KR102162247B1 - Antracene derivatives having heteroaryl substituted phenyl group and organic light-emitting diode including the same - Google Patents

Abstract

The present invention relates to an anthracene derivative represented by the following [Chemical Formula A] and an organic light-emitting device comprising the same. Substituents X ₁ to X ₅ , Y and Z are the same as defined by the bar described in the detailed description of the invention.
[Formula A]

Description

Anthracene derivatives having heteroaryl substituted phenyl group and organic light-emitting diode including the same.

The present invention relates to an anthracene derivative containing a phenyl group having a heteroaryl substituent and an organic light emitting device including the same, and in more detail, an anthracene derivative capable of lowering a driving voltage and showing excellent device characteristics with excellent luminous efficiency, and including the same It relates to an organic light emitting device.

Recently, as display devices have become larger, there is an increasing demand for flat display devices that occupy a small space. A liquid crystal display, a representative flat display device, has the advantage of being able to reduce weight compared to the existing CRT (cathode ray tube), but viewing angles (viewing angles). The angle) is limited and the back light is absolutely necessary. On the other hand, organic light emitting diodes (OLEDs), which are new flat display devices, are displays using a self-luminous phenomenon, and have advantages such as a large viewing angle, lightness and compactness compared to liquid crystal displays, and fast response speed. And, in recent years, applications to full-color displays or lighting are expected.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.

An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an 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 excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground. These organic light-emitting devices are 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 material layer in the organic light-emitting device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions. The light-emitting material may be classified into a high-molecular-type and a low-molecular-type according to its molecular weight, and may be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron according to the light emitting mechanism. . In addition, the light-emitting material may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary for realizing a better natural color according to the light-emitting color.

On the other hand, when only one material is used as a light-emitting material, the maximum emission wavelength shifts to a long wavelength due to intermolecular interactions, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect.Therefore, the increase in color purity and energy transfer A host-dopant system may be used as a light-emitting material in order to increase the luminous efficiency through.

The principle is that when a small amount of a dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

In order for the organic light-emitting device to fully exhibit the above-described excellent characteristics, materials that form the organic material layer in the device, such as a hole injection material, a hole transport material, a light-emitting material, an electron transport material, and an electron injection material, are supported by a stable and efficient material. It must be preceded.

On the other hand, in the organic light-emitting device, charges injected from both electrodes recombine in the light emitting layer to emit light, but since the moving speed of holes is faster than the moving speed of electrons, there is a problem that efficiency decreases due to some of the holes exiting the light emitting layer. Becomes. Therefore, there is a demand for an electron transport material having a high electron movement speed.

In order to manufacture an organic compound having excellent electron transport ability and hole blocking ability, excellent luminous efficiency, and high stability in a thin film state, Patent Publication No. 10-0691543 (2007.03.09) discloses four substitution places of anthracene. An organic compound into which one to two hetero functional groups are introduced is described, and in Unexamined Patent Publication No. 10-2012-0104204 (2012.09.20), an organic compound in which a pyridoindole derivative is bonded to a substituted anthracene ring structure is described. Has been described.

However, despite efforts to manufacture electron transport materials for organic light-emitting devices as described above, it is not yet sufficient to develop materials for low driving voltage or high luminous efficiency, so that light emission while driving at low voltage is possible. The necessity of developing a material for an electron transport layer for an organic light-emitting device having excellent efficiency is continuously required.

Registered Patent Publication No. 10-0691543 (2007.03.09)

Public Patent Publication No. 10-2012-0104204 (2012.09.20)

Accordingly, the first technical problem to be achieved by the present invention is to provide an organic compound for an organic light emitting device that can be used for an electron transport layer, has low voltage driving characteristics, and has excellent luminous efficiency.

A second technical problem to be achieved by the present invention is to provide an organic light-emitting device including the organic compound.

The present invention provides an anthracene derivative represented by the following [Formula A] as an organic compound that can be used in an electron transport layer of an organic light-emitting device in order to achieve the first technical problem.

[Formula A]

In the above [Formula A],

The Y is the same or different, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted carbon number of 1 to 50 A heteroaryl group, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms;

Z is the same or different, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted silyl having 1 to 30 carbon atoms It is any one selected from group;

m and m'are integers from 1 to 8;

When the substituents Y and Z are not bonded to carbon of the aromatic ring of the naphthyl group or anthracenyl group, hydrogen is bonded;

The X ₁ to X ₅ are each the same or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a 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 cycloalkenyl group having 5 to 30 carbon atoms, substituted or Unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C1-C30 alkylthioxy group, substituted or unsubstituted C5-C30 aryl Thioxy group, substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 50 carbon atoms, substituted or unsubstituted and heterogeneous It is any one selected from a C2-C50 heteroaryl group, a cyano group, a nitro group, and a halogen group having O, N or S as atoms, and forms a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero with adjacent groups Can;

At least one of X ₁ to X ₅ is a C 2 to C 20 heteroaryl group containing a nitrogen atom.

In addition, the present invention includes a first electrode, a second electrode opposite to the first electrode, and an organic layer interposed between the first electrode and the second electrode, and the organic layer is [ It provides an organic light-emitting device comprising at least one anthracene derivative represented by Formula A].

According to the present invention, an anthracene derivative represented by [Chemical Formula A] has characteristics of low voltage driving and excellent luminous efficiency compared to conventional materials, and thus can be used for manufacturing a stable and excellent device.

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

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

The present invention provides a compound represented by the following [Chemical Formula A] as an anthracene derivative that can be used in an electron transport layer or a light emitting layer of an organic light emitting device.

[Formula A]

In the above [Formula A],

The Y is the same or different, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted carbon number of 1 to 50 A heteroaryl group, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms;

Z is the same or different, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted silyl having 1 to 30 carbon atoms It is any one selected from group;

m and m'are integers from 1 to 8;

When the substituents Y and Z are not bonded to carbon of the aromatic ring of the naphthyl group or anthracenyl group, hydrogen is bonded;

The X ₁ to X ₅ are each the same or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a 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 cycloalkenyl group having 5 to 30 carbon atoms, substituted or Unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C1-C30 alkylthioxy group, substituted or unsubstituted C5-C30 aryl Thioxy group, substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 50 carbon atoms, substituted or unsubstituted and heterogeneous It is any one selected from a C2-C50 heteroaryl group, a cyano group, a nitro group, and a halogen group having O, N or S as atoms, and forms a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero with adjacent groups Can;

At least one of X ₁ to X ₅ is a C 2 to C 20 heteroaryl group containing a nitrogen atom;

'Substituted' in the'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 1 to 24 carbon atoms , C1-C24 alkynyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C6-C24 arylalkyl group, C2-C24 heteroaryl group, C2-C24 heteroarylalkyl group , C1-C24 alkoxy group, C1-C24 alkylamino group, C1-C24 arylamino group, C1-C24 hetero arylamino group, C1-C24 alkylsilyl group, C1-C24 arylsilyl It means substituted with one or more substituents selected from the group consisting of a group and an aryloxy group having 1 to 24 carbon atoms.

Meanwhile, the aryl group used in the compound of the present invention refers to an aromatic system consisting of a hydrocarbon including one or more rings, and when the substituent is present, it may be fused with neighboring substituents to further form a ring.

