KR102572070B1 - Organic Compound for organic light emitting diode and an organic light emitting diode including the same with High efficiency - Google Patents

Abstract

The present invention relates to a compound for an organic light emitting device and a high-efficiency organic light emitting device including the same, and more particularly, as a hole injection layer material or a hole transport layer material in an organic light emitting device, by including a compound for an organic light emitting device having a specific structure, It relates to a compound for an organic light emitting device exhibiting high efficiency and an organic light emitting device including the same, wherein [Formula A] to [Formula B] are the same as those described in the detailed description of the invention.

Description

Compound for organic light emitting device and high efficiency organic light emitting device including the same {Organic Compound for organic light emitting diode and an organic light emitting diode including the same with High efficiency}

The present invention relates to a compound for an organic light emitting device and a high-efficiency organic light emitting device including the same, and more particularly, as a hole injection layer material or a hole transport layer material in an organic light emitting device, by including a compound for an organic light emitting device having a specific structure, It relates to a compound for an organic light emitting device exhibiting high efficiency and an organic light emitting device including the same.

An organic light emitting diode (OLED) is a display using a self-luminous phenomenon, and has advantages such as a large viewing angle, lightness and compactness compared to liquid crystal displays, and fast response speed. ) Applications to displays or lighting are expected.

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 usually has a structure including an anode, a cathode, and an organic material layer therebetween.

Here, the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, 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. Such an organic light emitting device is known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.

Materials used as the organic layer in the organic light emitting device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc., according to their functions, and electron blocking layers as needed. Alternatively, a hole blocking layer or the like may be added.

As a prior art related to such a hole transport layer, in Patent Registration No. 10-1074193 (published date: 2011.10.14), organic light emission using a compound having a core structure in which at least one benzene ring is condensed in a carbazole structure as a hole transport layer compound A device is disclosed, and in Patent Registration No. 10-1455156 (published date: 2014.10.27), a light emitting auxiliary layer having a HOMO level between the hole transport layer and the light emitting layer between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer A technique related to an organic light emitting device formed is described.

However, despite the attempts of various types of methods for manufacturing organic light emitting devices in the prior art including the prior art, the need for development of organic light emitting devices having more improved luminous efficiency is still continuously required. am.

Registered Patent Publication No. 10-1074193 (Announcement date: 2011.10.14) Registered Patent Publication No. 10-1455156 (Announcement date: 2014.10.27)

Therefore, the technical problem to be achieved by the present invention is to provide a compound for an organic light emitting device having a novel structure, and by including it as a hole injection layer material or a hole transport layer material, an organic light emitting diode having high efficiency characteristics (organic light emitting diode, OLED) is provided.

In order to achieve the above technical problems, the present invention provides a compound for an organic light emitting device represented by the following [Formula A] or [Formula B].

[Formula A]

[Formula B]

In [Formula A] and [Formula B],

The substituents X ₁ and X ₂ are each the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms , Any one selected from a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group,

At least one of the substituents X ₁ and X ₂ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, or a substituted Or an unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms. Any one selected from an arylsilyl group,

The substituents R ₁ to R ₁₀ are each the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted an alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted 5 to 30 carbon atoms An arylthiooxy group, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted A heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, a halogen group, which one,

One or two of the substituents R ₃ to R ₁₀ are substituents represented by the following structural formula A,

When two of R ₃ to R ₁₀ are substituents represented by Structural Formula A, they are the same or different, respectively;

[Structural Formula A]

In the structural formula A,

The linking group L ₁ is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms,

Wherein k is an integer from 1 to 3, when k is 2 or more, each L ₁ is the same as or different from each other;

The substituents R ₁₁ and R ₁₂ are each the same or different, and independently of each other, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted 1 carbon atom to 30 heterocycloalkyl groups, and any one selected from substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms,

The '*' is a binding site to an aromatic carbon atom bonded to any one of the substituents of R ₃ to R ₁₀ ;

In addition, R ₁ and R ₂ may be connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the alicyclic or aromatic monocyclic or polycyclic ring are N, O, P, or Si. , S, Ge, Se, may be substituted with one or more heteroatoms selected from Te;

'Substitution' in 'substituted or unsubstituted' in [Formula A] and [Formula B] is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, and a carbon number 1 to 24 Halogenated alkyl group, C1-24 alkenyl group, C1-24 alkynyl group, C1-24 heteroalkyl group, C6-24 aryl group, C6-24 arylalkyl group, C2-24 hetero Aryl group, C2-24 heteroarylalkyl group, C1-24 alkoxy group, C1-24 alkylamino group, C1-24 arylamino group, C1-24 heteroarylamino group, C1-24 It means that it is substituted with one or more substituents selected from the group consisting of an alkylsilyl group, an arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms.

When the compound for an organic light emitting device according to the present invention is applied to a hole transport layer or a hole injection layer material in an organic light emitting device, an organic light emitting diode (OLED) having excellent device characteristics such as high luminous efficiency and long lifespan can be obtained. can

In particular, when the hole transport layer includes a first hole transport layer using different materials and a second hole transport layer provided between the first hole transport layer and the light emitting layer, and the compound for an organic light emitting device is used in the second hole transport layer It can exhibit characteristics of high luminous efficiency and long life.

1 is a schematic diagram of an organic light emitting device according to one embodiment of the present invention.

Hereinafter, the present invention will be described in more detail. In each drawing of the present invention, the size or dimensions of the structures are enlarged or reduced from the actual ones for clarity of the present invention, and the known configurations are omitted so that the characteristic configurations are revealed, so they are not limited to the drawings. .

In addition, since the size and thickness of each component shown in the drawings are arbitrarily shown for convenience of description, the present invention is not necessarily limited to those shown, and in order to clearly express various layers and regions in the drawings, the thickness is enlarged showed up And in the drawings, for convenience of explanation, the thicknesses of some layers and regions are exaggerated. When a part such as a layer, film, region, plate, etc. is said to be "on" another part, this includes not only the case where it is "directly on" the other part, but also the case where there is another part in the middle.

In addition, throughout the specification, when a certain component is said to "include", it means that it may further include other components without excluding other components unless otherwise stated. Also, throughout the specification, "on" means to be located above or below the target part, and does not necessarily mean to be located on the upper side relative to the direction of gravity.

The present invention may provide a compound for an organic light emitting device represented by the following [Formula A] or [Formula B].

