KR20230104005A - Anthracene derivative compound and an organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to an anthracene derivative compound having a characteristic structure in which an aliphatic aromatic mixed ring group is substituted and an organic light emitting device including the same, wherein the anthracene derivative compound according to the present invention is employed as a host of a light emitting layer and has a characteristic structure. It relates to a high-efficiency, long-life organic light-emitting device with remarkably improved luminous efficiency and lifespan characteristics by employing as a dopant of a light emitting layer.

Description

Anthracene derivative compound and an organic light emitting device comprising the same {Anthracene derivative compound and an organic light emitting device comprising the same}

The present invention relates to an anthracene derivative compound having a characteristic structure in which an aliphatic aromatic mixed ring group is substituted, and an organic light emitting device including the same, and more particularly, to an anthracene derivative compound according to the present invention as a host of a light emitting layer and having a characteristic structure It relates to a high-efficiency, long-life organic light-emitting device having remarkably improved luminous efficiency and lifespan characteristics by employing a polycyclic compound having a polycyclic ring as a dopant of a light emitting layer.

In the organic light emitting device, electrons injected from the electron injection electrode (cathode electrode) and holes injected from the hole injection electrode (anode electrode) are combined in the light emitting layer to form excitons, and the excitons generate energy. It is a self-luminous device that emits light while emitting, and such an organic light emitting device has a low driving voltage, high luminance, wide viewing angle, and fast response speed, and is in the limelight as a next-generation light source due to the advantages of being applicable to full-color flat light emitting displays. .

In order for such an organic light emitting device to exhibit the above characteristics, the structure of the organic layer in the device is optimized, and materials constituting each organic layer, such as a hole injection material, a hole transport material, a hole blocking material, a light emitting material, an electron transport material, and an electron injection material However, it is necessary to precede that the electronic blocking material is supported by a stable and efficient material, but there is still a need to develop a stable and efficient organic layer structure for an organic light emitting device and each material.

In particular, in order to obtain maximum efficiency in the light emitting layer, an appropriate combination of energy band gaps between the host and the dopant is required so that holes and electrons can move to the dopant through a stable electrochemical path and form excitons.

In addition, when the molecules used in each organic layer are layered to form crystals during OLED device manufacturing, recrystallization occurs due to heat generated during deposition, resulting in cracks and reducing the lifespan of the device. This problem can be solved. There is an urgent need for the development of materials and device structures having characteristic structures.

Therefore, in order to solve the above problems, the present invention is a host material having a characteristic structure in which an aliphatic aromatic mixed cyclic group is substituted for a light emitting layer in an organic light emitting device, and a high efficiency long lifespan with significantly improved luminous efficiency and lifetime characteristics by employing the same. It is intended to provide an organic light emitting device.

In order to solve the above problems, the present invention provides an anthracene derivative compound represented by the following [Formula 1] used as a host compound for an organic layer in a device, preferably a light emitting layer.

[Formula 1]

The characteristic structure of [Formula 1], each substituent, and the specific compound implemented accordingly will be described later.

In addition, in order to solve the above problems, the present invention includes a first electrode, a second electrode opposite to the first electrode, and a light emitting layer interposed between the first electrode and the second electrode, and the [Formula 1] An organic light emitting device including the anthracene derivative compound shown as a host in an emission layer is provided.

According to an embodiment of the present invention, the emission efficiency and lifetime characteristics are improved by employing a polycyclic compound represented by the following [Formula 2] as a dopant while including the anthracene derivative compound represented by [Formula 1] as a host in the light emitting layer. An organic light emitting device with significantly improved high efficiency and long lifespan is provided.

[Formula 2]

The characteristic structure of [Formula 2], definitions of each substituent, and specific compounds realized thereby will be described later.

The present invention relates to an anthracene derivative compound having a characteristic structure in which an aliphatic aromatic mixed cyclic group is substituted, and an organic light emitting device including the anthracene derivative compound as a host material in a light emitting layer is a high-efficiency, long-life organic light emitting device having excellent device characteristics such as luminous efficiency and lifetime characteristics. Since a light emitting device can be implemented, it can be usefully used in various display devices such as flat, flexible, and wearable displays as well as lighting devices.

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

One aspect of the present invention relates to an anthracene derivative compound represented by the following [Formula 1], which is characterized in that various substituents are introduced into a characteristic structure in which an aliphatic aromatic mixed ring group is substituted, and through which various substituents are applied to the light emitting layer of an organic light emitting device. Employed as a host compound, it is possible to implement a high-efficiency, long-life organic light emitting device.

In general, when molecules used in each organic layer are piled up to form crystals during the manufacture of OLED devices, recrystallization occurs due to heat generated during deposition, resulting in cracks and a problem in that the lifetime of the device is reduced.

In the present invention, in order to prevent the problems caused by the above phenomenon, by introducing a bulky substituent at a characteristic position in the molecule, the regular arrangement of the molecules is disturbed, thereby weakening the intermolecular binding force and thereby making it difficult to form a crystal. By increasing the non-crystallized amorphous portion to suppress the decrease in lifespan and at the same time introducing bulky substituents, quenching of excitons due to 2-dimensional and 3-dimensional interactions between molecules can also be suppressed, thereby increasing the luminous efficiency at the same time. effect can be achieved.

In addition, the compound according to the present invention supplements the shortcoming of low lifespan found in conventional moieties by seeking an additional increase in lifespan by replacing a certain portion of hydrogen in the formula with deuterium.

[Formula 1]

In the above [Formula 1],

A is the same as or different from each other, and is any one selected from O, S, and CR ₃ R ₄ .

o and m are integers of 1 or 2, and when o or m is 2 or more, the plurality of A's are the same as or different from each other.

R, R ₃ and R ₄ are the same as or different from each other and each independently represents hydrogen, heavy hydrogen, and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In addition, the adjacent R, R ₃ and R ₄ may be linked to each other or adjacent substituents to further form an alicyclic or aromatic monocyclic or polycyclic ring.

R ₁ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, or a substituted or unsubstituted 2 to 50 carbon atoms. It is selected from a 50 heterocycloalkyl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms.

l is an integer of 3, the plurality of R ₁ are the same as or different from each other, provided that at least one of the R ₁ is not hydrogen or deuterium.

According to one embodiment of the present invention, at least one of the plurality of R ₁ in [Formula 1] may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

R ₂ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon atom having 2 to 30 carbon atoms. Alkenyl group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, substituted or unsubstituted carbon atoms Heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted It is selected from a germanium group, a nitro group, a cyano group, and a halogen group.

n is an integer of 8, and the plurality of R ₂ are the same as or different from each other.

Ar ₁ is a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms.

Ar ₂ is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 2 to 50 carbon atoms; to 50 heteroaryl groups.

According to one embodiment of the present invention, at least 4 or more of the plurality of R ₂ of the [Formula 1] may be deuterium.

'Substitution' in 'substituted or unsubstituted' in [Formula 1] is deuterium, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, and a cycloalkyl group having 2 to 24 carbon atoms. Alkenyl group, C2-24 alkynyl group, C1-24 heteroalkyl group, C2-24 heterocycloalkyl group, C6-30 aryl group, C7-30 arylalkyl group, C7-30 alkyl An aryl group, a heteroaryl group having 2 to 30 carbon atoms, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkylheteroaryl group having 3 to 30 carbon atoms, an aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, Aryloxy group having 6 to 24 carbon atoms, arylthionyl group having 6 to 24 carbon atoms, amine group having 1 to 40 carbon atoms, silyl group having 1 to 40 carbon atoms, germanium group having 1 to 40 carbon atoms, cyano group, halogen group, hydroxy group And means substituted with one or more substituents selected from the group consisting of a nitro group, and one or more hydrogens in each substituent may be substituted with deuterium.

According to one embodiment of the present invention, [Formula 1] may be an anthracene derivative compound represented by the following [Formula 1-1] or [Formula 1-2].

[Formula 1-1] [Formula 1-2]

In [Formula 1-1] and [Formula 1-2], R ₁ , R ₂ , Ar ₁ , Ar ₂ , A, R, l, m, n and o are the same as defined in [Formula 1] above. .

In addition, according to an embodiment of the present invention, the [Formula 1-1] is represented by the following [Formula 1-3], and the [Formula 1-2] is represented by the following [Formula 1-4]. It may be an anthracene derivative compound to be.