Specific examples of the aryl group include aromatic groups such as phenyl, naphthyl, tetrahydronaphthyl, and the like, and at least one hydrogen atom in the aryl group is a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group , Amino group (-NH ₂ , -NH(R), -N(R')(R''), R'and R" are independently of each other an alkyl group having 1 to 10 carbon atoms, 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, alkenyl group having 1 to 24 carbon atoms, alkynyl group having 1 to 24 carbon atoms , C1-C24 heteroalkyl group, C6-C24 aryl group, C6-C24 arylalkyl group, C2-C24 heteroaryl group, or C2-C24 heteroarylalkyl group.

The heteroaryl group as a substituent used in the compound of the present invention refers to a cyclic aromatic system having 2 to 24 carbon atoms including 1, 2 or 3 hetero atoms selected from N, O, P or S, and the remaining ring atoms are carbon, The rings may be fused to form a ring. And at least one hydrogen atom in the heteroaryl group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkyl group as a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, and the like, and at least one hydrogen atom in the alkyl group is The atom may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkoxy group that is a substituent used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group as a substituent used in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, methylcyclo Butylsilyl, dimethylfurylsilyl, and the like. At least one hydrogen atom in the silyl group may be substituted with the same substituent as in the case of the aryl group.

More specifically, Y and Z in [Chemical Formula A] of the present invention are each the same or different, and independently of each other, hydrogen, deuterium; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 5 to 20 carbon atoms; It is one selected from among, and m and m'may each be an integer of 1 to 4.

In this case, when at least one of the substituents X ₁ to X ₅ of [Formula A] is a heteroaryl group having 2 to 20 carbon atoms containing a nitrogen atom, the heteroaryl group is any one substituent selected from Structural Formulas 1 to 6 Can be

[Structural Formula 1]

[Structural Formula 2]

[Structural Formula 3]

[Structural Formula 4]

[Structural Formula 5]

[Structural Formula 6]

Here, T ₁ to T ₈ in Structural Formulas 1 to 6 are the same or different and independently of each other, C (R ₁₁ ), C (R ₁₁ ) (R ₁₂ ), N, N (R ₁₃ ), O, Is any one selected from S; Each of R1 to R13 is the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and a substituted or unsubstituted carbon number 3 Any one selected from a cycloalkyl group of to 30, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, each of the above In Structural Formulas 1 to 6, one of R1 to R13 is a single bond that forms a bond with the phenyl group in Formula A.

In the present invention, when at least one of the substituents X ₁ to X ₅ is a heteroaryl group having 2 to 20 carbon atoms including a nitrogen atom, the heteroaryl group may have a plurality of rings. Looking at the case where the heteroaryl group has a plurality of rings, it is divided into a ring of a heteroaryl portion containing nitrogen or a ring of a heteroaryl portion containing nitrogen and a ring of an aryl portion not containing a heteroatom. I can lose. In this case, the portion bonded to the phenyl group of Formula A may be a ring portion containing nitrogen or a ring of an aryl portion not containing nitrogen.

Looking at this through the substituent of the structural formula 3, in the case of the structural formula 3, if T ₁ to T ₃ have at least one nitrogen atom and T ₄ , T ₅ , R ₃ and R ₄ are an aryl group moiety that does not contain nitrogen The moiety bonded to the phenyl group of Formula A may be any one of T ₁ to T ₃ , or any one selected from T ₄ , T ₅ , R ₃ and R ₄ may be bonded to the phenyl group.

In this case, more preferably, the ring of the aryl group moiety that does not contain nitrogen may be a moiety bonded to the phenyl group of Formula A.

This can be similarly understood in [Structural Formula 4] to [Structural Formula 6].

Meanwhile, in the present invention, only one of the substituents X ₁ to X ₅ substituted with the phenyl group of Formula A may be any one of the substituents selected from Structural Formulas 1 to 6.

In the present invention, Structural Formulas 1 to 6 may each be a substituent containing 1 to 3 nitrogen atoms in the aromatic ring.

In addition, in the present invention, at least one of the substituents X ₁ to X ₅ of [Chemical Formula A] may be any one of the following substituents 101 to 606.

[Substituent 101] [Substituent 102] [Substituent 103]

[Substituent 104] [Substituent 105] [Substituent 106]

[Substituent 107] [Substituent 108] [Substituent 109]

[Substituent 110] [Substituent 111] [Substituent 112] [Substituent 113]

[Substituent 201] [Substituent 202] [Substituent 203]

[Substituent 204] [Substituent 205] [Substituent 206]

[Substituent 207] [Substituent 208]

[Substituent 301] [Substituent 302] [Substituent 303]

[Substituent 304] [Substituent 305] [Substituent 306]

[Substituent 307] [Substituent 308]

[Substituent 401] [Substituent 402] [Substituent 403]

[Substituent 404] [Substituent 405] [Substituent 406]

[Substituent 407] [Substituent 408] [Substituent 409]

[Substituent 410] [Substituent 411] [Substituent 412] [Substituent 413]

[Substituent 501] [Substituent 502] [Substituent 503]

[Substituent 601] [Substituent 602] [Substituent 603]

[Substituent 604] [Substituent 605] [Substituent 606]

Wherein R is the same or different and independently of each other, hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid or a salt thereof, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted C 1 To 60 alkoxy group, substituted or unsubstituted C1-C60 alkylthio group (alkylthio), substituted or unsubstituted C3-C60 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted Or an unsubstituted C5 to C60 aryloxy group, a substituted or unsubstituted C5 to C60 arylthio group, a substituted or unsubstituted C2 to C60 heteroaryl group, a substituted or unsubstituted C1 to C60 Of (alkyl) amino group, di(substituted or unsubstituted alkyl) amino group, or (substituted or unsubstituted aryl having 6 to 60 carbon atoms) amino group, di(substituted or unsubstituted C6 to C60) Aryl) amino group, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, and each substituent is adjacent to each other. Can be fused with groups to form a ring,

n is an integer from 0 to 9,

When the substituent R is not bonded to the carbon of the aromatic ring in the heteroaryl group of the substituents 101 to 606, hydrogen is bonded,

One of R is a single bond bonded to the phenyl group of [Formula A].

In this case, in the present invention, only one of the substituents X ₁ to X ₅ of [Formula A] may be any one of the substituents 101 to 606.

In addition, the present invention is 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 of the anthracene derivatives of the present invention.

In the present invention, "(organic layer) contains one or more organometallic compounds" means "(organic layer) one organometallic compound belonging to the scope of the present invention or two different kinds belonging to the organometallic compound It can be interpreted as "may include the above compounds.

In this case, the organic layer containing the compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, an emission layer, an electron transport layer, and an electron injection layer.

In addition, in the present invention, the organic layer interposed between the first electrode and the second electrode may include an electron transport layer and a light emitting layer.

In addition, in the present invention, the organic layer interposed between the first electrode and the second electrode may be an electron transport layer. In this case, the anthracene derivative of the present invention is included in the electron transport layer, and the emission layer may be formed of a host and a dopant. have.