[Formula A]

[Formula B]

In [Formula A] and [Formula B],

The substituents X ₁ and X ₂ are each the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms , Any one selected from a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group,

At least one of the substituents X ₁ and X ₂ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, or a substituted Or an unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms. Any one selected from an arylsilyl group,

The substituents R ₁ to R ₁₀ are each the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted an alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted 5 to 30 carbon atoms An arylthiooxy group, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted A heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, a halogen group, which one,

One or two of the substituents R ₃ to R ₁₀ are substituents represented by the following structural formula A,

When two of R ₃ to R ₁₀ are substituents represented by Structural Formula A, they are the same or different, respectively;

[Structural Formula A]

In the structural formula A,

The linking group L ₁ is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms,

Wherein k is an integer from 1 to 3, when k is 2 or more, each L ₁ is the same as or different from each other;

The substituents R ₁₁ and R ₁₂ are each the same or different, and independently of each other, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted 1 carbon atom to 30 heterocycloalkyl groups, and any one selected from substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms,

The '*' is a binding site to an aromatic carbon atom bonded to any one of the substituents of R ₃ to R ₁₀ ;

In addition, R ₁ and R ₂ may be connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the alicyclic or aromatic monocyclic or polycyclic ring are N, O, P, or Si. , S, Ge, Se, may be substituted with one or more heteroatoms selected from Te;

'Substitution' in 'substituted or unsubstituted' in [Formula A] and [Formula B] is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, and a carbon number 1 to 24 Halogenated alkyl group, C1-24 alkenyl group, C1-24 alkynyl group, C1-24 heteroalkyl group, C6-24 aryl group, C6-24 arylalkyl group, C2-24 hetero Aryl group, C2-24 heteroarylalkyl group, C1-24 alkoxy group, C1-24 alkylamino group, C1-24 arylamino group, C1-24 heteroarylamino group, C1-24 It means that it is substituted with one or more substituents selected from the group consisting of an alkylsilyl group, an arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms.

On the other hand, considering the range of the alkyl or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms" and the "substituted or unsubstituted aryl group having 5 to 50 carbon atoms" in the present invention, the The range of carbon atoms of an alkyl group having 1 to 30 carbon atoms and an aryl group having 5 to 50 carbon atoms refers to the total number of carbon atoms constituting the alkyl part or the aryl part when the substituent is regarded as unsubstituted without considering the substituted part. will be. For example, a phenyl group in which a butyl group is substituted at the para-position should be regarded as corresponding to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

An aryl group, which is a substituent used in the compound of the present invention, is an organic radical derived from an aromatic hydrocarbon by removing one hydrogen. can

Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group, aromatic groups such as pyrenyl group, indenyl group, fluorenyl group, tetrahydronaphthyl group, perylenyl group, chrysenyl group, naphthacenyl group, fluoranthenyl group, and the like, wherein at least one hydrogen atom in the aryl group is a deuterium atom or a halogen atom , A hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH(R), -N(R')(R″), R' and R" are independently of each other having 1 to 10 carbon atoms Alkyl group, in this case referred to as "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, and 1 to 24 carbon atoms of alkenyl group, C1-24 alkynyl group, C1-24 heteroalkyl group, C6-24 aryl group, C6-24 arylalkyl group, C2-24 heteroaryl group or C2-24 It may be substituted with a heteroarylalkyl group.

The heteroaryl group, which is a substituent used in the compound of the present invention, contains 1, 2, or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te, and has 2 to 50 carbon atoms in which the remaining ring atoms are carbon atoms. , preferably a 2 to 24 ring aromatic system, and the rings may be fused to form a ring. In addition, one or more hydrogen atoms of the heteroaryl group may be substituted with the same substituent as that of the aryl group.

In addition, in the present invention, the aromatic heterocycle means that at least one of the aromatic carbons in the aromatic hydrocarbon ring is substituted with a hetero atom, and the aromatic heterocycle preferably has 1 to 3 aromatic carbons in the aromatic hydrocarbon ring being N, O, P, It may be substituted with one or more heteroatoms selected from Si, S, Ge, Se, and Te.

Specific examples of the substituent alkyl group used in the present invention include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, and the like, and one or more of the alkyl groups A hydrogen atom may be substituted with a substituent similar to that of the aryl group.

Specific examples of the cycloalkyl group as a substituent used in the present invention include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, and the like, and at least one hydrogen atom in the cycloalkyl group is the case of the aryl group It can be substituted with the same substituent as

Specific examples of the alkoxy group used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like, One or more hydrogen atoms in the alkoxy group may be substituted with substituents similar to those of the aryl group.

Specific examples of the substituent silyl group used in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl , dimethylfurylsilyl, and the like, and one or more hydrogen atoms in the silyl group may be substituted with the same substituents as in the case of the aryl group.

In the compound for an organic light emitting device represented by [Formula A] or [Formula B] according to the present invention, each of the two aromatic carbon atoms adjacent to the aromatic carbon atom bonded to the oxygen atom in the dibenzofuran ring structure has R ₁ and R ₂ By combining the carbon atom to which is bonded and the carbon atom in the benzene ring including R ₃ to R ₆ , '6-membered ring-5-membered ring containing an oxygen atom-6-membered ring-5 containing a carbon atom to which R ₁ and R ₂ are bonded. Forming an indenodibenzofuran structure including a multi-condensed ring of 'membered ring-6-membered ring', but forming an amine group represented by structural formula A on one or two of the aromatic hydrocarbons of the outer 6-membered ring of the indenodibenzofuran ring ( ) are combined, respectively,

At this time, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms is used as a substituent for at least one of the two centrally located 6-membered aromatic hydrocarbons in the indenodibenzofuran ring. , A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms It is characterized by the fact that substituents such as 30 alkylsilyl groups and substituted or unsubstituted arylsilyl groups having 6 to 30 carbon atoms are bonded. Due to these technical characteristics, in the structure in which an amine group is bonded to an indenodibenzofuran ring, Since the intramolecular electron distribution is localized due to the oxygen atom of the parent skeleton and the nitrogen atom in the amine group, its electron distribution is shifted by adding a substituent such as aryl or heteroaryl to the 6-membered aromatic hydrocarbon ring located in the center of the parent structure. By being stabilized by reconstitution and presumed to express a long lifespan effect, Compared to the conventional organic light emitting device, an organic light emitting device exhibiting high efficiency and long lifespan characteristics can be implemented.

As an embodiment, the substituents R ₁ and R ₂ in the [Formula A] and [Formula B] of the present invention are each the same or different, and independently of each other, an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 18 carbon atoms It may be any one selected from groups, and preferably, the substituents R ₁ and R ₂ are each the same or different, and each independently may be any one substituent selected from methyl or phenyl.