[Formula 1-3] [Formula 1-4]

In [Formula 1-3] and [Formula 1-4],

X is O or S.

R ₅ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, an alkyl group having 1 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a carbon atom having 3 to 24 carbon atoms. Cycloalkyl group of 24, heterocycloalkyl group of 2 to 24 carbon atoms, heteroaryl group of 2 to 30 carbon atoms, aliphatic aromatic mixed ring group of 3 to 30 carbon atoms, arylalkyl group of 7 to 30 carbon atoms, alkylaryl group of 7 to 30 carbon atoms , C3 to C30 heteroarylalkyl group, C3 to C30 alkylheteroaryl group, C1 to C24 alkoxy group, C6 to C24 aryloxy group, C1 to C24 alkylthioxy group, C5 to 24 carbon atoms Any one selected from an arylthiooxy group, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group, wherein R ₅ In the substituent One or more hydrogens may be replaced by deuterium.

In addition, the plurality of adjacent R ₅ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

p is an integer of 7, and the plurality of R ₅ are the same as or different from each other.

R ₁ , R ₂ , Ar ₁ , A, R, l, m, n and o are the same as defined in [Formula 1] above.

In addition, another aspect of the present invention relates to an organic light emitting device composed of a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer, preferably a light emitting layer It is characterized by comprising an anthracene derivative compound represented by [Formula 1], and a polycyclic compound represented by [Formula 2] below while including the anthracene derivative compound represented by [Formula 1] as a host in the light emitting layer. may be included together as a dopant.

[Formula 2]

In the above [Formula 2],

X ₁ is B, Y ₁ and Y ₂ are the same as or different from each other, and are each independently any one selected from NR ₁₁ , O, S, CR ₁₂ R ₁₃ , SiR ₁₄ R ₁₅ and GeR ₁₆ R ₁₇ .

A ₁ to A ₃ are the same as or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 50 carbon atoms, or a substituted or unsubstituted carbon atom 2 to 50 aromatic heterocycles, substituted or unsubstituted C2-50 aliphatic heterocycles, and substituted or unsubstituted C3-50 aliphatic aromatic mixed rings.

R ₁₁ to R ₁₇ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted An alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted Unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms An aryloxy group, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, and a substituted or an unsubstituted germanium group, a nitro group, a cyano group, and a halogen group.

In addition, R ₁₁ to R ₁₇ may be connected to the A ₁ to A ₃ rings to further form an alicyclic or aromatic monocyclic or polycyclic ring.

In addition, R ₁₂ and R ₁₃ , R ₁₄ and R ₁₅ , and R ₁₆ and R ₁₇ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

In addition, 'substitution' in 'substituted or unsubstituted' in [Formula 2] is deuterium, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, and a carbon atom having 2 to 24 carbon atoms. 24 alkenyl group, C2-24 alkynyl group, C1-24 heteroalkyl group, C2-24 heterocycloalkyl group, C6-30 aryl group, C7-30 arylalkyl group, C7-30 Alkylaryl group, C2-30 heteroaryl group, C3-30 heteroarylalkyl group, C3-30 alkylheteroaryl group, C3-30 aliphatic aromatic mixed ring group, C1-24 alkoxy group, aryloxy group having 6 to 24 carbon atoms, arylthionyl group having 6 to 24 carbon atoms, amine group having 1 to 40 carbon atoms, silyl group having 1 to 40 carbon atoms, germanium group having 1 to 40 carbon atoms, cyano group, halogen group , It means that it is substituted with one or more substituents selected from the group consisting of a hydroxyl group and a nitro group, and one or more hydrogens in each substituent can be substituted with deuterium.

According to one embodiment of the present invention, [Formula 2] may be a polycyclic compound represented by [Formula 3] or [Formula 4] below.

[Formula 3] [Formula 4]

In [Formula 3] and [Formula 4],

Y ₃ is O, S or NR ₁₈ , R ₁₈ is the same as the definition of R ₁₁ to R ₁₇ in [Formula 2], and Y ₁ , Y ₂ and A ₁ to A ₃ are equal to the definition

Further, according to one embodiment of the present invention, [Formula 2] may be a polycyclic compound represented by any one selected from the following [Formula 3-1] to [Formula 4-3].

[Formula 3-1] [Formula 4-1]

In [Formula 3-1] and [Formula 4-1],

Z ₁ to Z ₁₀ are the same as or different from each other, each independently represent CR ₃₁ or N, and when two or more of Z ₁ to Z ₁₀ are each CR ₃₁ , each CR ₃₁ is identical to or different from each other.

When two or more of Z ₁ to Z ₁₀ are each CR ₃₁ , each adjacent R ₃₁ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

Y ₃ is O, S or NR ₁₈ , and R ₁₈ has the same definition as R ₁₁ to R ₁₇ in [Formula 2].

R ₃₁ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon atom having 2 to 30 carbon atoms. 30 alkenyl group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, substituted or unsubstituted Heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms Group, 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 amine group, substituted or unsubstituted silyl group, substituted or unsubstituted It is any one selected from a germanium group, a nitro group, a cyano group, and a halogen group.

R ₂₁ to R ₃₀ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, an alkyl group having 1 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an aryl group having 6 to 30 carbon atoms, A cycloalkyl group having 3 to 24 carbon atoms, a heterocycloalkyl group having 2 to 24 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, and a heteroaryl group having 3 to 30 carbon atoms. Alkylaryl group, C3-30 heteroarylalkyl group, C3-30 alkylheteroaryl group, C1-24 alkoxy group, C6-24 aryloxy group, C1-24 alkylthioxy group, carbon number Any one selected from an arylthiooxy group of 5 to 24, an amine group of 1 to 30 carbon atoms, a silyl group of 1 to 30 carbon atoms, a germanium group of 1 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group, wherein R ₂₁ to R ₃₀ , one or more hydrogens in the substituents may be substituted with deuterium.

Each adjacent substituent among R ₂₁ to R ₃₀ may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

The plurality of R ₃₁ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

The R ₂₁ , R ₂₅ , R ₂₆ and R ₃₀ may further form an alicyclic or aromatic monocyclic or polycyclic ring by combining with each of R ₃₁ when each adjacent Z ₈ and Z ₉ is CR ₃₁ . .

Wherein Y _One And Y ₂ are the same as or different from each other, and each independently the same as defined in [Formula 2] or a linking group represented by [Structural Formula A] below, but at least one of Y _One and Y ₂ is the following [Structural Formula It is characterized by being a linking group represented by A].

[Structural Formula A]

In the above [structural formula A],

R ₄₁ to R ₄₅ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, an alkyl group having 1 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an aryl group having 6 to 30 carbon atoms, A cycloalkyl group having 3 to 24 carbon atoms, a heterocycloalkyl group having 2 to 24 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, and a heteroaryl group having 3 to 30 carbon atoms. Alkylaryl group, C3-30 heteroarylalkyl group, C3-30 alkylheteroaryl group, C1-24 alkoxy group, C6-24 aryloxy group, C1-24 alkylthioxy group, carbon number Any one selected from an arylthiooxy group having 5 to 24, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group, wherein R ₄₁ to R ₄₅ , one or more hydrogens in the substituents may be substituted with deuterium.

The R ₄₁ to R ₄₅ may be linked to adjacent substituents to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[Formula 3-2] [Formula 4-2]

In [Formula 3-2] and [Formula 4-2],

Z ₁ to Z ₁₀ are the same as or different from each other, each independently represent CR ₃₁ or N, and when two or more of Z ₁ to Z ₁₀ are each CR ₃₁ , each CR ₃₁ is identical to or different from each other.

When two or more of Z ₁ to Z ₈ are each CR ₃₁ , each adjacent R ₃₁ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

Y ₃ is O, S or NR ₁₈ , and R ₁₈ has the same definition as R ₁₁ to R ₁₇ in [Formula 2].

M is Si or Ge.

R ₃₁ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon atom having 2 to 30 carbon atoms. 30 alkenyl group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, substituted or unsubstituted Heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms Group, 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 amine group, substituted or unsubstituted silyl group, substituted or unsubstituted It is any one selected from a germanium group, a nitro group, a cyano group, and a halogen group.