In addition, in the present invention, specific examples of the dopant material used in the light emitting layer include pyrene-based compounds, deuterium-substituted pyrene-based compounds, fluorene-based compounds, deuterium-substituted fluorene-based compounds, benzofluorene-based compounds, deuterium-substituted Benzofluorene compounds, dibenzofluorene compounds, deuterium substituted dibenzofluorene compounds, indenophenanthrene compounds, deuterium substituted indenophenanthrene compounds, arylamines, deuterium substituted arylamines, peryl compounds , Deuterium substituted peryl compounds, pyrrole compounds, deuterium substituted pyrrole compounds, hydrazone compounds, deuterium substituted hydrazone compounds, carbazole compounds, deuterium substituted carbazole compounds, stilbene compounds, deuterium substituted stilbene compounds Compounds, starburst compounds, deuterium substituted starburst compounds, oxadiazole compounds, deuterium substituted oxadiazole compounds, coumarine, deuterium substituted coumarine, etc., but the present invention Is not limited by

In addition, as the host used in the light-emitting layer, Alq3, CBP (4,4'-N,N'-dicarbazole-biphenyl), PVK (poly(n-vinylcarbazole)), 9,10-di( Naphthalen-2-yl) anthracene (ADN), TCTA, TPBI (1,3,5-tris (N-phenylbenzimidazol-2-yl) benzene (1,3,5-tris (N-phenylbenzimidazole-2- yl)benzene)), TBADN (3-tert-butyl-9,10-di (naphth-2-yl) anthracene), E3, DSA (distyrylarylene), dmCBP (see formula below) and the host described above Deuterium substituents of the compounds may be used, but the present invention is not limited thereto.

PVK ADN

When the emission layer includes a host and a dopant, the content of the dopant may be generally 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.

Meanwhile, when the anthracene derivative is used in the electron transport layer in the present invention, the electron transport layer may be used by mixing other types of electron transport compounds in addition to the anthracene derivative of the present invention.

Herein, the compound for an electron transport layer different from the anthracene derivative may be a compound having a structure of Formula A as the anthracene derivative, but a compound of a different type, or an anthracene derivative not having the structure of Formula A, and the Non-anthracene-based compounds that do not have the structure of Formula A can be used as other types of compounds for electron transport layers.

As the compound for an electron transport layer not having the structure of Formula A, oxadiazole derivatives PBD, BMD, BND, Liq, Alq ₃ or a compound having the structure of Formula B may be used.

[Formula B]

In the above [Formula B],

Y is a portion in which any one selected from C, N, O, and S is directly bonded to the M to form a single bond, and a portion in which any one selected from C, N, O, and S forms a coordination bond to the M. It includes, and is a ligand chelated by the single bond and the coordination bond;

The M is an alkali metal, alkaline earth metal, aluminum (Al) or boron (B) atom, and the OA is a monovalent ligand capable of a single bond or coordination bond with the M,

O is oxygen,

A is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C2 to C20 An alkynyl group, 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 hetero atom having O, N or S as a hetero atom and having 2 to 50 carbon atoms Is any one selected from aryl groups,

When M is one metal selected from alkali metals, m = 1, n = 0,

When M is one metal selected from alkaline earth metals, m=1, n=1, or m=2, n=0,

When M is boron or aluminum, m is any one of 1 to 3, and n is any one of 0 to 2, satisfying m + n = 3.

More specifically, in the present invention, each of Y is the same or different, and may be any one selected from the following [Structural Formula C1] to [Structural Formula C39] independently of each other, but is not limited thereto.

[Structural Formula C1] [Structural Formula C2] [Structural Formula C3]

[Structural Formula C4] [Structural Formula C5] [Structural Formula C6]

[Structural Formula C7] [Structural Formula C8] [Structural Formula C9] [Structural Formula C10]

[Structural Formula C11] [Structural Formula C12] [Structural Formula C13]

[Structural Formula C14] [Structural Formula C15] [Structural Formula C16]

[Structural Formula C17] [Structural Formula C18] [Structural Formula C19] [Structural Formula C20]

[Structural Formula C21] [Structural Formula C22] [Structural Formula C23]

[Structural Formula C24] [Structural Formula C25] [Structural Formula C26]

[Structural Formula C27] [Structural Formula C28] [Structural Formula C29] [Structural Formula C30]

[Structural Formula C31] [Structural Formula C32] [Structural Formula C33]

[Structural Formula C34] [Structural Formula C35] [Structural Formula C36]

[Structural Formula C37] [Structural Formula C38] [Structural Formula C39]

In the [Structural Formula C1] to [Structural Formula C39],

R is the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted A heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or Unsubstituted C1-C30 alkylamino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted C6-C30 arylamino group, and substituted or unsubstituted C6-C30 arylsilyl It is any one selected from groups, and may be connected to an adjacent substituent with alkylene or alkenylene to form a spiro ring or a fused ring.

However, here, the'substitution' in the'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, hetero arylamino group, alkylsilyl group, aryl It means substituted with one or more substituents selected from the group consisting of silyl group, aryloxy group, aryl group, heteroaryl group, germanium, phosphorus and boron.

When the anthracene derivative in the present invention is mixed with other types of electron transporting compounds and used in the electron transport layer, the mixing ratio thereof may be 10:90 to 90:10 as weight %, preferably 25:75 to 75: May be 25.

Meanwhile, in the present invention, at least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer may be formed by a single molecule deposition method or a solution process, and the The organic light-emitting device may be used for a display device, a display device, or a single color or white lighting device.

Hereinafter, the organic light-emitting device of the present invention will be described with reference to FIG. 1.

1 is a cross-sectional view showing the structure of an organic light-emitting device of the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60, and a cathode 80, and if necessary, a hole injection layer 30 and an electron The injection layer 70 may be further included, and in addition, one or two intermediate layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, an organic light-emitting device of the present invention and a method of manufacturing the same are as follows. First, an anode 20 is formed by coating a material for an anode electrode on the substrate 10. Here, as the substrate 10, a substrate used in a conventional organic EL device is used, and an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling and waterproofness is preferable. In addition, as a material 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 evaporation or spin coating on the anode 20 electrode. Then, the hole transport layer material is vacuum thermally evaporated or spin coated on the hole injection layer 30 to form the hole transport layer 40.

Subsequently, an organic light-emitting layer 50 is stacked on the hole transport layer 40, and a hole blocking layer (not shown) is selectively formed on the organic light-emitting layer 50 by vacuum deposition or spin coating to form a thin film. can do. The hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level because when holes pass through the organic light emitting layer and flow into the cathode, the life and efficiency of the device are reduced. . In this case, the hole blocking material to be used is not particularly limited, but must have an electron transport ability and an ionization potential higher than that of the light emitting compound, and representatively, BAlq, BCP, TPBI, etc. may be used.

After depositing the electron transport layer 60 on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode-forming metal is vacuum-heated on the electron injection layer 70. The organic EL device is completed by vapor deposition to form the cathode 80 electrode. Here, the cathode-forming metal is lithium (Li), magnesium (Mg), aluminum (Al), aluminum-ridium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver ( Mg-Ag) or the like may be used, and in order to obtain a top light emitting device, a transmissive cathode using ITO or IZO may be used.

In addition, the emission layer may be formed of a host and a dopant.