As an example, one of the substituents X ₁ and X ₂ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted carbon atom having 2 to 50 carbon atoms. It is any one selected from a heteroaryl group and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and the other one may be hydrogen or deuterium.

In addition, as an embodiment, at least one of the substituents X ₁ and X ₂ is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 18 carbon atoms, or a substituted or unsubstituted carbon atom having 6 carbon atoms. to 18 aryl groups or substituted or unsubstituted heteroaryl groups having 2 to 20 carbon atoms, preferably one of the substituents X ₁ and X ₂ is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms or a substituted or unsubstituted It is a ringed heteroaryl group having 3 to 20 carbon atoms, and the other one may be hydrogen or deuterium.

In addition, as an embodiment of the present invention, only one of the substituents R ₃ to R ₁₀ in [Formula A] and [Formula B] may be a substituent represented by the structural formula A, and in this case, preferably, the substituent R ₇ may be a substituent represented by Structural Formula A below.

[Structural Formula A]

In this case, R ₁₁ and R ₁₂ are the same or different, and are independently any one selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, , wherein L ₁ and k are as defined above.

In addition, as a specific compound of the compound represented by [Formula A] or [Formula B], it may be any one selected from the group represented by [Compound 1] to [Formula 54].

[Compound 1] [Compound 2] [Compound 3]

[Compound 4] [Compound 5] [Compound 6]

[Compound 7] [Compound 8] [Compound 9]

[Compound 10] [Compound 11] [Compound 12]

[Compound 13] [Compound 14] [Compound 15]

[Compound 16] [Compound 17] [Compound 18]

[Compound 19] [Compound 20] [Compound 21]

[Compound 22] [Compound 23] [Compound 24]

[Compound 25] [Compound 26] [Compound 27]

[Compound 28] [Compound 29] [Compound 30]

[Compound 31] [Compound 32] [Compound 33]

[Compound 34] [Compound 35] [Compound 36]

[Compound 37] [Compound 38] [Compound 39]

[Compound 40] [Compound 41] [Compound 42]

[Compound 43] [Compound 44] [Compound 45]

[Compound 46] [Compound 47] [Compound 48]

[Compound 49] [Compound 50] [Compound 51]

[Compound 52] [Compound 53] [Compound 54]

As a more preferred embodiment of the present invention, the present invention provides a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one compound for an organic light emitting device represented by [Formula A] or [Formula B]. According to these structural features, the organic light emitting device according to the present invention may have high efficiency and/or long lifespan.

In this case, in the present invention, "(the organic layer) contains one or more kinds of organic compounds" means "(the organic layer) includes one organic compound belonging to the scope of the present invention or two or more different kinds belonging to the category of the organic compound. It may contain a compound".

More specifically, the present invention is an anode as a first electrode, a cathode as a second electrode opposite to the first electrode; and an organic layer interposed between the anode and the cathode, wherein the organic layer includes a hole transport layer or a hole injection layer, and the compound for an organic light emitting device according to the present invention may be used for the hole transport layer or the hole injection layer. , The organic layer in the organic light emitting device of the present invention may additionally include at least one of a light emitting layer, a functional layer having a hole injection function and a hole transport function at the same time, an electron transport layer, and an electron injection layer.

That is, the organic light emitting device according to the present invention may include at least one of the organic light emitting device compounds represented by [Formula A] or [Formula B] as a material for a hole transport layer or a hole injection layer in the organic light emitting device. .

More preferably, the organic light emitting device according to the present invention includes an anode as a first electrode and a cathode as a second electrode opposite to the first electrode, and a hole transport layer and a light emitting layer are provided between the anode and the cathode, At this time, the hole transport layer includes a first hole transport layer and a second hole transport layer provided between the first hole transport layer and the light emitting layer, and the first hole transport layer and the second hole transport layer are organic light emitting devices in which different materials are used. In the above, the compound for an organic light emitting device according to the present invention can provide an organic light emitting device characterized in that it is used in the second hole transport layer.

As a more preferred embodiment of the present invention, the organic light emitting device includes a first electrode as an anode, a second electrode as a cathode, a light emitting layer between the anode and the cathode, and a hole injection layer between the anode and the light emitting layer, A first hole transport layer and a second hole transport layer may be sequentially included, and an electron transport layer and an electron injection layer may be sequentially included between the light emitting layer and the cathode.

As an embodiment, in the organic light emitting device according to the present invention, the light emitting layer includes a host and a dopant, and an anthracene derivative represented by Formula C may be used as the host, but is not limited thereto.

[Formula C]

In the above [Formula C].

The substituents R ₁₁ to R ₁₈ are each the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, Substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 2 to 50 carbon atoms Heteroaryl group, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, substituted or unsubstituted An arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms , Any one selected from a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group,

The substituents Ar ₉ and Ar ₁₀ are the same as or different from each other, and independently of each other, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted 3 carbon atoms. It is any one selected from a cycloalkyl group of 30 to 30 and a substituted or unsubstituted heteroaryl group of 2 to 50 carbon atoms;

The linking group L ₁₃ is a single bond, or any one selected from a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms;

Wherein k is an integer from 1 to 3, when k is 2 or more, each L ₁₃ is the same as or different from each other.

As a more specific host compound, Ar ₉ in Formula C may be a substituent represented by Formula C-1 below.

[Formula C-1]

Here, the substituents R ₂₁ to R ₂₅ are the same as or different from each other, and are the same as defined in R ₁ to R ₁₀ described above; It may combine with adjacent substituents to form a saturated or unsaturated ring, in which case the linking group L ₁₃ is a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and k is 1 to 2 An integer of, but when the k is 2 or more, each L ₁₃ is the same as or different from each other.

As an example, the anthracene derivative may be any one selected from the following [Formula 22] to [Formula 60], but is not limited thereto.

<Formula 22> <Formula 23> <Formula 24>

<Formula 25> <Formula 26> <Formula 27>

<Formula 28> <Formula 29> <Formula 30>

<Formula 31> <Formula 32> <Formula 33>

<Formula 34> <Formula 35> <Formula 36>

<Formula 37> <Formula 38> <Formula 39>

<Formula 40> <Formula 41> <Formula 42>

<Formula 43> <Formula 44> <Formula 45>

<Formula 46> <Formula 47> <Formula 48>

<Formula 49> <Formula 50> <Formula 51>

<Formula 52> <Formula 53> <Formula 54>

<Formula 55> <Formula 56> <Formula 57>

<Formula 58> <Formula 59> <Formula 60>

In addition, as a dopant compound used in the light emitting layer in the present invention, at least one compound represented by any one of the following [Formula D1] to [Formula D5] may be included.