R ₄₆ to R ₄₈ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, or a substituted or unsubstituted carbon atom. Alkenyl group having 2 to 24 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 24 carbon atoms, substituted or unsubstituted Cyclic heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 24 carbon atoms, substituted or unsubstituted C6 to 24 carbon atoms Aryloxy group, substituted or unsubstituted C1-24 alkylthioxy group, substituted or unsubstituted C5-24 C5-24 arylthio group, substituted or unsubstituted C1-30 amine group, substituted or unsubstituted It is any one selected from a silyl group having 1 to 30 carbon atoms, a substituted or unsubstituted germanium group having 1 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group.

One or more hydrogens in the substituents of R ₃₁ and R ₄₆ to R ₄₈ may be substituted with deuterium,

Each of the substituents of R ₄₆ to R ₄₈ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[Formula 3-3] [Formula 4-3]

In [Formula 3-3] and [Formula 4-3],

Z ₁ to Z ₁₁ are the same as or different from each other, and each independently represent CR ₃₁ or N, and when two or more of Z ₁ to Z ₁₁ are each CR ₃₁ , each CR ₃₁ is identical to or different from each other.

When two or more of Z ₁ to Z ₁₁ are CR ₃₁ respectively, each adjacent R ₃₁ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

Y ₃ is O, S or NR ₁₈ , and R ₁₈ has the same definition as R ₁₁ to R ₁₇ in [Formula 2].

R ₃₁ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon atom having 2 to 30 carbon atoms. 30 alkenyl group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, substituted or unsubstituted Heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms Group, 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 amine group, substituted or unsubstituted silyl group, substituted or unsubstituted It is any one selected from a germanium group, a nitro group, a cyano group, and a halogen group, and one or more hydrogens in the substituent of R ₃₁ may be substituted with deuterium.

Wherein Y _One And Y ₂ are the same as or different from each other, and each independently the same as defined in [Formula 2] or a linking group represented by [Structural Formula B] below, but at least one of Y _One and Y ₂ is the following [Structural Formula It is characterized in that it is a linking group represented by B].

[Structural Formula B]

In the [structural formula B],

X ₂ is O or S;

R ₅₁ to R ₅₈ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, an alkyl group having 1 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an aryl group having 6 to 30 carbon atoms, A cycloalkyl group having 3 to 24 carbon atoms, a heterocycloalkyl group having 2 to 24 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, and a heteroaryl group having 3 to 30 carbon atoms. Alkylaryl group, C3-30 heteroarylalkyl group, C3-30 alkylheteroaryl group, C1-24 alkoxy group, C6-24 aryloxy group, C1-24 alkylthioxy group, carbon number Any one selected from an arylthiooxy group having 5 to 24, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group, wherein R ₅₁ One or more hydrogens in the substituents of to R ₅₈ may be substituted with deuterium.

Any one of R ₅₁ to R ₅₈ is a single bond bonded to the nitrogen atom, and the remaining R ₅₁ to R ₅₈ excluding the single bond are linked to adjacent substituents to form an alicyclic or aromatic monocyclic or polycyclic ring. can

'Substitution' in 'substituted or unsubstituted' in [Formula 3-1] to [Formula 4-3] refers to heavy hydrogen, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, and a carbon atom having 3 to 24 carbon atoms. Cycloalkyl group, C2-24 alkenyl group, C2-24 alkynyl group, C1-24 heteroalkyl group, C2-24 heterocycloalkyl group, C6-30 aryl group, C7-30 Arylalkyl group, C7-30 alkylaryl group, C2-30 heteroaryl group, C3-30 heteroarylalkyl group, C3-30 alkylheteroaryl group, C3-30 aliphatic aromatic mixed ring group , C1-24 alkoxy group, C6-24 aryloxy group, C6-24 arylthionyl group, C1-40 amine group, C1-40 silyl group, C1-40 low ma It means that it is substituted with one or more substituents selected from the group consisting of a nium group, a cyano group, a halogen group, a hydroxyl group, and a nitro group, and one or more hydrogens in each substituent can be substituted with deuterium.

In this case, the content of the dopant in the light emitting layer of the organic light emitting device according to the present invention may be typically selected from 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, and the dopant in the light emitting layer is a mixture of one or more compounds other than one or more compounds represented by [Formula 2]. Alternatively, it may be used by being laminated, and the host in the light emitting layer may be used by mixing or stacking one or more other compounds in addition to one or more compounds represented by [Formula 1].

On the other hand, in the present invention, the carbon number range of the alkyl or aryl group in the 'substituted or unsubstituted alkyl group having 1 to 30 carbon atoms', 'substituted or unsubstituted aryl group having 6 to 50 carbon atoms', etc. It means the total number of carbon atoms constituting the alkyl part or the aryl part when viewed as unsubstituted without considering the substituted part. For example, a phenyl group in which a butyl group is substituted at the para position corresponds to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

In addition, in the present invention, the meaning of further forming a ring by being linked to each other or adjacent groups means that adjacent substituents among the specified substituents are bonded from each other, or specified substituents and other adjacent groups are bonded to each other to form substituted or unsubstituted alicyclic groups, It means that it can form an aromatic ring, and 'adjacent group' means a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located three-dimensionally closest to the substituent, or an atom on which the substituent is substituted. It may mean another substituent substituted on. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring can be interpreted as 'adjacent groups', and a pair of substituents connected to each other are one from each other. By removing the hydrogen radicals of and connecting them, an additional ring is formed, and the carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring can be replaced with a hetero atom such as N, NR, O, S, Si, Ge, R is the same as the definition of R ₁ to R ₆ .

In the present invention, the alkyl group may be a straight chain or branched chain, and specific examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1- Methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group , cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1 -Ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but is not limited to these.

In the present invention, specific examples of the arylalkyl group include, but are not limited to, phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl, and naphthylethyl.

In the present invention, specific examples of the alkylaryl group include tolyl, xylenyl, dimethylnaphthyl, t-butylphenyl, t-butylnaphthyl, and t-butylphenanthryl, but are not limited thereto.

In the present invention, the alkenyl group includes a straight chain or branched chain, and may be further substituted by other substituents, specifically, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, and a 2-butene group. Nyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1-butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group , 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl -1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but is not limited thereto.

In the present invention, the alkynyl group also includes a straight chain or branched chain, and may be further substituted by other substituents, and may include ethynyl, 2-propynyl, etc., but is limited thereto It doesn't work.

In the present invention, the cycloalkenyl group is a cyclic unsaturated hydrocarbon group that has one or more carbon double bonds and is not an aromatic ring, and includes cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, 1, 3-cyclohexadienyl group, 1,4-cyclohexadienyl group, 2,4-cycloheptadienyl group, 1,5-cyclooctadienyl group, and the like, but are not limited thereto.

In the present invention, the aromatic hydrocarbon ring or aryl group may be monocyclic or polycyclic, and polycyclic means a group directly connected or condensed with another ring group, and the other ring group may be an aromatic hydrocarbon ring, but other types of rings groups such as aliphatic heterocycles, aliphatic hydrocarbon rings, aromatic heterocycles and the like. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, and examples of the polycyclic aryl group include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group, and chrysenyl group. group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthene group, etc., but the scope of the present invention is not limited only to these examples.

In the present invention, the aromatic heterocycle or heteroaryl group is an aromatic ring containing at least one of hetero atoms, examples of which include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, and an oxadia group. sol group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group , pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, indolocarbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group , benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, pheno Thiazinyl group and the like, but are not limited thereto.

In the present invention, an aliphatic hydrocarbon ring or cycloalkyl group is a non-aromatic ring and means a ring composed of only carbon and hydrogen atoms, and includes monocyclic or polycyclic rings as examples, and may be further substituted by other substituents. A ring means a group directly linked or condensed with another ring group, and the other ring group may be an aliphatic hydrocarbon ring, but may also be another type of ring group, such as an aliphatic heterocycle, an aromatic hydrocarbon ring, or an aromatic heterocycle. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, adamantyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclo Cycloalkyl such as hexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, and cyclohexane, cyclohexyl group cycloalkanes such as pentane, and cyclocycloalkenes such as cyclohexene and cyclobutene, but are not limited thereto.