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

In this case, the dopant used in the light emitting layer may be a compound represented by the following [Chemical Formula 1] or [Chemical Formula 2].

[Formula 1] [Formula 2]

In [Chemical Formula 1] and [Chemical Formula 2],

A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms , Substituted or unsubstituted and is any one selected from a heteroarylene group having 3 to 50 carbon atoms having O, N or S as a hetero atom, preferably anthracene, pyrene, phenanthrene, indenophenanthrene, chrysene, naphtha These are sen, picene, triphenylene, perylene, and pentacene.

In this case, A may be a compound represented by the following Formulas A1 to A10.

[Formula A1] [Formula A2] [Formula A3]

[Formula A4] [Formula A5] Formula A6]

[Formula A7] [Formula A8] [Formula A9]

[Formula A10]

Wherein Z ₁ to Z ₂ in the [Chemical Formula A3] are hydrogen, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number 2 To 60 alkynyl group, substituted or unsubstituted C1-C60 alkoxy group, substituted or unsubstituted C1-C60 alkylthio group (alkylthio), substituted or unsubstituted C3-C60 cycloalkyl group, substituted Or an unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C5 to C60 aryloxy group, a substituted or unsubstituted C5 to C60 arylthio group, a substituted or unsubstituted C2 to C60 Heteroaryl group, substituted or unsubstituted (alkyl) amino group having 1 to 60 carbon atoms, di(substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or (substituted or unsubstituted aryl having 6 to 60 carbon atoms) amino group , At least one selected from the group consisting of a di (substituted or unsubstituted aryl having 6 to 60 carbon atoms) amino group, and each of Z ₁ to Z ₂ is the same or different from each other, and may form a condensed ring with a group adjacent to each other. .

In addition, in [Chemical Formula 1],

The X ₁ and X ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, and X ₁ and X ₂ may be bonded to each other,

The Y ₁ and Y ₂ are each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted Or an unsubstituted C1-C24 heteroalkyl group, a substituted or unsubstituted C3-C24 cycloalkyl group, a substituted or unsubstituted C1-C24 alkoxy group, a cyano group, a halogen group, a substituted or unsubstituted carbon number 1 from the group consisting of 6 to 24 aryloxy groups, substituted or unsubstituted alkylsilyl groups having 1 to 40 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium and hydrogen More than one species is selected, and each of Y ₁ to Y ₂ is the same or different from each other, and may form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero with a group adjacent to each other.

Each of l and m is an integer of 1 to 20, and n is an integer of 1 to 4.

In addition, in [Chemical Formula 2],

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, but when b is 2 or more, each cycloalkane may be in a fused form, and the hydrogen substituted thereto Each may be substituted with deuterium or alkyl, and may be the same as or different from each other. .

The B is a single bond or -[C(R ₅ )(R ₆ )] _p -, and p is an integer of 1 to 3, but when p is 2 or more, two or more R ₅ and R ₆ are the same or different from each other ;

The R ₁ , R ₂ , R _{3 ,} R ₅ and R ₆ are independently of each other, hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group, or A salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms , A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number 6 to 60 aryl group, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, substituted Or an unsubstituted C1-C60 alkyl amino group, a di(substituted or unsubstituted C1-C60 alkyl) amino group, or a (substituted or unsubstituted C6-C60 aryl) amino group, a di(substituted or unsubstituted Aryl) amino group having 6 to 60 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms,

a is an integer of 1 to 4, but when a is 2 or more, 2 or more R ₃ are the same as or different from each other, and when R ₃ is plural, each R ₃ may be a fused form, and n is 1 to 4 It is an integer.

In addition, the amine group bonded to A of [Formula 1] and [Formula 2] may be represented by any one selected from the group represented by the following [Substituent 1] to [Substituent 52], but is not limited thereto.

[Substituent 1] [Substituent 2] [Substituent 3]

[Substituent 4] [Substituent 5] [Substituent 6]

[Substituent 7] [Substituent 8] [Substituent 9]

[Substituent 10] [Substituent 11] [Substituent 12]

[Substituent 13] [Substituent 14] [Substituent 15]

[Substituent 16] [Substituent 17] [Substituent 18]

[Substituent 19] [Substituent 20] [Substituent 21]

[Substituent 22] [Substituent 23] [Substituent 24]

[Substituent 25] [Substituent 26] [Substituent 27]

[Substituent 28] [Substituent 29] [Substituent 30]

[Substituent 31] [Substituent 32] [Substituent 33]

[Substituent 34] [Substituent 35] [Substituent 36]

[Substituent 37] [Substituent 38] [Substituent 39]

[Substituent 40] [Substituent 41] [Substituent 42]

[Substituent 43] [Substituent 44] [Substituent 45]

[Substituent 46] [Substituent 47] [Substituent 48]

[Substituent 49] [Substituent 50] [Substituent 51]

[Substituent 52]

In the above substituents, R is the same or different, and independently of each other, hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or its Salt, phosphoric acid or a salt thereof, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted An alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms , A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number 1 (Alkyl) amino group of to 60, di(substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or (substituted or unsubstituted aryl of 6 to 60 carbon atoms) amino group, di(substituted or unsubstituted 6 to carbon number) 60 aryl) amino group, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, may be selected from boron, each 1 to 12 Up to may be substituted, and each of the substituents may form a condensed ring with a group adjacent to each other.

In addition, in the present invention, the host may be a compound represented by the following Formulas 1A to 1D.

[Formula 1A]

In Formula 1A,

The Ar _{7 ,} Ar ₈ and Ar ₉ are the same as or different from each other, and each independently, a single bond, a substituted or unsubstituted C ₅ -C ₆₀ aromatic linking group, or a substituted or unsubstituted C ₂ -C ₆₀ heteroaromatic linking group;

The R ₂₁ to R ₃₀ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or A salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group (alkylthio), a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl Group, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted carbon number 1 to 60 (alkyl) amino group, di(substituted or unsubstituted C 1 to C 60 alkyl) amino group, or (substituted or unsubstituted C 6 to C 60 aryl) amino group, di(substituted or unsubstituted C 6 To 60 aryl) amino group, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, and each substituent is May form a condensed ring with groups adjacent to each other;

E, f, and g are the same as or different from each other, and are each independently an integer of 0 or 1 to 4;

The two sites marked with * of the anthracene may be the same or different from each other, and each independently combine with the P or Q structure to form an anthracene derivative selected from Formulas 1Aa-1 to 1Aa-3 below.

[Formula 1Aa-1] [Formula 1Aa-2] [Formula 1Aa-3]

Here, the'substituted' in the'substituted or unsubstituted' is deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, and Alkenyl group, alkynyl group having 1 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, or heteroaryl having 2 to 24 carbon atoms Arylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C1-C24 arylamino group, C1-C24 hetero arylamino group, C1-C24 alkylsilyl group, C1-C24 It means substituted with at least one substituent selected from the group consisting of an arylsilyl group and an aryloxy group having 1 to 24 carbon atoms.

[Formula 1B]

In Formula 1B,

The Ar ₁₇ to Ar ₂₀ are the same as or different from each other and each independently consists of the same substituent as defined in Ar ₇ to Ar ₈ in Formula 1A, and R ₆₀ to R ₆₃ are defined in R ₂₁ to R ₃₀ of Formula 1A. It consists of the same substituents as.