[Formula D1]

[Formula D2]

In [Formula D1] and [Formula D2], A ₃₁ , A ₃₂ , E ₁ and F ₁ are each the same or different, and independently of each other, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or It is an unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms;

The two carbon atoms adjacent to each other in the aromatic ring of A ₃₁ and the two carbon atoms adjacent to each other in the aromatic ring of A ₃₂ form a 5-membered ring with the carbon atoms connected to the substituents R ₅₁ and R ₅₂ , respectively. form;

The linking groups L ₂₁ to L ₃₂ are each the same or different, and independently of each other, a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted C6 to 60 carbon atoms It is selected from an arylene group or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;

W is any one selected from NR ₅₃ , CR ₅₄ R ₅₅ , SiR ₅₆ R ₅₇ , GeR ₅₈ R ₅₉ , O, S, and Se;

The substituents R ₅₁ to R ₅₉ and Ar ₂₁ to Ar ₂₈ are the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms A cycloalkenyl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, substituted or unsubstituted alkylamine having 1 to 30 carbon atoms substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, substituted or unsubstituted carbon atoms Any one selected from an alkyl germanium group having 1 to 30, a substituted or unsubstituted aryl germanium group having 1 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group,

The R ₅₁ and R ₅₂ may be connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring are N, O, P, Si, or S. , Ge, Se, may be substituted with one or more heteroatoms selected from Te;

wherein p11 to p14, r11 to r14 and s11 to s14 are each an integer of 1 to 3, and when each of them is 2 or more, the linking groups L ₂₁ to L ₃₂ are the same as or different from each other;

Wherein x1 is an integer of 1 or 2, y1 and z1 are the same or different, and are independently an integer of 0 to 3,

Ar ₂₁ and Ar ₂₂ , Ar ₂₃ and Ar ₂₄ , Ar ₂₅ and Ar ₂₆ , and Ar ₂₇ and Ar ₂₈ may be connected to each other to form a ring;

Two carbon atoms adjacent to each other in the A ₃₂ ring in Formula D1 combine with * in Structural Formula Q ₁₁ to form a condensed ring,

In Chemical Formula D2, two adjacent carbon atoms in the A ₃₁ ring combine with * in Structural Formula Q ₁₂ to form a condensed ring, and two adjacent carbon atoms in the A ₃₂ ring are combined with * in Structural Formula Q ₁₁ and They can combine to form a condensed ring.

[Formula D3]

In the above [Formula D3],

Wherein X ₁ Is any one selected from B, P, P=O

T1 to T3 are the same as or different from each other, and independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms;

Y1 is any one selected from N-R61, CR62R63, O, S, and SiR64R65;

Y2 is any one selected from N-R66, CR66R68, O, S, and SiR69R70;

R61 to R70 are each the same as or different from each other, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted carbon atom A cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted Unsubstituted C1-C30 alkylthioxy group, substituted or unsubstituted C5-C30 arylthioxy group, substituted or unsubstituted C1-C30 alkylamine group, substituted or unsubstituted C5-C30 Any one selected from an arylamine group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, and a halogen group, wherein R61 to R70 are each An alicyclic or aromatic monocyclic or polycyclic ring may be additionally formed by combining with one or more rings selected from T1 to T3.

[Formula D4] [Formula D5]

In [Formula D4] and [Formula D5],

X ₂ is any one selected from B, P, and P=O;

T ₄ to T ₆ are the same as T ₁ to T ₃ in [Formula D3],

The Y ₄ to Y ₆ is the same as the range of Y ₁ to Y ₂ in [Formula D3],

Here, 'substitution' in the 'substituted or unsubstituted' in [Formula D1] to [Formula D5] is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a carbon number 1 -24 halogenated alkyl group, C2-24 alkenyl group, C2-24 alkynyl group, C1-24 heteroalkyl group, C6-24 aryl group, C7-24 arylalkyl group, C2-24 24 heteroaryl group or C2-24 heteroarylalkyl group, C1-24 alkoxy group, C1-24 alkylamino group, C6-24 arylamino group, C1-24 heteroarylamino group, C1 to 24 alkylsilyl groups, arylsilyl groups having 6 to 24 carbon atoms, and aryloxy groups having 6 to 24 carbon atoms.

In addition, in the case of a boron compound represented by any one of [Formula D3] to [Formula D5] among the dopant compounds according to the present invention, as a substituent substitutable for the aromatic hydrocarbon rings or aromatic heterocycles of T1 to T9, Deuterium, an alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, and an arylamino group having 6 to 24 carbon atoms may be substituted, wherein the alkylamino group having 1 to 24 carbon atoms and the carbon number Each alkyl group or aryl group in the 6 to 24 arylamino group may be linked to each other, and more preferred substituents include an alkyl group of 1 to 12 carbon atoms, an aryl group of 6 to 18 carbon atoms, an alkylamino group of 1 to 12 carbon atoms, and a carbon atom group of 6 to 12 carbon atoms. An 18-carbon arylamino group may be substituted, and each of the alkyl or aryl groups in the C1-C12 alkylamino group and the C6-18 arylamino group may be linked to each other.

In addition, as a specific example of a compound represented by any one of [Formula D1] to [Formula D2] among the dopant compounds used in the light emitting layer, any one of the following formulas d1 to formula d239 may be used.