In the present invention, an aliphatic heterocycle or heterocycloalkyl group means an aliphatic ring containing at least one of heteroatoms, and includes heteroatoms such as O, S, Se, N or Si, and also monocyclic or polycyclic. It may be further substituted by other substituents, and polycyclic refers to a group in which heterocycloalkyl, heterocyclane, etc. are directly connected or condensed with another ring group, and the other ring group may be an aliphatic heterocyclic ring, Other types of ring groups, such as aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aromatic heterocycles, and the like may also be used.

In the present invention, the aliphatic aromatic mixed ring (group) means a ring in which two or more rings are connected and condensed, and an aliphatic ring and an aromatic ring are condensed to have non-aromaticity as a whole, and more specifically Is an aromatic hydrocarbon ring condensed cycloalkyl group, an aromatic hetero ring condensed cycloalkyl group, an aromatic hydrocarbon ring condensed heterocycloalkyl group, an aliphatic hydrocarbon ring condensed aryl group, an aliphatic hydrocarbon ring condensed heteroaryl group, an aliphatic hetero It may be an aryl group in which a ring is condensed, a heteroaryl group in which an aliphatic hetero ring is condensed, and the like. and a rene group, a tetrahydrobenzothiophene group, a tetrahydrobenzofuranyl group, a tetrahydrocarbazole group, and a tetrahydroquinoline group. In addition, heteroatoms such as N, O, S, Si, Ge, and P may be included in addition to carbon in the polycyclic aliphatic-aromatic mixed ring.

In the present invention, the alkoxy group may be specifically methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, etc., but is not limited thereto.

In the present invention, the silyl group may include -SiH ₃ , an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, an arylheteroarylsilyl group, a heteroarylsilyl group, and the like, and the arylsilyl group is -SiH ₃ In In SiH ₃ , an alkylsilyl group means an amine in which one or two or three hydrogens are substituted with an alkyl group, and an alkylarylsilyl group is - In SiH ₃ , each of at least one hydrogen is substituted with an alkyl group and an aryl group to mean a silyl group including one or two alkyl groups and two or one aryl groups corresponding thereto, and the arylheteroarylsilyl group is -SiH ₃ In each, at least one hydrogen is substituted with an aryl group and a heteroaryl group to mean a silyl group including one or two aryl groups and two or one heteroaryl group corresponding thereto, and the heteroarylsilyl group is -SiH ₃ In this case, it means a silyl group in which one or two or three hydrogens are substituted with a heteroaryl group, and examples of the arylsilyl group include a substituted or unsubstituted monoarylsilyl group, a substituted or unsubstituted diarylsilyl group, or There is a substituted or unsubstituted triarylsilyl group, and the same applies to the alkylsilyl group and the heteroarylsilyl group.

Here, each of the aryl groups in the arylsilyl group, the heteroarylsilyl group, and the arylheteroarylsilyl group may be a monocyclic aryl group or a polycyclic aryl group, and the arylsilyl group, the heteroarylsilyl group, and the arylheteroarylsilyl group Each heteroaryl group in may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

In addition, specific examples of the silyl group 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 present invention, the amine group may include -NH ₂ , an alkylamine group, an arylamine group, an alkylarylamine group, an arylheteroarylamine group, a heteroarylamine group, and the like, and the arylamine group is -NH ₂ , An amine in which one or two hydrogens are substituted with an aryl group, an alkylamine group in -NH ₂ means an amine in which one or two hydrogens are substituted with an alkyl, and an alkylarylamine group in -NH ₂ , One hydrogen represents an alkyl group and the other hydrogen represents an amine substituted with an aryl group, and the arylheteroarylamine group in -NH ₂ represents an amine in which one hydrogen is substituted with an aryl group and the other hydrogen is substituted with a heteroaryl group. The heteroarylamine group in -NH ₂ means an amine in which one or two hydrogens are substituted with a heteroaryl group, and examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted There is a cyclic diarylamine group or a substituted or unsubstituted triarylamine group, and the alkylamine group and the heteroarylamine group are also applicable.

Here, each aryl group in the arylamine group, the heteroarylamine group, and the arylheteroarylamine group may be a monocyclic aryl group or a polycyclic aryl group, and the arylamine group, the heteroarylamine group, and the arylheteroarylamine group Each heteroaryl group in may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. Or it may be a polycyclic aryl group, and each of the heteroaryl groups in the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

In the present invention, the germanium group (or germanium group) may include -GeH ₃ , an alkyl germanium group, an aryl germanium group, a heteroaryl germanium group, an alkyl aryl germanium group, an alkyl heteroaryl germanium group, an aryl heteroaryl germanium group, and the like. These definitions are as described in the silyl group, but may be applied to each substituent as a substituent obtained by substituting a germanium atom (Ge) instead of a silicon atom (Si) in the silyl group.

In addition, specific examples of the germanium group include trimethyl germane, triethyl germane, triphenyl germane, trimethoxy germane, dimethoxyphenyl germane, diphenylmethyl germane, diphenyl vinyl germane, methylcyclobutyl germane, dimethyl furyl germane, and the like. In addition, one or more hydrogen atoms of the germanium group may be substituted with the same substituent as that of the aryl group.

In the present invention, a cycloalkyloxy group, an aryloxy group, a heteroaryloxy group, a cycloalkylthio group, an arylthio group, and a cycloaryl group among heteroarylthio groups, aryl groups, and heteroaryl groups are the aforementioned cycloaryl groups, aryl groups, and the like. It is the same as an example of a group, a heteroaryl group, and specifically, for example, an aryloxy group, a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethyl Phenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl -2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, etc. Examples of the arylthioxy group include, but are not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, and a 4-tert-butylphenylthioxy group.

In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.

According to one embodiment of the present invention, the anthracene derivative compound represented by [Formula 1] may be any one selected from the compounds represented below, but the range is not limited thereby.

According to one embodiment of the present invention, the polycyclic compound represented by [Formula 2] may be any one selected from the compounds represented below, but the range is not limited thereby.

The organic layer of the organic light emitting device according to the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, and the like. However, it is not limited thereto and may include a smaller or larger number of organic layers, and an organic material layer structure of a preferable organic light emitting device according to the present invention will be described in more detail in the embodiments to be described later.

Hereinafter, an embodiment of the organic light emitting device according to the present invention will be described in more detail.

The organic light emitting device according to the present invention includes an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode, and may further include a hole injection layer between the anode and the hole transport layer, if necessary, and electron transport layer between the electron transport layer and the cathode. It may further include an injection layer, and in addition to that, it is possible to further form one or two intermediate layers, and a hole blocking layer or an electron blocking layer may be further formed. An organic layer having various functions may be further included according to characteristics.

Meanwhile, a detailed structure of an organic light emitting device according to an embodiment of the present invention, a manufacturing method thereof, and materials for each organic layer are as follows.

First, an anode is formed by coating a material for an anode electrode on a substrate. Here, as the substrate, a substrate used in a conventional organic light emitting 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.

A hole injection layer is formed by vacuum thermal evaporation or spin coating of a hole injection layer material on top of the anode electrode, and then a hole transport layer is formed by vacuum thermal evaporation or spin coating of a hole transport layer material on top of the hole injection layer. .

As long as the hole injection layer material is commonly used in the art, it may be used without particular limitation, and as a specific 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. can be used.

In addition, the hole transport layer material is not particularly limited as long as it is commonly used in the art, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1- Biphenyl] -4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD) or the like can be used.

Subsequently, a hole auxiliary layer and a light emitting layer may be sequentially stacked on top of the hole transport layer, and a hole blocking layer may be selectively formed on top of the light emitting layer by a vacuum deposition method or a spin coating method. The hole-blocking layer serves to prevent this problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level because the lifespan and efficiency of the device are reduced when holes pass through the organic light emitting layer and flow into the cathode. . At this time, the hole-blocking material used is not particularly limited, but should have electron transport ability and higher ionization potential than the light emitting compound, and typically BAlq, BCP, TPBI, and the like may be used.

As a material used for the hole blocking layer, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq ₂ , OXD-7, Liq, etc. may be used, but is not limited thereto.

The present invention by forming an electron injection layer after depositing an electron transport layer on the hole blocking layer through a vacuum deposition method or a spin coating method, and vacuum thermally depositing a metal for forming a cathode on top of the electron injection layer to form a cathode electrode. An organic light emitting device according to an embodiment of is completed.