The w and ww are the same as or different from each other, the x and xx are the same as or different from each other, and the w+ww and x+xx values are the same or different from each other, and are each independently an integer of 0 to 3. Further, y and yy are the same as or different from each other, z and zz are the same or different from each other, y+yy to z+zz values are 2 or less, and are integers of 0 to 2, respectively.

[Formula 1C]

In Formula 1C,

The Ar ₂₁ to Ar ₂₄ are the same as or different from each other and each independently consists of the same substituents as defined in Ar ₇ to Ar ₈ of Formula 1A, and R ₆₄ to R ₆₇ are in R ₂₁ to R ₃₀ of Formula 1A. It consists of the same substituents as defined.

In addition, ee to hh are the same as or different from each other, and each independently an integer of 1 to 4, and ii to ll are the same or different from each other, and each independently an integer of 0 to 4.

[Formula 1D]

In Formula 1D,

The Ar ₂₅ to Ar ₂₇ are the same as or different from each other and each independently consists of the same substituents as defined in Ar ₇ to Ar ₈ of Formula 1A, and R ₆₈ to R ₇₃ are the same as or different from each other, and each independently of the above formula It consists of the same substituents as defined for R ₂₁ to R ₃₀ in 1A, and each of the substituents may form a saturated or unsaturated cyclic structure between adjacent ones. In addition, the mm to ss are the same as or different from each other, and each independently an integer of 0 to 4.

More specifically, the host may be represented by any one selected from the group represented by the following [Compound 1] to [Compound 56], but is not limited thereto.

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

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

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

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

[화합물13] [화합물14] [화합물15]

[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]

[Compound 55] [Compound 56]

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

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 of ordinary skill in the art that the scope of the present invention is not limited thereto.

<Example>

Synthesis Example 1. Synthesis of [Compound 1]

Synthesis Example 1-1) Synthesis of (10-(naphthalen-1-yl) anthracene-9-yl) boronic acid

Synthesis Example 1-1-a) Synthesis of 9-(naphthalen-1-yl)anthracene

In a round bottom flask, 1-naphthalene boronic acid 27.2 g (158 mmol), 9-bromoanthracene 34 g (132 mmol), potassium carbonate 36.6 g (264 mmol), Pd (PPh ₃ ) ₄ 3 g (2 mmol), 70 ml of water, 180 ml of toluene and 180 ml of tetrahydrofuran was added and subjected to reflux reaction.

After the reaction was completed, the layers were separated, the aqueous layer was removed, and the organic layer was concentrated under reduced pressure, and 27.2 g (yield 81%) of 9-(naphthalen-1-yl)anthracene was obtained by column chromatography.

Synthesis Example 1-1-b) Synthesis of 9-bromo-10-(naphthalen-1-yl)anthracene

In a round-bottom flask, 9-(naphthalen-1-yl)anthracene 27.2g (0.108mol) prepared in Synthesis Example 1-1-a) and 250ml of dichloromethane were added to dissolve the crystals at room temperature, and then cooled to 0°C. Thereafter, 17.2 g (0.107 mol) of bromine was diluted in 50 ml of dichloromethane and slowly added thereto to react. After completion of the reaction, the layers were separated, the aqueous layer was removed, the organic layer was concentrated under reduced pressure, and crystals were precipitated with methanol, and then recrystallized to 26 g of yellow 9-bromo-10-(naphthalen-1-yl)anthracene crystals (yield 76%). Got

Synthesis Example 1-1-c) Synthesis of (10-naphthalen-1-yl) anthracene-9-yl) boronic acid

In a round-bottom flask, 9-bromo-10-(naphthalen-1-yl)anthracene (26 g, 68 mmol) prepared in Synthesis Example 1-1-b was dissolved in 210 mL of THF. While cooled to -78 °C, n-butyllithium (51 mL) was slowly added. After the addition was completed, trimethyl borate (33.1 g, 95 mmol) was added after stirring at -78 °C for about 1 hour. After stirring for 1 hour at -78°C, the mixture was stirred at room temperature for about 2 hours, and 2N aqueous hydrochloric acid was added to adjust acidity. After extraction with EA, crystals were obtained with hexane while removing the solvent to obtain 18 g of (10-naphthalen-1-yl) anthracene-9-yl) boronic acid (yield 76.2%).

Synthesis Example 1-2) Synthesis of 1-(4-bromophenyl)-1H-1,2,4-triazole

In a round bottom flask, 1-bromo-4-iodobenzene 37.3 g (132 mmol), (1H-1,2,4-triazol-1-yl) boronic acid 14.2 g (125 mmol), potassium carbonate 36.6 g (264 mmol) ), Pd (PPh ₃ ) ₄ 3 g (2 mmol), 70 ml of water, 180 ml of toluene and 180 ml of tetrahydrofuran were added and subjected to reflux reaction.

After completion of the reaction, the layers were separated, the aqueous layer was removed, and the organic layer was concentrated under reduced pressure, and 1-(4-bromophenyl)-1H-1,2,4-triazole 21.5 g (yield 77%) using column chromatography. ).

Synthesis Example 1-3) Synthesis of [Compound 1]

Instead of 9-bromoanthracene used in Synthesis Example 1-1-a, 1-(4-bromophenyl)-1H-1,2,4-triazole prepared in Synthesis Example 1-2 was used, 1- [Compound 1] was synthesized using the same method except that (10-naphthalen-1-yl) anthracene-9-yl) boronic acid prepared in Synthesis Example 1-1 was used instead of naphthalene boronic acid. (4.3g, yield 52%)

MS (MALDI-TOF): m/z 447 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ:

119.6,125.4,125.6,126.3,127.2,127.9,128.3,129,130.1,130.9,131.8,133.1,133.6,134.2,134.7,137.2,143.3,153.6 [32C]

Synthesis Example 2. Synthesis of [Compound 2]

Synthesis Example 2-1) Synthesis of 6-(3-bromophenyl)quinoxaline

Using 1-bromo-3-iodobenzene instead of 1-bromo-4-iodobenzene used in Synthesis Example 1-2, (1H-1,2,4-triazol-1-yl) 6-(3-bromophenyl)quinoxaline was obtained using the same method, except that 6-quinoxaline boronic acid was used instead of boronic acid. (22g, yield 75%)

Synthesis Example 2-2) Synthesis of [Compound 2]

Instead of 1-(4-bromophenyl)-1H-1,2,4-triazole used in Synthesis Example 1-3, 6-(3-bromophenyl)quinoxaline prepared in Synthesis Example 2-1 [Compound 2] was synthesized using the same method except for using. (4.0 g, yield 50%)

MS (MALDI-TOF): m/z 509 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ:

119.6,125.3,125.4,125.6,126.2,126.3,126.8,127.1,127.2,127.9,128.3,129,129.7,130.9,131.8,133.1,134.2,137,137.2,140.8,141.1,142.7,144.8 [38C]

Synthesis Example 3. Synthesis of [Compound 3]

Synthesis Example 3-1) Synthesis of 2-(4-bromophenyl)pyrimidine

Using the same method, except that 2-pyrimidylboronic acid was used instead of the (1H-1,2,4-triazol-1-yl) boronic acid used in Synthesis Example 1-2, 2-(4- Bromophenyl) pyrimidine was obtained (20 g, yield 76%).