<Formula d1> <Formula d2> <Formula d3>

<Formula d4> <Formula d5> <Formula d6>

<Formula d7><Formulad8><Formulad9>

<Formula d10> <Formula d11> <Formula d12>

<Formula d13> <Formula d14> <Formula d15>

<Formula d16> <Formula d17> <Formula d18>

<Formula d19> <Formula d20> <Formula d21>

<Formula d22> <Formula d23> <Formula d24>

<Formula d25> <Formula d26> <Formula d27>

<Formula d28> <Formula d29> <Formula d30>

<Formula d31><Formulad32><Formulad33>

<Formula d34> <Formula d35> <Formula d36>

<Formula d37> <Formula d38> <Formula d39>

<Formula d40><Formulad41><Formulad42>

<Formula d43><Formulad44><Formulad45>

<Formula d46> <Formula d47> <Formula d48>

<Formula d49> <Formula d50> <Formula d51>

<Formula d52> <Formula d53> <Formula d54>

<Formula d55> <Formula d56> <Formula d57>

<Formula d58> <Formula d59> <Formula d60>

<Formula d61> <Formula d62> <Formula d63>

<Formula d64> <Formula d65> <Formula d66>

<Formula d67> <Formula d68> <Formula d69>

<Formula d70> <Formula d71> <Formula d72>

<Formula d73> <Formula d74> <Formula d75>

<Formula d76> <Formula d77> <Formula d78>

<Formula d79> <Formula d80> <Formula d81>

<Formula d82> <Formula d83> <Formula d84>

<Formula d85> <Formula d86> <Formula d87>

<Formula d88> <Formula d89> <Formula d90>

<Formula d91> <Formula d92> <Formula d93>

<Formula d94> <Formula d95> <Formula d96>

<Formula d97> <Formula d98> <Formula d99>

<Formula d100> <Formula d101> <Formula d102>

<Formula d103> <Formula d104> <Formula d105>

<Formula d106> <Formula d107> <Formula d108>

<Formula d109> <Formula d110> <Formula d111>

<Formula d112> <Formula d113> <Formula d114>

<Formula d115> <Formula d116> <Formula d117>

<Formula d118> <Formula d119> <Formula d120>

<Formula d121> <Formula d122> <Formula d123>

<Formula d124> <Formula d125> <Formula d126>

<Formula d127> <Formula d128> <Formula d129>

<Formula d130> <Formula d131> <Formula d132>

<Formula d133> <Formula d134> <Formula 135>

<Formula d136> <Formula d137> <Formula d138>

<Formula d139> <Formula d140> <Formula d141>

<Formula d142> <Formula d143> <Formula d144>

<Formula d145> <Formula d146> <Formula d147>

<Formula d148> <Formula d149> <Formula d150>

<Formula d151> <Formula d152> <Formula d153>

<Formula d154> <Formula d155> <Formula d156>

<Formula d157> <Formula d158> <Formula d159>

<Formula d160> <Formula d161> <Formula d162>

<Formula d163> <Formula d164> <Formula d165>

<Formula d166> <Formula d167> <Formula d168>

<Formula d169> <Formula d170> <Formula d171>

<Formula d172> <Formula d173> <Formula d174>

<Formula d175> <Formula d176> <Formula d177>

<Formula d178> <Formula d179> <Formula d180>

<Formula d181> <Formula d182> <Formula d183>

<Formula d184> <Formula d185> <Formula d186>

<Formula d187> <Formula d188> <Formula d189>

<Formula d190> <Formula d191> <Formula d192>

<Formula d193> <Formula d194> <Formula d195>

<Formula d196> <Formula d197> <Formula d198>

<Formula d199> <Formula d200> <Formula d201>

<Formula d202> <Formula d203> <Formula d204>

<Formula d205> <Formula d206> <Formula d207>

<Formula d208> <Formula d209> <Formula d210>

<Formula d211> <Formula d212> <Formula d213>

<Formula d214> <Formula d215> <Formula d216>

<Formula d217> <Formula d218> <Formula d219>

<Formula d220> <Formula d221> <Formula d222>

<Formula d223> <Formula d224> <Formula d225>

<Formula d226> <Formula d227> <Formula d228>

<Formula d229> <Formula d230> <Formula d231>

<Formula d232> <Formula d233> <Formula d234>

<Formula d235> <Formula d236> <Formula d237>

<Formula d238> <Formula d239>

Further, in the present invention, the compound represented by [Formula D3] may be any one selected from the following <Formula D 101> to <Formula D133>.

<Formula D 101> <Formula D 102> <Formula D 103>

<Formula D 104> <Formula D 105> <Formula D 106>

<Formula D 107> <Formula D 108> <Formula D 109>

<Formula D 110> <Formula D 111> <Formula D 112>

<Formula D 113> <Formula D 114> <Formula D 115>

<Formula D 116> <Formula D 117> <Formula D 118>

<Formula D 119> <Formula D 120> <Formula D 121>

<Formula D 122> <Formula D 123> <Formula D 124>

<Formula D 125> <Formula D 126> <Formula D 127>

<Formula D 128> <Formula D 129> <Formula D 130>

<Formula D 131> <Formula D 132> <Formula D 133>

Further, in the present invention, the compound represented by any one of [Formula D4] and [Formula D4] may be any one selected from the following <Formula D201> to <Formula D280>.

[Formula D201] [Formula D202] [Formula D203] [Formula D204]

[Formula D205] [Formula D206] [Formula D207] [Formula D208]

[Formula D209] [Formula D210] [Formula D211] [Formula D212]

[Formula D213] [Formula D214] [Formula D215] [Formula D216]

[Formula D217] [Formula D218] [Formula D219] [Formula D220]

[Formula D221] [Formula D222] [Formula D223] [Formula D224]

[Formula D225] [Formula D226] [Formula D227] [Formula D228]

[Formula D229] [Formula D230] [Formula D231] [Formula D232]

[Formula D233] [Formula D234] [Formula D235] [Formula D236]

[Formula D237] [Formula D238] [Formula D239] [Formula D240]

[Formula D241] [Formula D242] [Formula D243] [Formula D244]

[Formula D245] [Formula D246] [Formula D247] [Formula D248]

[Formula D249] [Formula D250] [Formula D251] [Formula D252]

[Formula D253] [Formula D254] [Formula D255] [Formula D256]

[Formula D257] [Formula D258] [Formula D259] [Formula D260]

[Formula D261] [Formula D262] [Formula D263] [Formula D264]

[Formula D265] [Formula D266] [Formula D267] [Formula D268]

[Formula D269] [Formula D270] [Formula D271] [Formula D272]

[Formula D273] [Formula D274] [Formula D275] [Formula D276]

[Formula D277] [Formula D278] [Formula D279] [Formula D280]

In this case, the content of the dopant in the light emitting layer may be typically selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

In addition, the light emitting layer may further include various hosts and various dopant materials in addition to the dopant and the host.

Hereinafter, an organic light emitting device according to an embodiment of the present invention will be described with reference to the drawings.

1 is a diagram showing the structure of an organic light emitting device according to an embodiment of the present invention.

As shown in FIG. 1, the organic light emitting device according to an embodiment of the present invention includes an anode 20, a hole transport layer 40, a light emitting layer 50 including a host and a dopant, an electron transport layer 60, and a cathode ( 80) in sequential order, wherein the anode is used as a first electrode and the cathode is used as a second electrode, including a hole transport layer between the anode and the light emitting layer, and an electron transport layer between the light emitting layer and the cathode. Corresponds to an organic light emitting device.

In addition, the hole transport layer 40 may include a first hole transport layer and a second hole transport layer, respectively, and the second hole transport layer may be positioned between the first hole transport layer and the light emitting layer. Here, as the material for the second hole transport layer in the organic light emitting device of the present invention, a compound for an organic light emitting device represented by Formula A or Formula B according to the present invention may be used, and according to these structural characteristics, the organic light emitting device according to the present invention The light emitting device may have characteristics of high efficiency and long life.

