Example 2-4 compound 5 4.47 6.67 (0.145, 0.144) 240 Example 2-5 compound 6 4.48 6.58 (0.144, 0.144) 235 Example 2-6 compound 7 4.59 6.51 (0.146, 0.145) 235 Examples 2-7 compound 9 4.59 6.53 (0.145, 0.144) 240 Comparative Example 2-1 EB2 4.84 6.11 (0.145, 0.146) 195 Comparative Example 2-2 EB3 5.11 5.85 (0.146, 0.144) 160

As shown in Table 2, the organic light emitting device of the example using the compound represented by Formula 1 as the electron suppression layer material exhibited excellent characteristics in all of driving voltage, luminous efficiency and lifetime compared to the organic light emitting device of the comparative example.

Specifically, the organic light emitting device of the above embodiment is compared to the organic light emitting devices of Comparative Examples 2-1 and 2-2 employing materials of EB2 and EB3, which have a diamine structure and are often used as conventional electron suppression layer materials, respectively It can be confirmed that while having a low driving voltage, improved efficiency and significantly longer lifespan are exhibited.

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

Claims (11)

A compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
L, L' and L ₁ to L ₄ are each independently a single bond; or a substituted or unsubstituted C _6-60 arylene;
Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing one or more heteroatoms of N, O and S,
R ₁ and R ₂ are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-60 Alkyl; or a substituted or unsubstituted C _6-60 aryl;
n and m are each independently an integer from 0 to 2;
However, n + m is 1 to 3,
a is an integer from 0 to 4-m;
b is an integer from 0 to 6-n;
However, the following compounds are excluded from the compounds represented by Formula 1,
.
According to claim 1,
The compound is represented by any one of the following formulas 1A to 1C,
compound:
[Formula 1A]

[Formula 1B]

[Formula 1C]

In Formulas 1A to 1C,
L, L', L ₁ to L ₄ , Ar ₁ to Ar ₄ , R ₁ , R ₂ , n, m, a and b are as defined in claim 1.
According to claim 1,
L and L' are each independently a single bond, or any one selected from the group consisting of,
compound:

.
According to claim 1,
L ₁ to L ₄ are each independently a single bond, phenylene, biphenyldiyl, or naphthylene;
compound.
According to claim 1,
Ar ₁ to Ar ₄ are each independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenylnaphthyl, phenanthryl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, dibenzofuranyl, or dibenzothiophenyl;
compound.
According to claim 5,
Ar ₁ to Ar ₄ are each independently any one selected from the group consisting of
compound:

.
According to claim 1,
R ₁ and R ₂ are each independently hydrogen or deuterium;
compound.
According to claim 1,
n+m is 1 or 2;
compound.
According to claim 1,
The compound is represented by any one of Formulas 1A-1 to 1A-5, 1B-1, 1C-1 and 1C-2,
compound:

In Formulas 1A-1 to 1A-5, 1B-1, 1C-1 and 1C-2,
L, L', L ₁ to L ₄ and Ar ₁ to Ar ₄ are as defined in claim 1.
According to claim 1,
The compound is any one selected from the group consisting of the following compounds,
compound:

.
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 compound according to any one of claims 1 to 10. That is, an organic light emitting element.