Synthesis Example 3-2) Synthesis of [Compound 3]

2-(4-bromophenyl)pyrimidine prepared in Synthesis Example 3-1 instead of 1-(4-bromophenyl)-1H-1,2,4-triazole used in Synthesis Example 1-3 [Compound 3] was synthesized using the same method except for using. (3.9 g, yield 48%)

MS (MALDI-TOF): m/z 459 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ:

117.7,119.6,125.4,125.6,126.3,127.2,128,128.3,129,130.9,131.8,133.1,133.6,134.2,137.2,156.1,164.2 [34C]

Synthesis Example 4. Synthesis of [Compound 4]

Synthesis Example 4-1) Synthesis of 2-(4-bromophenyl)-1,8-naphthyridine

The same method except that (1,8-naphthyridin-2-yl) boronic acid was used instead of (1H-1,2,4-triazol-1-yl) boronic acid used in Synthesis Example 1-2. To obtain 2-(4-bromophenyl)-1,8-naphthyridine (21 g, yield 77%).

Synthesis Example 4-2) Synthesis of [Compound 4]

2-(4-bromophenyl)-1 prepared in Synthesis Example 4-1 instead of 1-(4-bromophenyl)-1H-1,2,4-triazole used in Synthesis Example 1-3 [Compound 4] was synthesized using the same method except that, 8-naphthyridine was used. (3.5g, yield 47%)

MS (MALDI-TOF): m/z 509 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ:

117.1,119.6,120.9,121.7,125.4,125.6,126.3,127.2,128.1,128.3,129,130.9,131.8,132.2,133.1,134.2,135.2,137.2,137.9,138.4,153,154.6,156.2 [38C]

Synthesis Example 5. Synthesis of [Compound 5]

Synthesis Example 5-1) Synthesis of 2-methyl-2H-1,2,3-benzotriazole-5-boronic acid

Scheme 5-1)

In a round bottom flask, 5-bromo-2-methyl-2H-1,2,3-benzotriazole (8.5 g, 40 mmol) was dissolved in 650 mL of THF. After cooling to -78 °C, n-BuLi (30 mL) was slowly added. After the addition was completed, trimethyl borate (5.9 g, 56 mmol) was added after stirring at -78 °C for about 1 hour. After stirring at -78 °C for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2 N HCl was added to adjust the acidity. After extraction with EA, while removing the solvent, crystals were obtained with hexane to obtain a product. (5.5g, yield 78%)

Synthesis Example 5-2) Synthesis of 5-(3-bromophenyl)-2-methyl-2H-benzo[d][1,2,3]triazole

Instead of 6-quinoxalin boronic acid used in Synthesis Example 2-1), 2-methyl-2H-1,2,3-benzotriazole-5-boronic acid prepared in Synthesis Example 5-1) was used. Except that, 5-(3-bromophenyl)-2-methyl-2H-benzo[d][1,2,3]triazole was obtained using the same method. (21g, yield 70%)

Synthesis Example 5-3) Synthesis of [Compound 5]

Instead of 6-(3-bromophenyl)quinoxaline used in Synthesis Example 2-2, 5-(3-bromophenyl)-2-methyl-2H-benzo[d] prepared in Synthesis Example 5-2 [Compound 5] was synthesized using the same method except that [1,2,3]triazole was used. (4.2 g, yield 52%)

MS (MALDI-TOF): m/z 512 [M] ⁺ . ¹³ CNMR(75MHz, CDCl ₃ )δ: 43.9,119.6,125.1,125.4,125.6,127.4,127.6,127.9,129,129.2,130,130.1,130.9,131.8,131.9,133.1,135.4,136.5,136.7,137.2,138.4,144.3, 145.5 [37C]

Synthesis Example 6. Synthesis of [Compound 6]

Synthesis Example 6-1. Synthesis of 2,6-dialkyl substituted 10-(naphthalen-1-yl)anthracene-9-yl boronic acid

Synthesis Example 6-1-a) Synthesis of 2,6-dialkyl-substituted anthracene derivatives

2-Methyl-2-hexanol (35 g, 300 mmol) and anthracene (18.4 g, 100 mmol) were added to 50 mL trifluoroacetic acid and refluxed for 24 hours under nitrogen. Upon completion of the reaction, the mixture was cooled to room temperature and extracted with dichloromethane. The resulting solid was filtered while the organic layer was concentrated under reduced pressure, and then separated by column chromatography. The product was obtained by recrystallization from methanol. (6g, yield 16%) was obtained.

Synthesis Example 6-1-b) Synthesis of 2,6-dialkyl-substituted 9,10-dibromoanthracene

The 2,6-dialkyl-substituted anthracene (6g, 16mmol) synthesized in Synthesis Example 6-1-a was added to 100mL dichloroethane, and bromine (2.1mL, 40mmol) was added dropwise while stirring at room temperature for 4 hours. This was poured into water and sodium sulfate was added to consume residual bromine. Subsequently, this was extracted with dichloromethane, and the organic layer was dried over magnesium sulfate. The resulting material was passed through an alumina column using a dichloromethane eluent, and then evaporated, and methanol was added to precipitate a pale yellow solid to obtain about 7.2 g of the product.

Synthesis Example 6-1-c) Synthesis of 2,6-dialkyl-substituted 9-bromo-10-naphthalen-1-yl anthracene

In a round-bottom flask, the 2,6-dialkyl-substituted 9,10-dibromoanthracene prepared in Synthesis Example 6-1-b 7.2 g (13 mmol), 1-naphthalene boronic acid 2.4 g (13 mmol), potassium carbonate 3.7 g (27 mmol), Pd (PPh ₃ ) ₄ 0.3 g ( ₃ mmol), 15 ml of water, 40 ml of toluene and 40 ml of tetrahydrofuran were added and subjected to reflux reaction.

After completion of the reaction, the layers were separated, the aqueous layer was removed, the organic layer was concentrated under reduced pressure, and recrystallized from toluene hexane to obtain a product. (5.5g, yield 76%) was obtained.

Synthesis Example 6-1-d) Synthesis of 2-(naphthalen-1-yl) anthracene-9-yl boronic acid substituted with 2,6-dialkyl

2,6-dialkyl substituted 9-bromo prepared in Synthesis Example 6-1-c) instead of 9-bromo-10-(naphthalen-1-yl)anthracene used in Synthesis Example 1-1-c Boronic acid was synthesized using the same method except that -10-naphthalen-1-yl anthracene was used.

Synthesis Example 6-2) Synthesis of 5-(3-bromophenyl)-1,10-phenanthroline

5-(3-bromo) using the same method, except that (1,10-phenanthroline-5-yl) boronic acid was used instead of 6-quinoxaline boronic acid used in Synthesis Example 2-1). Phenyl)-1,10-phenanthroline was obtained (18 g, yield 67%).