In addition, the organic light emitting device according to the embodiment of the present invention includes a hole injection layer 30 between the anode 20 and the hole transport layer 40, and electron transport layer 60 and the cathode 80 between the electron transport layer An injection layer 70 may be included.

Referring to FIG. 1, the organic light emitting device and the manufacturing method of the present invention are as follows.

First, the anode 20 is formed by coating a material for an anode (anode) electrode on the substrate 10 . Here, as the substrate 10, a substrate used in a typical organic EL device is used, and an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and water resistance is preferable. In addition, as materials for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used.

The hole injection layer 30 is formed by vacuum thermal deposition or spin coating of a hole injection layer material on the anode 20 electrode. Next, the hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of a hole transport layer material on the hole injection layer 30 .

The material of the hole injection layer 30 may include a compound for an organic light emitting device represented by Formula A or Formula B according to the present invention, and may be used without particular limitation as long as it is commonly used in the art, , for example 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine], NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)] , TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N' -bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine], etc. However, the present invention is not necessarily limited thereto.

In addition, as the material of the hole transport layer 40, the compound for an organic light emitting device represented by Formula A or Formula B according to the present invention may be included, and more preferably, the hole transport layer is the first hole transport layer and the second hole transport layer. Including, when the compound for an organic light emitting device represented by Formula A or Formula B is used for the second hole transport layer, as a material used for the first hole transport layer, it corresponds to a material commonly used in the art It is not particularly limited as long as it is, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) Alternatively, N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (a-NPD) and the like can be used. However, the present invention is not necessarily limited thereto.

Subsequently, the light emitting layer 50 may be deposited on the hole transport layer 40 by a vacuum deposition method or a spin coating method.

Here, the light emitting layer 50 may be made of a host and a dopant, and materials constituting them are as described above.

Further, according to a specific example of the present invention, the thickness of the light emitting layer 50 is preferably 50 to 2,000 Å.

On the other hand, the electron transport layer 60 is deposited on the light emitting layer through a vacuum deposition method or a spin coating method.

Meanwhile, as the material of the electron transport layer 60 in the present invention, a known electron transport material that functions to stably transport electrons injected from the electron injection electrode (cathode) can be used. Examples of known electron transport materials include quinoline derivatives, in particular, tris (8-quinolinolate) aluminum (Alq ₃ ), Liq, TAZ, BAlq, beryllium bis (benzoquinoline-10-noate) (beryllium bis ( Materials such as benzoquinolin-10-olate: Bebq2), Compound 201, Compound 202, BCP, oxadiazole derivatives such as PBD, BMD, and BND may be used, but are not limited thereto.

TAZ BAlq

<Compound 201> <Compound 202> BCP

In addition, in the organic light emitting device of the present invention, after forming the electron transport layer, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be laminated on top of the electron transport layer. Not limiting.

Any material known as an electron injection layer formation material such as CsF, NaF, LiF, Li ₂ O, or BaO may be used as a material for forming the electron injection layer 70 . Deposition conditions for the electron injection layer vary depending on the compound used, but may generally be selected from a range of conditions almost identical to those for forming the hole injection layer.

The electron injection layer 70 may have a thickness of about 1 Å to about 100 Å or about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the aforementioned range, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.

In addition, in the present invention, the negative electrode 80 may use a material having a low work function to facilitate electron injection. Lithium (Li), magnesium (Mg), calcium (Ca), or alloys thereof aluminum (Al), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) etc., or a transmission type cathode using ITO or IZO may be used.

In addition, the organic light emitting device in the present invention may additionally include a light emitting layer of a blue light emitting material, a green light emitting material, or a red light emitting material emitting light in a wavelength range of 380 nm to 800 nm. That is, the light emitting layer in the present invention is a plurality of light emitting layers, and the blue light emitting material, green light emitting material, or red light emitting material in the light emitting layer additionally formed may be a fluorescent material or a phosphorescent material.

In addition, in the present invention, one or more layers selected from the respective layers may be formed by a single molecule deposition process or a solution process.

Here, the deposition process refers to a method of forming a thin film by evaporating a material used as a material for forming each layer through heating in a vacuum or low pressure state, and the solution process is to form each layer. It refers to a method of forming a thin film by mixing a material used as a material for a solvent with a solvent and mixing the same with a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, and the like.

In addition, the organic light emitting device in the present invention is a flat panel display device; flexible display devices; devices for monochromatic or white flat lighting; And monochromatic or white flexible lighting device; it can be used in any one device selected from.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for explaining the present invention in more detail, and it will be apparent to those skilled in the art that the scope of the present invention is not limited thereto.

Preparation Example 1. Synthesis of Compound 4

Synthesis of Intermediate 1-1

[Scheme 1-1]

[Intermediate 1-1]

7,7-dimethyl-7 H -benzo [ b ] fluoreno [3,4- d ] furan (150 g, 0.528 mol) and THF (1500 ml, 10 vol.) were put into a reactor, stirred, and cooled to minus 78 degrees. . After adding n-BuLi (363ml, 0.580mol) dropwise, the temperature was raised to room temperature and stirred overnight. After cooling to -78°C again, iodine (147.3g, 0.580mol) dissolved in THF (600ml, 4vol.) was added dropwise. The temperature was raised to room temperature and Na ₂ S ₂ O ₃ ag. was added to terminate the reaction. The reactants were extracted with EA/H ₂ O, the organic layers were collected and concentrated, filtered with methanol slurry, and dried to synthesize intermediate 1-1 (188 g, yield 86%).

Synthesis of Intermediates 1-2

[Scheme 1-2]

[Intermediate 1-1] [Intermediate 1-2]

Intermediate 1-1 (188g, 0.458mol) and methylene chloride (3008ml, 16vol.) were put into a reactor and stirred, and bromine (77g, 0.48mol) diluted in methylene chloride (376ml, 2vol.) was added dropwise. When the reaction was completed, an excess of methanol was added, methylene chloride was removed, filtered and dried to synthesize intermediate 1-2 (197 g, yield 88%) as a white solid.

Synthesis of intermediates 1-4

[Scheme 1-3]

[Intermediate 1-2] [Intermediate 1-3] [Intermediate 1-4]

Intermediate 1-2 (45 g, 0.092 mol), Intermediate 1-3 (55.4 g, 0.097 mol), Pd (pph ₃ ) ₄ (3.2 g, 0.003 mol), K ₂ CO ₃ (31.8 g, 0.230 mol) were added to the reactor. Into toluene (315ml), ethanol (180ml), H ₂ O (135ml) was added and stirred overnight at 75 degrees. After extraction with ethyl acetate/H ₂ O, the organic layer was concentrated and purified by column (methylene chloride/heptane) to synthesize Intermediate 1-4 (36.8 g, yield 49%).