Here, the metal for forming the cathode is lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag) may be used, and a transmissive cathode using ITO or IZO may be used to obtain a top light emitting device.

As the material for the electron transport layer, a known electron transport material may be used to stably transport electrons injected from the cathode. Examples of known electron transport materials are quinoline derivatives, in particular tris(8-quinolinolate)aluminum (Alq3), TAZ, BAlq, beryllium bis(benzoquinolin-10-noate) (beryllium bis(benzoquinolin-10- olate: Bebq2) and oxadiazole derivatives (PBD, BMD, BND, etc.) can also be used.

In addition, each of the organic layers may be formed by a single molecule deposition method or a solution process, wherein the deposition method evaporates a material used as a material for forming each layer through heating or the like in a vacuum or low pressure state. It refers to a method of forming a thin film, and the solution process mixes a material used as a material for forming each layer with a solvent, and inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, and spin coating. It means a method of forming a thin film through the same method.

In addition, the organic light emitting device according to the present invention can be applied to a device selected from a flat panel display device, a flexible display device, a monochromatic or white flat panel lighting device, a monochromatic or white flexible lighting device, a vehicle display device, and a display device for virtual or augmented reality. can be used

synthesis example 1. [BH- 1] synthesis

synthesis example 1-1: Synthesis of A-1

<A-1a> <A-1>

100 g of <A-1a> and 800 mL of DMF were put in a reactor, and 103 g of NBS was slowly added dropwise thereto. After the dropwise addition, the mixture was stirred for 2 hours, water was added dropwise, and the solid was filtered. After dissolving in dichloromethane, washing with distilled water, dichloromethane was concentrated, methanol was added, and crystals were collected and dried to obtain <A-1>. (129 g, 91.3%)

synthesis example 1-2: Synthesis of A-2

<A-1> <A-2>

In a reactor, 30 g of <A-1> and 300 mL of tetrahydrofuran were dissolved and stirred at -78 ° C under a nitrogen atmosphere. 124 mL of normal butyl lithium was slowly added dropwise to the cooled reaction solution. After stirring at the same temperature for 2 hours, 15.2 g of trimethylboride was slowly added dropwise over 30 minutes, followed by stirring at room temperature overnight. After completion of the reaction, dihydrochloric acid was slowly added dropwise to acidify the mixture. After extracting with water and ethyl acetate and separating the organic layer, water was removed with magnesium sulfate. The material was crystallized from heptane after concentration under reduced pressure. The resulting solid was filtered and washed with heptane and toluene to obtain <A-2>. (16.3 g, 62.6%)

synthesis example 1-3: Synthesis of A-3

<A-3a> <A-3b> <A-3>

25 g of <A-3a>, 15.2 g of <A-3b>, 2 g of tetrakis(triphenylphosphine)palladium(0), 24.4 g of potassium carbonate, 200 mL of toluene, 200 mL of ethanol, and 100 mL of distilled water were added to the reactor. After stirring under reflux, the mixture was reacted for one day. After confirming the completion of the reaction by TLC, the temperature was lowered to room temperature, distilled water and ethyl acetate were added, and extraction was performed. Ethyl acetate was concentrated, purified by column chromatography, and recrystallized to obtain <A-3>. (21.5 g, 73.7%)

synthesis example 1-4: Synthesis of A-4

<A-3> <A-4>

While stirring, 10 g of <A-3> and 150 mL of dichloromethane were added to the reactor, 7.3 g of trifluoroacetic anhydride and 4 g of triethylamine were slowly added dropwise thereto, followed by stirring for 3 hours. The organic layer was separated with distilled water and dichloromethane, and the organic extract was dried over magnesium sulfate, concentrated in vacuo, and purified by column chromatography to obtain <A-4>. (10.3 g, 79.8%)

synthesis example 1-5: Synthesis of A-5

<A-4> <A-2> <A-5>

After dissolving 6 g of <A-4> and 3.6 g of <A-2> in 250 mL of THF in a reactor, 2 M potassium carbonate aqueous solution and 0.33 g of tetrakis(triphenylphosphine)palladium(0) were added, followed by 6 hours while heating and stirring. After the reaction was completed, the temperature was lowered to room temperature, and the resulting solid was filtered and dried, purified by column chromatography, and then recrystallized to obtain <A-5>. (4 g, 56.7%)

synthesis example 1-6: Synthesis of A-6

<A-5> <A-6>

<A-6> was obtained by synthesizing in the same manner except that <A-5> was used instead of <A-1a> used in Synthesis Example 1-1. (Yield 82.7%)

synthesis example 1-7: [BH- 1] synthesis

<A-6> <A-7a> [BH-1]

20 g of <A-6>, 9.5 g of <A-7a>, 0.2 g of palladium(II) acetate, 10 g of sodium tertiary butoxide, 0.5 g of BIDIME, and 210 mL of toluene were added to the reactor and stirred under reflux for 3 days. After confirming the completion of the reaction by TLC, the reaction temperature was lowered to room temperature, distilled water and ethyl acetate were added, and extraction was performed. Ethyl acetate was concentrated, purified by column chromatography, and recrystallized to obtain [BH-1]. (12 g, 52.1%)

MS (MALDI-TOF): m/z 664.36 [M ⁺ ]

synthesis example 2. [BH- 2] of synthesis

synthesis example 2-1: Synthesis of B-1

<A-3a> <B-1a> <B-1>

<B-1> was obtained by synthesizing in the same manner except that <B-1a> was used instead of <A-3b> used in Synthesis Example 1-3. (yield 84%)

synthesis example 2-2: Synthesis of B-2

<B-1> <B-2>

<B-2> was obtained by synthesizing in the same manner except that <B-1> was used instead of <A-3> used in Synthesis Example 1-4. (Yield 82.3%)

synthesis example 2-3: Synthesis of B-3

<B-2> <A-2> <B-3>

<B-3> was obtained by synthesizing in the same manner except that <B-2> was used instead of <A-4> used in Synthesis Example 1-5. (Yield 60.1%)

synthesis example 2-4: Synthesis of B-4

<B-3> <B-4>

<B-4> was obtained by synthesizing in the same manner except that <B-3> was used instead of <A-5> used in Synthesis Example 1-6. (Yield 92.1%)

synthesis example 2-5: [BH- 2] of synthesis

<B-4> <B-5a> [BH-2]

[BH-2] was synthesized in the same manner except that <B-4> was used instead of <A-6> used in Synthesis Example 1-7, and <B-5a> was used instead of <A-7a>. got (Yield 56.1%)

MS (MALDI-TOF): m/z 619.37 [M ⁺ ]

synthesis example 3. [BH- 3] of synthesis

synthesis example 3-1: Synthesis of C-1

<A-2> <C-1a> <C-1>

<C-1> was synthesized in the same manner except that <C-1a> was used instead of <A-3a> used in Synthesis Example 1-3, and <A-2> was used instead of <A-3b>. got (Yield 87%)

synthesis example 3-2: Synthesis of C-2

<C-1> <C-2a> <C-2>

<C-2> was synthesized in the same manner except that <C-1> was used instead of <A-3a> used in Synthesis Example 1-3, and <C-2a> was used instead of <A-3b>. got (Yield 84.6%)

synthesis example 3-3: Synthesis of C-3

<C-2> <C-3>

<C-3> was obtained by synthesizing in the same manner except that <C-2> was used instead of <A-1a> used in Synthesis Example 1-1. (Yield 93.2%)

synthesis example 3-4: [BH- 3] of synthesis

<C-3> <A-7a> [BH-3]

[BH-3] was obtained by synthesizing in the same manner except that <C-3> was used instead of <A-6> used in Synthesis Example 1-7. (Yield 57.6%)

MS (MALDI-TOF): m/z 614.34 [M ⁺ ]

synthesis example 4. [BH- 4] of synthesis

synthesis example 4-1: Synthesis of D-1

<D-1a> <D-1b> <D-1>

<D-1> was synthesized in the same manner except that <D-1a> was used instead of <A-3a> used in Synthesis Example 1-3, and <D-1b> was used instead of <A-3b>. got (Yield 79.2%)

synthesis example 4-2: Synthesis of D-2

<D-2a> <D-2>

<D-2> was obtained by synthesizing in the same manner except that <D-2a> was used instead of <A-1> used in Synthesis Example 1-2. (Yield 69.3%)

synthesis example 4-3: Synthesis of D-3

<B-2> <D-2> <D-3>

<D-3> was synthesized in the same manner except that <B-2> was used instead of <A-4> used in Synthesis Example 1-5, and <D-2> was used instead of <A-2>. got (Yield 57.1%)

synthesis example 4-4: Synthesis of D-4

<D-3> <D-4>

<D-4> was obtained in the same manner except that <D-3> was used instead of <A-1a> used in Synthesis Example 1-1. (Yield 87.6%)

synthesis example 4-5: [BH- 4] of synthesis

<D-4> <D-1> [BH-4]

[BH-4] was synthesized in the same manner except that <D-4> was used instead of <A-6> used in Synthesis Example 1-7 and <D-1> was used instead of <A-7a>. got (Yield 54.4%)

MS (MALDI-TOF): m/z 701.40 [M ⁺ ]

synthesis example 5. [BH- 5] of synthesis

synthesis example 5-1: [BH- 5] of synthesis

[BH-5] was obtained in the same manner as in Synthesis Example 1, except that pyridin-3-ylboronic acid was used instead of <A-3b> in Synthesis Example 1-3.