Synthesis Example 6-3) Synthesis of [Compound 6]

Instead of 6-(3-bromophenyl)quinoxaline used in Synthesis Example 2-2, 5-(3-bromophenyl)-1,10-phenanthroline prepared in Synthesis Example 6-2 was used, and , (10-naphthalen-1-yl) anthracene-9-yl boronic acid substituted with 2,6-dialkyl-substituted 10-(naphthalen-1-yl) anthracene-9-yl boron prepared in Synthesis Example 6-1 [Compound 6] was synthesized using the same method except that an acid was used. (4.5g, yield 50%)

MS (MALDI-TOF): m/z 755 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ:

14.1,23.3,26.4,29.1,38,44.4,119.6,120.1,121.5,122.3,123.5,124.7,125.4,126.2,126.3,126.8,127.2,128.3,128.4,129.7,130.3,131,131.6,131.8,132.9,133.1, 134.2,135.7,136.4 ,136.6,137,147.3,149.9,154.6 [56C]

Synthesis Example 7. Synthesis of [Compound 7]

Synthesis Example 7-1) Synthesis of 1-benzyl-5-bromo-2-phenyl-1H-benzimidazole

A solution of 4-methylbenzenesulfonic acid (3.1 g, 16 mmol) in N ¹ -benzyl-4-bromobenzene-1,2-diamine (45 g, 160 mmol), dichloromethane 500 mL, and trimethylorthobenzoate 30 mL And reacted for about 40 hours at room temperature under nitrogen. After completion of the reaction, the organic layer was concentrated under reduced pressure, washed with 40% methanol/water and sodium hydrogencarbonate/water, and dried to obtain a product (22.3g, yield 40%).

Synthesis Example 7-2) Synthesis of (1,2-diphenyl-1H-benzo[d]imidazol-5-yl)boronic acid

1-benzyl-5-bromo-2-phenyl- prepared in Synthesis Example 7-1) instead of 9-bromo-10-(naphthalen-1-yl)anthracene used in Synthesis Example 1-1-c) The product was obtained using the same method except that 1H-benzimidazole was used (7 g, 35% yield).

Synthesis Example 7-3) Synthesis of 5-(4-bromophenyl)-1,2-diphenyl-1H-benzo[d]imidazole

Instead of (1H-1,2,4-triazol-1-yl) boronic acid used in Synthesis Example 1-2), (1,2-diphenyl-1H-benzo[ A product was obtained in the same manner except that d]imidazol-5-yl)boronic acid was used. (6.5g, yield 80%)

Synthesis Example 7-4) Synthesis of [Compound 7]

5-(4-bromophenyl)- prepared in Synthesis Example 7-3) instead of 1-(4-bromophenyl)-1H-1,2,4-triazole used in Synthesis Example 1-3) [Compound 7] was synthesized using the same method, except that 1,2-diphenyl-1H-benzo[d]imidazole was used. (4.0 g, yield 53%)

MS (MALDI-TOF): m/z 649 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ:

114.6,115.7,119.6,122.1,122.9,125.4,125.6,126.3,127.2,127.5,128.2,128.3,129,129.2,129.6,130.9,131,131.1,131.8,132.5,133.1,134,134.2,137.2,138.2,139.4,139.7,143.2, 149.4 [49C]

Synthesis Example 8. Synthesis of [Compound 8]

Synthesis Example 8-1) Synthesis of 2-(3,5-dibromophenyl)-1,3,4-oxadiazole

Scheme 8-1)

1,3-dibromo-5-iodobenzene was used instead of 1-bromo-4-iodobenzene used in Synthesis Example 1-2), and (1H-1,2,4-triazole-1 The product was obtained using the same method except that (1,3,4-oxadiazol-2-yl) boronic acid was used instead of -yl) boronic acid. (31.3 g, yield 71%)

Synthesis Example 8-2) Synthesis of 2-(5-bromo-[1,1'-biphenyl]-3-yl)-1,3,4-oxadiazole

Scheme 8-2)

2-(3,5-dibromophenyl)-1,3,4-oxadia prepared in Synthesis Example 8-1) instead of 1-bromo-4-iodobenzene used in Synthesis Example 8-1) A product was obtained using the same method, except that a sol was used and phenylboronic acid was used instead of (1,3,4-oxadiazol-2-yl)boronic acid. (25g, yield 72%)

Synthesis Example 8-3) Synthesis of [Compound 8]

2-(5-bromo-[ prepared in Synthesis Example 8-2) instead of 1-(4-bromophenyl)-1H-1,2,4-triazole used in Synthesis Example 1-3) [Compound 8] was synthesized using the same method except that 1,1'-biphenyl]-3-yl)-1,3,4-oxadiazole was used. (4.0 g, yield 47%)

MS (MALDI-TOF): m/z 525 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ:

119.6,124.7,125.4,125.6,126.2,126.3,127.1,127.2,127.6,127.9,128.3,129,129.2,130.9,131.8,133.1,134.2,137.2,137.5,140.8,153.3,164.5 [38C]

Synthesis Example 9. Synthesis of [Compound 9]

Synthesis Example 9-1) Synthesis of 2,2'-(5-bromo-1,3-phenylene)bis(1,3,4-oxadiazole)

Scheme 9-1)

Instead of 1,3-dibromo-5-iodobenzene used in Synthesis Example 8-1), 1-bromo-3,5-diiodobenzene was used, and (1,3,4-oxadiazole- A product was obtained using the same method, except that 1.95 equivalents of 2-day) boronic acid were used. (18g, 72% yield)

Synthesis Example 9-2) Synthesis of [Compound 9]

Synthesis Example 9-1 instead of 2-(5-bromo-[1,1'-biphenyl]-3-yl)-1,3,4-oxadiazole used in Synthesis Example 8-3) [Compound 9] was synthesized using the same method except that 2,2'-(5-bromo-1,3-phenylene)bis(1,3,4-oxadiazole) prepared in was used. I did. (4.2 g, yield 46%)

MS (MALDI-TOF): m/z 517 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ:

119.6,124.3,125.4,125.6,125.8,126.3,127.1,127.2,128.3,129,130.9,131.8,133.1,134.2,137.2,137.5,153.3,164.5 [34C]

Examples 1 to 9

Fabrication of organic light emitting device

The ITO glass was patterned so that the light emitting area was 2 mm × 2 mm in size and washed. After mounting the substrate in the vacuum chamber, the base pressure is 1×10 ^-7 torr, and then the organic material is placed on the ITO with DNTPD (700 Å), NPD (300 Å), [Formula 4] (95wt%) + [Formula 5] ](5 wt%) (250 Å), selected from [Compound 1] to [Compound 9] prepared by the present invention and sequentially formed (300 Å), then LiF (10 Å), Al (1,000 Å) The film was formed in the order of and was measured at 0.4 mA.

The structures of [Chemical Formula 4] and [Chemical Formula 5] and [Compound 1] to [Compound 9] are as follows.

[Formula 4] [Formula 5]

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

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

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

[Liq]

Example 10

Prepared in the same manner as in Example 3, except that [Compound 3] prepared by the present invention in the electron transport layer and the Liq (Lithium 8-hydroxy quinolate) corresponding to the conventional electron transport layer material in a weight% ratio of 50: It was mixed and used at 50.

Example 11

It was prepared in the same manner as in Example 3, except that [Chemical Formula 6] was used instead of [Chemical Formula 5] used in the light emitting layer.