Synthesis of compound 4

[Scheme 1-4]

[Intermediate 1-4] [Compound 4]

Intermediates 1-4 (13 g, 0.016 mol), phenylboronic acid (2.16 g, 0.018 mol), Pd (pph ₃ ) ₄ (0.56 g, 0.0004 mol), K ₂ CO ₃ (5.55 g, 0.040 mol) Into the reactor, toluene (91ml), ethanol (39ml), and H ₂ O (26ml) were added and stirred overnight at 75 degrees. After extracting with ethyl acetate/H ₂ O and concentrating the organic layer, the concentrated material was dissolved in toluene and hot filtered, and the filtrate was concentrated. Compound 4 (6g, yield 46%) was synthesized by recrystallization with methylene chloride and acetone.

Preparation Example 2. Synthesis of Compound 6

Synthesis of Intermediate 2-2

[Scheme 2-1]

[Intermediate 1-2] [Intermediate 2-1] [Intermediate 2-2]

Intermediate 2-2 (36.5 g, yield 52%) were synthesized.

Synthesis of compound 6

[Scheme 2-2]

[Intermediate 2-2] [Intermediate 2-3] [Compound 6]

Compound 6 (20 g, yield 55%) was synthesized in the same manner as in the synthesis of compound 4 using Intermediate 2-2 (36.5 g, 0.053 mol) and Intermediate 2-3 (12.4 g, 0.058 mol).

Preparation Example 3. Synthesis of Compound 7

Synthesis of Intermediate 3-1

[Scheme 3-1]

[Intermediate 3-1]

Synthesis of intermediate 1-2 using 7,7-dimethyl- 7H -benzo[ b ]fluoreno[3,4- d ]furan (130g, 0.457mol) and bromine (76.7g, 0.480mol) Intermediate 3-1 (156 g, yield 94%) was synthesized in the same manner.

Synthesis of Intermediate 3-2

[Scheme 3-2]

[Intermediate 3-1] [Intermediate 3-2]

Intermediate 3-2 (144 g, yield 93%) was prepared in the same manner as in the synthesis of Compound 4 using Compound 3-1 (156 g, 0.429 mol) and phenylboronic acid (47.6 g, 0.472 mol).

Synthesis of Intermediate 3-3

[Scheme 3-3]

[Intermediate 3-2] [Intermediate 3-3]

Compound 3-2 (14 g, 0.039 mol), n-BuLi (27 ml, 0.043 mol), and iodine (10.8 g, 0.043 mol) were used to synthesize Intermediate 3-3 (13 g, 0.043 mol) in the same manner as in the synthesis of Intermediate 1-1. Yield 68%) was prepared.

Synthesis of compound 7

[Scheme 3-4]

[Intermediate 3-3] [Compound 7]

Intermediate 3-3 (10 g, 0.02 mol) and N -phenyl-9-phenanthreneamine (6.1 g, 0.022 mol), Pd ₂ dba ₃ (0.37 g, 0.0004 mol), tributylphosphine (0.66 g, 0.0016 mol) ), sodium t-butoxide (3.9 g, 0.04 mol), and toluene (10 vol, 100 ml) were put into the reactor and stirred under reflux for 3 hours. After hot filtering in toluene, concentrating, and column purification, compound 7 (6g, yield 48%) was synthesized.

Preparation Example 4. Synthesis of Compound 2

Synthesis of intermediate 4-1

[Scheme 4-1]

[Intermediate 1-2] [Intermediate 4-1]

Intermediate 1-2 (15g, 0.03mol) synthesized in Preparation Example 1 and N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluorene-2 -Amine (12.3 g, 0.031 mol), Pd(OAc) 2 (0.3 g, 0.002 mol), Xanthene (0.9 g, 0.002 mol), STB (4.4 g, 0.046 mol), and toluene (150 ml) were put into a reactor and overnight It was stirred under reflux. After completion of the reaction, hot filter with toluene, concentration, and column purification to prepare intermediate 4-1 (12.5 g, yield 53%).

Synthesis of compound 2

[Scheme 4-2]

[Intermediate 4-1] [Compound 2]

Intermediate 4-1 (7.5g, 0.01mol) and phenylboronic acid (1.3g, 0.011mol), Pd (pph3)4 (0.3g, 0.0003mol), potassium carbonate (3.4g, 0.025mol), toluene ( 52ml), ethanol (30ml), and distilled water (22ml) were put into the reactor and stirred under reflux overnight. After extraction with ethyl acetate/distilled water, the organic layer was concentrated, and column purification was performed to obtain compound 2 (3 g, yield 40%).

Preparation Example 5. Synthesis of Compound 13

Synthesis of compound 13

[Scheme 5-1]

[Intermediate 4-1] [Compound 13]

Intermediate 4-1 (7.5g, 0.01mol) and 1-naphthylboronic acid (1.9g, 0.011mol), Pd (pph3)4 (0.3g, 0.0003mol), potassium carbonate (3.4g, 0.025mol), Toluene (52ml), ethanol (30ml), and distilled water (22ml) were added and stirred under reflux overnight. After extraction with ethyl acetate/distilled water and concentration of the organic layer, compound 13 (4g, yield 50%) was prepared by column purification.

Examples 1 to 11: Manufacturing of organic light emitting device

The ITO glass was patterned so that the light emitting area had a size of 2 mm × 2 mm, and then washed. After mounting the ITO glass in a vacuum chamber, the base pressure was set to 1 × 10 ^-7 torr, and then DNTPD (450 Å), [Formula G] (200 Å), and the present invention as a second hole transport layer material on the ITO The compounds (50 Å) shown in Tables 1 and 2 were formed into films. Subsequently, a film (200 Å) was formed by mixing [Formula BH]: [Formula BD] in a weight ratio (97: 3) on the light emitting layer, and then [Formula E-2] as an electron transport layer, 300 Å, and [Formula E-2] as an electron injection layer. 1] was formed in the order of 10 Å and Al (1000 Å) to prepare an organic light emitting device. The emission characteristics of the organic light emitting device were measured at 0.4 mA.