MS (MALDI-TOF): m/z 615.34 [M ⁺ ]

synthesis example 6. [BH- 6] of synthesis

synthesis example 6-1: Synthesis of F-1

<C-1a> <B-1a> <F-1>

<F-1> was synthesized in the same manner except that <C-1a> was used instead of <A-3a> used in Synthesis Example 1-3, and <B-1a> was used instead of <A-3b>. got (Yield 86.9%)

synthesis example 6-2: Synthesis of F-2

<F-1> <A-2> <F-2>

<F-2> was synthesized in the same manner except that <F-1> was used instead of <A-3a> used in Synthesis Example 1-3, and <A-2> was used instead of <A-3b>. got (Yield 83.1%)

synthesis example 6-3: Synthesis of F-3

<F-2> <F-3>

<F-3> was obtained by synthesizing in the same manner except that <F-2> was used instead of <A-1a> used in Synthesis Example 1-1. (Yield 89.4%)

synthesis example 6-4: [BH- 6] of synthesis

<F-3> <F-4a> [BH-6]

[BH-6] was synthesized in the same manner except that <F-3> was used instead of <A-6> used in Synthesis Example 1-7 and <F-4a> was used instead of <A-7a>. got (Yield 50.8%)

MS (MALDI-TOF): m/z 700.44 [M ⁺ ]

synthesis example 7. [BH- 7] synthesis

synthesis example 7-1: [BH- 7] synthesis

[BH-7] was obtained in the same manner as in Synthesis Example 3, except that phenanthrene-9-ylboronic acid was used instead of <A-7a> in Synthesis Example 3-4. (final yield 51.2%)

MS (MALDI-TOF): m/z 624.36 [M ⁺ ]

synthesis example 8. [BH- 8] synthesis

synthesis example 8-1: [BH- 8] synthesis

[BH-7] was obtained in the same manner as in Synthesis Example 2, except that dibenzo[b,d]thiophene-4ylboronic acid was used instead of <B-5a> in Synthesis Example 2-5. (final yield 49.4%)

MS (MALDI-TOF): m/z 635.35 [M ⁺ ]

synthesis example 9. [ BD - 1] synthesis

synthesis example 9-1: Synthesis of H-1

<H-1a> <H-1b> <H-1>

30 g of <H-1a>, 25.8 g of <H-1b>, 0.9 g of palladium acetate, 25.5 g of sodium tertiary butoxide, 2.5 g of bis(diphenylphosphino)-1,1'-binaphthyl, After adding 400 mL of toluene, the mixture was stirred under reflux for 24 hours. After completion of the reaction, the mixture was filtered and concentrated, and separated by column chromatography to obtain <H-1>. (32 g, 81.9%)

synthesis example 9-2: Synthesis of H-2

<H-1> <H-2a> <H-2>

<H-2a> was used instead of <H-1a> and <H-1> was used instead of <H-1b>, and <H-2a> was synthesized in the same manner as in Synthesis Example 9-1. > got (Yield 73.2%)

synthesis example 9-3: Synthesis of H-3

<H-3a> <H-3b> <H-3>

<H-3b> was used instead of <H-1a> used in Synthesis Example 9-1, and <H-3a> was synthesized in the same manner except that <H-3a> was used instead of <H-1b>. > got (Yield 76.9%)

synthesis example 9-4: Synthesis of H-4

<H-3> <H-1b> <H-4>

<H-4> was obtained in the same manner as in Synthesis Example 9-1, except that <H-3> was used instead of <H-1a>. (Yield 72.7%)

synthesis example 9-5: Synthesis of H-5

<H-2> <H-4> <H-5>

<H-2> was used instead of <H-1a> and <H-4> was used instead of <H-1b>, and <H-5> was synthesized in the same manner as in Synthesis Example 9-1. > got (yield 65.9%)

synthesis example 9-6: [ BD - 1] synthesis

<H-5> <BD-1>

Put <H-5> 20 g and tert-butylbenzene into the reactor. After adding 36 mL of tert-butyllithium dropwise at -78 °C, the mixture was stirred at 60 °C for 3 hours. Thereafter, nitrogen was blown to remove pentane. After adding 4 mL of boron tribromide dropwise at -78 °C, the mixture was stirred at room temperature for 1 hour, then 5.3 g of N,N-diisopropylethylamine was added dropwise at 0 °C and stirred at 120 °C for 2 hours. After completion of the reaction, an aqueous solution of sodium acetate was added, stirred, extracted with ethyl acetate, and the organic layer was concentrated and separated by column chromatography to obtain [BD-1]. (2.8 g, 14.4%)

MS (MALDI-TOF): m/z 943.51 [M ⁺ ]

synthesis example 10. [ BD - 2] of synthesis

synthesis example 10-1: Synthesis of I-1

<I-1a> <H-1b> <I-1>

<I-1> was obtained by synthesizing in the same manner except that <I-1a> was used instead of <H-1a> used in Synthesis Example 9-1. (Yield 79.8%)

synthesis example 10-2: Synthesis of I-2

<I-1> <I-2a> <I-2>

<I-2a> was used instead of <H-1a> used in Synthesis Example 9-1, and <I-1> was used instead of <H-1b>. > got (Yield 69.7%)

synthesis example 10-3: Synthesis of I-3

<H-3> <I-3a> <I-3>

<I-3> was synthesized in the same manner except that <H-3> was used instead of <H-1a> and <I-3a> was used instead of <H-1b> used in Synthesis Example 9-1. > got (Yield 70.3%)

synthesis example 10-4: Synthesis of I-4

<I-2> <I-3> <I-4>

<I-4> was synthesized in the same manner except that <I-2> was used instead of <H-1a> and <I-3> was used instead of <H-1b> used in Synthesis Example 9-1. > got (Yield 76.7%)

synthesis example 10-5: [ BD - 2] of synthesis

<I-4> [BD-2]

[BD-2] was obtained by synthesizing in the same manner except that <I-4> was used instead of <H-5> used in Synthesis Example 9-6. (Yield 17.4%)

MS (MALDI-TOF): m/z 971.5 [M ⁺ ]

Example 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 is set to 1 × 10 ^-7 torr, and then a film of 2-TNATA (400 ÅHT (200 Å) is formed on the ITO in order. As a light emitting layer, a host compound according to the present invention and After forming a film (250 Å) by mixing 3 wt% of the dopant compound [BD-1] or [BD-2] according to the present invention, [Formula E-1] as an electron transport layer (300 Å), an electron injection layer A film of Liq (10 Å) was sequentially formed, and a film of Al (1000 Å) as a cathode was formed to fabricate an organic light emitting device. The emission characteristics of the organic light emitting device were measured at 10 mA/cm ² .

[2-TNATA] [HT] [Formula E-1]

[BH-1] [BH-2] [BH-3]

[BH-4] [BH-5] [BH-6]

[BH-7] [BH-8]

comparative example 1 to 7

Organic light emitting devices for comparative examples use the following [RH-1] to [RH-4] instead of the compound according to the present invention as a host compound in the device structure of the above example, and use the dopant compound [RD-1] An organic light emitting device was manufactured in the same manner except for the point, and the emission characteristics of the organic light emitting device were measured at 10 mA/cm ² . The structures of [RH-1] to [RH-4] and [RD-1] are as follows.