[Chemical Formula 6]

Example 12

It was prepared in the same manner as in Example 3, except that [Chemical Formula 7] was used instead of [Chemical Formula 5] used in the light emitting layer.

[Chemical Formula 7]

Comparative example

The organic light emitting device for the comparative example was fabricated in the same manner as in the device structures of Examples 1 to 9 except that Alq ₃ was used instead of the compound prepared by the present invention in the electron transport layer.

[Alq ₃ ]

As shown in [Table 1], in the case of the organic electroluminescent device including the anthracene derivative compound according to the present invention in the electron transport layer, the improved electron transport ability compared to the organic electroluminescent device employing Alq ₃ which is widely used as an electron transport layer material. As a result, low voltage driving is possible, and luminous efficiency is excellent, so that it can be used for organic light emitting devices.

10: substrate 20: anode
30: hole injection layer 40: hole transport layer
50: organic light emitting layer 60: electron transport layer
70: electron injection layer 80: cathode

Claims (14)

A first electrode;
A second electrode facing the first electrode;
Including; an organic layer interposed between the first electrode and the second electrode,
The organic layer includes an electron transport layer and a light emitting layer,
The electron transport layer is used by mixing an anthracene derivative represented by the following [Formula A] and a compound represented by the following Formula B,
The organic light emitting device, characterized in that the mixing ratio of the anthracene derivative represented by the following [Chemical Formula A] and the compound represented by the following Formula B is in the range of 10:90 to 90:10 by weight.
[Formula A]

In the above [Formula A],
The Y is the same or different, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted carbon number of 1 to 30 It is any one selected from the silyl group of;
Z is the same or different, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted silyl having 1 to 30 carbon atoms It is any one selected from group;
m and m'are integers from 1 to 8;
When the substituents Y and Z are not bonded to carbon of the aromatic ring of the naphthyl group or anthracenyl group, hydrogen is bonded;
Each of X ₁ to X ₅ is the same as or different from each other, and independently hydrogen, deuterium, 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 A cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, a cyano group, a nitro group, a halogen group, and a group adjacent to each other Can form aliphatic, aromatic condensed rings;
One or two of the substituents X ₁ to X ₅ are the following substituents 102 to 110, substituents 112, substituents 113, substituents 202, substituents 203, substituents 205, substituents 206, substituents 306, substituents 403 to substituents 405, substituents 407 to substituents 413, substituent 502, substituent 503, substituent 601 to substituent 606;
[Substituent 102] [Substituent 103]

[Substituent 104] [Substituent 105] [Substituent 106]

[Substituent 107] [Substituent 108] [Substituent 109]

[Substituent 110] [Substituent 112] [Substituent 113]

[Substituent 202] [Substituent 203]

[Substituent 205] [Substituent 206]

[Substituent 306] [Substituent 403]

[Substituent 404] [Substituent 405]

[Substituent 407] [Substituent 408] [Substituent 409]

[Substituent 410] [Substituent 411] [Substituent 412] [Substituent 413]

[Substituent 502] [Substituent 503]

[Substituent 601] [Substituent 602] [Substituent 603]

[Substituent 604] [Substituent 605] [Substituent 606]

Here, R is the same or different and independently of each other, hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C3-C3 It may be selected from a cycloalkyl group of 60, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkyl silyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and , Each substituent may be fused with a group adjacent to each other to form a ring,
n is an integer from 0 to 9,
The substituent 102 to the substituent 110, the substituent 112, the substituent 113, the substituent 202, the substituent 203, the substituent 205, the substituent 206, the substituent 306, the substituent 403 to the substituent 405, the substituent 407 to the substituent 413, the substituent 502, the substituent 503, the substituent 601 to the substituent When the substituent R is not bonded to the carbon of the aromatic ring in the heteroaryl group of 606, hydrogen is bonded,
One of R is a single bond bonded to the phenyl group of [Formula A].
The'substituted' in the'substituted or unsubstituted' is deuterium, a cyano group, a halogen group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, and At least one substituent selected from the group consisting of an arylalkyl group of 6 to 24, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, and an arylsilyl group having 1 to 24 carbon atoms Means to be substituted with.
[Formula B]

In the above [Formula B],
The M is lithium, and the OA is a monovalent ligand capable of single bond or coordination bond with the M,
O is oxygen,
A is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroatom O, N Or any one selected from a C2-C50 heteroaryl group having S,
When M is one metal selected from alkali metals, m = 1, n = 0,
When M is one metal selected from alkaline earth metals, m=1, n=1, or m=2, n=0,
When M is boron or aluminum, m is any one of 1 to 3, and n is any one of 0 to 2, satisfying m+n=3;
Each of Y is the same or different, and is independently any one selected from the following [Structural Formula C1] to [Structural Formula C39].
[Structural Formula C1] [Structural Formula C2] [Structural Formula C3]

[Structural Formula C4] [Structural Formula C5] [Structural Formula C6]

[Structural Formula C7] [Structural Formula C8] [Structural Formula C9] [Structural Formula C10]

[Structural Formula C11] [Structural Formula C12] [Structural Formula C13]

[Structural Formula C14] [Structural Formula C15] [Structural Formula C16]

[Structural Formula C17] [Structural Formula C18] [Structural Formula C19] [Structural Formula C20]

[Structural Formula C21] [Old Breakfast C22] [Structural Formula C23]

[Structural Formula C24] [Structural Formula C25] [Structural Formula C26]

[Structural Formula C27] [Structural Formula C28] [Structural Formula C29] [Structural Formula C30]

[Structural Formula C31] [Structural Formula C32] [Structural Formula C33]

[Structural Formula C34] [Structural Formula C35] [Structural Formula C36]

[Structural Formula C37] [Structural Formula C38] [Structural Formula C39]

In the [Structural Formula C1] to [Structural Formula C39],
The R is the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted Among the heteroaryl groups having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 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 Any one selected, may be connected to an adjacent substituent and an alkylene or alkenylene to form a spiro ring or a fused ring.
However, herein, the'substitution' in the'substituted or unsubstituted' means substituted with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, and nitro group. The method of claim 1,
Y and Z of the [Formula A] are each the same or different, and independently of each other, hydrogen, deuterium; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; It is one selected from among, wherein m and m'are each an integer of 1 to 4, characterized in that, anthracene derivative delete delete delete delete The method of claim 1,
Only one of the substituents X ₁ to X ₅ of [Formula A] is the substituent 102 to the substituent 110, the substituent 112, the substituent 113, the substituent 202, the substituent 203, the substituent 205, the substituent 206, the substituent 306, the substituent 403 to the substituent 405, a substituent Anthracene derivative, characterized in that it is any one of substituents selected from 407 to 413, substituent 502, substituent 503, and substituent 601 to substituent 606. A first electrode;
A second electrode facing the first electrode; And
An organic light-emitting device comprising; an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises at least one anthracene derivative of any one of claims 1, 2, and 7 . The method of claim 1,
The organic layer further comprises at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function, and an electron injection layer at the same time. delete The method of claim 1,
The light emitting layer is an organic light emitting device, characterized in that consisting of a host and a dopant.
delete delete delete

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