[DNTPD] [Formula G] [Formula E-1]

[Formula E-2] [Formula BH] [Formula BD]

Comparative Examples 1 and 2

In the device structure of the above embodiment, an organic light emitting device was manufactured in the same manner except for using the following formula B or formula C instead of the compound according to the present invention as the second hole transport layer compound, and the emission characteristics of the organic light emitting device were measured at 0.4 mA did

[Formula B] [Formula C]

With respect to the organic light emitting device manufactured according to Examples 1 to 9 and Comparative Example 1, driving voltage, efficiency and lifetime were measured, and the results are shown in [Table 1] below.

Driving voltage (V) Efficiency (Cd/A) Life (T97) Example 1 compound 1 3.40 7.8 98 Example 2 compound 3 3.49 7.7 42 Example 3 compound 4 3.42 7.6 48 Example 4 compound 5 3.44 7.6 85 Example 5 compound 6 3.43 7.3 109 Example 6 compound 7 3.46 7.4 31 Example 7 compound 26 3.49 7.4 32 Example 8 compound 31 3.47 7.4 34 Example 9 compound 24 3.45 7.3 125 Comparative Example 1 Formula B 3.46 6.9 20

As shown in Table 1, the organic light emitting device according to the present invention has high efficiency and excellent lifespan characteristics compared to the organic light emitting device using the compound of Comparative Example 1 according to the prior art, especially in the case of compounds 1, 6 and 24 It can be seen that the properties are much better.

In addition, with respect to the organic light emitting device manufactured according to Examples 10 to 11 and Comparative Example 2, driving voltage, efficiency, and external quantum efficiency (EQE) were measured, and the results are shown in [Table 2].

Driving voltage (V) Efficiency (Cd/A) EQE Example 10 compound 2 3.43 7.1 9.5 Example 11 compound 13 3.42 7.1 9.5 Comparative Example 2 formula C 3.43 6.6 8.9

As shown in Table 2, it can be seen that the organic light emitting device according to the present invention has higher efficiency compared to the organic light emitting device using the compound of Comparative Example 2 according to the prior art.

Claims (15)

A compound for an organic light emitting device represented by the following [Formula A] or [Formula B].
[Formula A]

[Formula B]
In [Formula A] and [Formula B],
The substituents X ₁ and X ₂ are each the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted Any one selected from cyclic aryl groups having 6 to 50 carbon atoms,
At least one of the substituents X ₁ and X ₂ is selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms which one,
The substituents R ₁ to R ₁₀ are each the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted Any one selected from aryl groups having 6 to 50 carbon atoms,
One of the substituents R ₃ to R ₁₀ is a substituent represented by the following structural formula A,
[Structural Formula A]

In the structural formula A,
The linking group L ₁ is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms,
Wherein k is an integer from 1 to 3, when k is 2 or more, each L ₁ is the same as or different from each other;
The substituents R ₁₁ and R ₁₂ are each the same or different, and each independently represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms,
The '*' is a binding site to an aromatic carbon atom bonded to any one of the substituents of R ₃ to R ₁₀ ;
'Substitution' in 'substituted or unsubstituted' in [Formula A] and [Formula B] is one or more substituents selected from the group consisting of heavy hydrogen, an alkyl group having 1 to 24 carbon atoms, and an aryl group having 6 to 24 carbon atoms. It means substituted, provided that the compound represented by P69 below is excluded.
According to claim 1,
The substituents R ₁ and R ₂ are each the same or different, and each independently represent any one selected from an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 18 carbon atoms.
According to claim 2,
Wherein the substituents R ₁ and R ₂ are each the same or different, and each independently represent any one substituent selected from methyl or phenyl.
According to claim 1,
One of the substituents X ₁ and X ₂ is selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms Any one of which is, and the other is a compound for an organic light emitting device, characterized in that hydrogen or deuterium.
According to claim 1,
At least one of the substituents X ₁ and X ₂ is selected from a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 18 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 18 carbon atoms A compound for an organic light emitting device, characterized in that any one of which is.
According to claim 5,
One of the substituents X ₁ and X ₂ is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and the other is a compound for an organic light emitting device, characterized in that hydrogen or deuterium.
delete According to claim 1,
The substituent R ₇ is a compound for an organic light emitting device, characterized in that a substituent represented by the following structural formula A.
[Structural Formula A]

Wherein R ₁₁ and R ₁₂ are each the same or different, and each independently represents a substituted or unsubstituted aryl group having 6 to 18 carbon atoms;
The L ₁ and k are as defined in claim 1.
[Formula 1] to [Formula 5], [Formula 7] to [Formula 11], [Formula 13] to [Formula 15], [Formula 18], [Formula 20] to [Formula 24], [Formula 26] to [Formula 41], [Formula 43], [Formula 45 to [Formula 52], [Formula 54] any one compound for an organic light emitting device selected from the group represented by.

[Compound 1] [Compound 2] [Compound 3]

[Compound 4] [Compound 5]

[Compound 7] [Compound 8] [Compound 9]

[Compound 10] [Compound 11]

[Compound 13] [Compound 14] [Compound 15]

[Compound 18]

[Compound 20] [Compound 21]

[Compound 22] [Compound 23] [Compound 24]

[Compound 26] [Compound 27]

[Compound 28] [Compound 29] [Compound 30]

[Compound 31] [Compound 32] [Compound 33]

[Compound 34] [Compound 35] [Compound 36]

[Compound 37] [Compound 38] [Compound 39]

[Compound 40] [Compound 41]

[Compound 43] [Compound 45]


[Compound 46] [Compound 47] [Compound 48]

[Compound 49] [Compound 50] [Compound 51]

[Compound 52] [Compound 54]
a first electrode;
a second electrode facing the first electrode; and
An organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one compound for an organic light emitting device according to any one of claims 1 to 6, 8 and 9. An organic light emitting device comprising:
According to claim 10,
The organic layer interposed between the first electrode and the second electrode in the organic light emitting device includes a hole transport layer or a hole injection layer, and the compound for the organic light emitting device is used for the hole transport layer or the hole injection layer. organic light-emitting device.
According to claim 11,
The hole transport layer includes a first hole transport layer using different materials and a second hole transport layer provided between the first hole transport layer and the light emitting layer,
The compound for an organic light emitting device is an organic light emitting device, characterized in that used in the second hole transport layer.
According to claim 11,
The organic layer further comprises at least one of a light emitting layer, a functional layer having a hole injection function and a hole transport function at the same time, an electron transport layer, and an electron injection layer.
According to claim 13,
At least one layer selected from the respective layers is an organic light emitting device, characterized in that formed by a deposition process or a solution process.
According to claim 10,
The organic light emitting diode may include a flat panel display device; flexible display devices; devices for monochromatic or white flat lighting; And, a monochromatic or white flexible lighting device; characterized in that used in any one device selected from the organic light emitting device.