[RH-1] [RH-2] [RH-3]

[RH-4] [RD-1]

division host dopant External quantum efficiency (%) Life (T97, hr) Example 1 BH-1 BD-1 7.7 172 Example 2 BH-2 BD-1 8.1 185 Example 3 BH-3 BD-1 8.3 176 Example 4 BH-4 BD-1 7.6 164 Example 5 BH-5 BD-1 7.4 146 Example 6 BH-6 BD-1 8.1 175 Example 7 BH-7 BD-1 7.5 181 Example 8 BH-8 BD-1 7.1 145 Example 9 BH-2 BD-2 8.5 188 Example 10 BH-3 BD-2 8.8 172 Example 11 BH-7 BD-2 8.0 174 Comparative Example 1 RH-1 BD-1 5.2 53 Comparative Example 2 RH-2 BD-1 6.4 98 Comparative Example 3 RH-3 BD-1 4.8 38 Comparative Example 4 RH-4 BD-1 6.2 87 Comparative Example 5 RH-2 BD-2 6.6 93 Comparative Example 6 RH-3 BD-2 5.1 35 Comparative Example 7 RH-2 RD-1 5.5 52

Looking at [Table 1], the organic light emitting device including the compounds implemented by [Formula 1] and [Formula 2] according to the present invention as a host and a dopant in the light emitting layer is a host represented by [Formula 1] according to the present invention It can be seen that the external quantum efficiency and lifespan characteristics are remarkably superior to the devices (Comparative Examples 1 to 7) employing the structural characteristics of the compound and the dopant compound represented by [Formula 2], respectively, and contrasting compounds.

This is because when the molecules used in each layer are piled up to form crystals during OLED device manufacturing, recrystallization occurs due to heat generated during deposition, resulting in cracks and reducing the lifespan of the device. In the present invention, this phenomenon is prevented. In order to prevent the regular arrangement of molecules by introducing a bulkier substituent such as an aryl group instead of a hydrogen or linear alkyl group in the aliphatic aromatic mixed ring group at position 9 or 10 of anthracene, the intermolecular binding force is weakened and thus crystal formation is prevented. By increasing the portion of the amorphous state that has not been crystallized due to difficulty, the decrease in lifetime can be suppressed, and at the same time, the quenching of excitons due to intermolecular interactions can be suppressed, so that the effect of simultaneously increasing the luminous efficiency can be realized.

In addition, the compound according to the present invention supplements the shortcoming of low lifespan found in conventional moieties by seeking an additional increase in lifespan by replacing a certain portion of hydrogen in a specific position of anthracene in the formula or in a substituent with deuterium.

Claims (15)

An anthracene derivative compound represented by the following [Formula 1]:
[Formula 1]

In the above [Formula 1],
A is the same as or different from each other, and each is any one selected from O, S, and CR ₃ R ₄ ;
R, R ₃ and R ₄ are the same as or different from each other, and are each independently any one selected from hydrogen, heavy hydrogen, and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms;
The adjacent R, R ₃ and R ₄ may be linked to each other or adjacent substituents to further form an alicyclic or aromatic monocyclic or polycyclic ring,
R ₁ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, or a substituted or unsubstituted 2 to 50 carbon atoms. Any one selected from a 50 heterocycloalkyl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms,
R ₂ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon atom having 2 to 30 carbon atoms. Alkenyl group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, substituted or unsubstituted carbon atoms Heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Any one selected from a germanium group, a nitro group, a cyano group, and a halogen group,
Ar ₁ is a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms,
Ar ₂ is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 2 to 50 carbon atoms; to any one selected from 50 heteroaryl groups;
l is an integer of 3, the plurality of R ₁ are the same as or different from each other,
However, at least one of R ₁ is not hydrogen or deuterium,
o and m are integers of 1 or 2, and when o or m is 2 or more, the plurality of A's are the same as or different from each other,
n is an integer of 8, the plurality of R ₂ are each the same as or different from each other;

'Substitution' in 'substituted or unsubstituted' in [Formula 1] is deuterium, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, and a cycloalkyl group having 2 to 24 carbon atoms. Alkenyl group, C2-24 alkynyl group, C1-24 heteroalkyl group, C2-24 heterocycloalkyl group, C6-30 aryl group, C7-30 arylalkyl group, C7-30 alkyl An aryl group, a heteroaryl group having 2 to 30 carbon atoms, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkylheteroaryl group having 3 to 30 carbon atoms, an aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, Aryloxy group having 6 to 24 carbon atoms, arylthionyl group having 6 to 24 carbon atoms, amine group having 1 to 40 carbon atoms, silyl group having 1 to 40 carbon atoms, germanium group having 1 to 40 carbon atoms, cyano group, halogen group, hydroxy group And means substituted with one or more substituents selected from the group consisting of a nitro group, and one or more hydrogens in each substituent may be substituted with deuterium. According to claim 1,
[Formula 1] is an anthracene derivative compound represented by the following [Formula 1-1] or [Formula 1-2]:
[Formula 1-1] [Formula 1-2]

In [Formula 1-1] and [Formula 1-2],
R ₁ , R ₂ , Ar ₁ , Ar ₂ , A, R, l, m, n and o are the same as defined in [Formula 1] in claim 1 above. According to claim 2,
[Formula 1-1] is represented by [Formula 1-3], and [Formula 1-2] is represented by [Formula 1-4] An anthracene derivative compound, characterized in that:
[Formula 1-3] [Formula 1-4]

In [Formula 1-3] and [Formula 1-4],
X is O or S;
R ₅ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, an alkyl group having 1 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a carbon atom group having 3 to 24 carbon atoms. Cycloalkyl group of 24, heterocycloalkyl group of 2 to 24 carbon atoms, heteroaryl group of 2 to 30 carbon atoms, aliphatic aromatic mixed ring group of 3 to 30 carbon atoms, arylalkyl group of 7 to 30 carbon atoms, alkylaryl group of 7 to 30 carbon atoms , C3 to C30 heteroarylalkyl group, C3 to C30 alkylheteroaryl group, C1 to C24 alkoxy group, C6 to C24 aryloxy group, C1 to C24 alkylthioxy group, C5 to 24 carbon atoms Any one selected from an arylthiooxy group, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group, wherein R ₅ In the substituent one or more hydrogens can be replaced by deuterium;
The plurality of adjacent R ₅ may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
p is an integer of 7, the plurality of R ₅ are the same as or different from each other;
R ₁ , R ₂ , Ar ₁ , A, R, l, m, n and o are the same as defined in [Formula 1] in claim 1 above. According to claim 1,
An anthracene derivative compound, characterized in that at least 4 or more of the plurality of R ₂ of the [Formula 1] are deuterium. According to claim 1,
An anthracene derivative compound, characterized in that at least one of the plurality of R ₁ of [Formula 1] is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. According to claim 1,
[Formula 1] is an anthracene derivative compound, characterized in that any one selected from the following compounds:

a first electrode; a second electrode opposed to the first electrode; And an organic layer interposed between the first electrode and the second electrode; includes,
The organic layer includes a light emitting layer, wherein the light emitting layer includes a host; and a dopant;
The host includes at least one anthracene derivative compound represented by the following [Formula 1], and the dopant includes at least one polycyclic compound represented by the following [Formula 2]:
[Formula 1]

In the above [Formula 1],
A is the same as or different from each other, and each is any one selected from O, S, and CR ₃ R ₄ ;
R, R ₃ and R ₄ are the same as or different from each other, and are each independently any one selected from hydrogen, heavy hydrogen, and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms;
The adjacent R, R ₃ and R ₄ may be linked to each other or adjacent substituents to further form an alicyclic or aromatic monocyclic or polycyclic ring,
R ₁ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, or a substituted or unsubstituted 2 to 50 carbon atoms. Any one selected from a 50 heterocycloalkyl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms,
R ₂ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon atom having 2 to 30 carbon atoms. Alkenyl group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, substituted or unsubstituted carbon atoms Heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Any one selected from a germanium group, a nitro group, a cyano group, and a halogen group,
Ar ₁ is a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms;
Ar ₂ is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 2 to 50 carbon atoms to 50 heteroaryl groups and substituted or unsubstituted aliphatic aromatic mixed ring groups having 3 to 50 carbon atoms;
l is an integer from 1 to 3, and when l is 2 or more, a plurality of R ₁ are the same as or different from each other;
o and m are integers of 1 or 2, and when o or m is 2 or more, a plurality of A's are the same as or different from each other,
n is an integer of 8, and the plurality of R ₂ are the same as or different from each other;

[Formula 2]

In the above [Formula 2],
X ₁ is B,
Y ₁ and Y ₂ are the same as or different from each other, and are each independently any one selected from NR ₁₁ , O, S, CR ₁₂ R ₁₃ , SiR ₁₄ R ₁₅ and GeR ₁₆ R ₁₇ ;
A ₁ to A ₃ are the same as or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 50 carbon atoms, or a substituted or unsubstituted carbon atom 2 to 50 aromatic heterocycles, substituted or unsubstituted C2-50 aliphatic heterocycles, and substituted or unsubstituted C3-50 aliphatic aromatic mixed rings;
R ₁₁ to R ₁₇ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted An alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted Unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms An aryloxy group, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, and a substituted Or any one selected from an unsubstituted germanium group, a nitro group, a cyano group, and a halogen group,
R ₁₁ to R ₁₇ may be connected to the A ₁ to A ₃ rings to further form an alicyclic or aromatic monocyclic or polycyclic ring;
R ₁₂ and R ₁₃ , R ₁₄ and R ₁₅ , and R ₁₆ and R ₁₇ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,

'Substitution' in 'substituted or unsubstituted' in [Formula 1] and [Formula 2] is deuterium, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, Alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, heterocycloalkyl group having 2 to 24 carbon atoms, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, Alkylaryl group having 7 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 3 to 30 carbon atoms, alkylheteroaryl group having 3 to 30 carbon atoms, aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, and 1 to 30 carbon atoms Alkoxy group of 24, aryloxy group of 6 to 24 carbon atoms, arylthionyl group of 6 to 24 carbon atoms, amine group of 1 to 40 carbon atoms, silyl group of 1 to 40 carbon atoms, germanium group of 1 to 40 carbon atoms, cyano group , It means that it is substituted with one or more substituents selected from the group consisting of a halogen group, a hydroxyl group, and a nitro group, and one or more hydrogens in each substituent can be substituted with deuterium. According to claim 7,
[Formula 2] is an organic light emitting device, characterized in that a polycyclic compound represented by the following [Formula 3] or [Formula 4]:
[Formula 3] [Formula 4]

In [Formula 3] and [Formula 4],
Y ₃ is O, S or NR ₁₈ ;
R ₁₈ is the same as the definition of R ₁₁ to R ₁₇ in [Formula 2] in claim 7, and Y ₁ , Y ₂ and A ₁ to A ₃ are defined in [Formula 2] in claim 7 and same. According to claim 7,
[Formula 2] is an organic light emitting device, characterized in that a polycyclic ring compound represented by any one selected from [Formula 3-1] to [Formula 4-3]:
[Formula 3-1] [Formula 4-1]

In [Formula 3-1] and [Formula 4-1],
Z ₁ to Z ₁₀ are the same as or different from each other, and are each independently CR ₃₁ or N;
Where two or more of Z ₁ to Z ₁₀ are each CR ₃₁ , each CR ₃₁ is the same as or different from each other;
When two or more of Z ₁ to Z ₁₀ are each CR ₃₁ , each adjacent R ₃₁ may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
Y ₃ is O, S or NR ₁₈ ;
R ₁₈ is the same as the definition of R ₁₁ to R ₁₇ in [Formula 2] in claim 7,
R ₃₁ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon atom having 2 to 30 carbon atoms. 30 alkenyl group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, substituted or unsubstituted Heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms Group, 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 amine group, substituted or unsubstituted silyl group, substituted or unsubstituted It is any one selected from a germanium group, a nitro group, a cyano group, and a halogen group,
R ₂₁ to R ₃₀ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, an alkyl group having 1 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an aryl group having 6 to 30 carbon atoms, A cycloalkyl group having 3 to 24 carbon atoms, a heterocycloalkyl group having 2 to 24 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, and a heteroaryl group having 3 to 30 carbon atoms. Alkylaryl group, C3-30 heteroarylalkyl group, C3-30 alkylheteroaryl group, C1-24 alkoxy group, C6-24 aryloxy group, C1-24 alkylthioxy group, carbon number Any one selected from an arylthiooxy group having 5 to 24, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group,
One or more hydrogens in the substituents of R ₂₁ to R ₃₁ may be substituted with deuterium,
Each adjacent substituent among R ₂₁ to R ₃₀ may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
The plurality of R ₃₁ may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
Wherein R ₂₁ , R ₂₅ , R ₂₆ and R ₃₀ are adjacent to each other when Z ₈ and Z ₉ are CR ₃₁ , combined with each of R ₃₁ may further form an alicyclic or aromatic monocyclic or polycyclic ring; ,
Wherein Y ₁ and Y ₂ are the same as or different from each other, and are each independently the same as defined in [Formula 2] in claim 7 or a linking group represented by [Structural Formula A] below,
At least one of Y ₁ and Y ₂ is a linking group represented by [Structural Formula A] below,
[Structural Formula A]

In the above [structural formula A],
R ₄₁ to R ₄₅ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, an alkyl group having 1 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an aryl group having 6 to 30 carbon atoms, A cycloalkyl group having 3 to 24 carbon atoms, a heterocycloalkyl group having 2 to 24 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, and a heteroaryl group having 3 to 30 carbon atoms. Alkylaryl group, C3-30 heteroarylalkyl group, C3-30 alkylheteroaryl group, C1-24 alkoxy group, C6-24 aryloxy group, C1-24 alkylthioxy group, carbon number Any one selected from an arylthiooxy group having 5 to 24, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group,
One or more hydrogens in the substituents of R ₄₁ to R ₄₅ may be substituted with deuterium,
R ₄₁ to R ₄₅ may be linked to adjacent substituents to further form an alicyclic or aromatic monocyclic or polycyclic ring;

[Formula 3-2] [Formula 4-2]

In [Formula 3-2] and [Formula 4-2],
Z ₁ to Z ₁₀ are the same as or different from each other, and are each independently CR ₃₁ or N;
Where two or more of Z ₁ to Z ₁₀ are each CR ₃₁ , each CR ₃₁ is the same as or different from each other;
When two or more of Z ₁ to Z ₈ are each CR ₃₁ , each adjacent R ₃₁ may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
Y ₃ is O, S or NR ₁₈ ;
R ₁₈ is the same as the definition of R ₁₁ to R ₁₇ in [Formula 2] in claim 7,
M is Si or Ge;
R ₃₁ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon atom having 2 to 30 carbon atoms. Alkenyl group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, substituted or unsubstituted carbon atoms Heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted It is any one selected from a germanium group, a nitro group, a cyano group, and a halogen group,
R ₄₆ to R ₄₈ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, or a substituted or unsubstituted carbon atom. Alkenyl group having 2 to 24 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 24 carbon atoms, substituted or unsubstituted Cyclic heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 24 carbon atoms, substituted or unsubstituted C6 to 24 carbon atoms An aryloxy group, a substituted or unsubstituted alkylthio group having 1 to 24 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 24 carbon atoms, a substituted or unsubstituted amine group having 1 to 30 carbon atoms, a substituted or unsubstituted 1 Any one selected from a silyl group of 1 to 30, a substituted or unsubstituted germanium group of 1 to 30, a nitro group, a cyano group, and a halogen group,
One or more hydrogens in the substituents of R ₃₁ and R ₄₆ to R ₄₈ may be substituted with deuterium,
Each of the substituents of R ₄₆ to R ₄₈ may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring;

[Formula 3-3] [Formula 4-3]

In [Formula 3-3] and [Formula 4-3],
Z ₁ to Z ₁₁ are the same as or different from each other, and are each independently CR ₃₁ or N,
Where two or more of Z ₁ to Z ₁₁ are each CR ₃₁ , each CR ₃₁ is the same as or different from each other;
When two or more of Z ₁ to Z ₁₁ are each CR ₃₁ , each adjacent R ₃₁ may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
Y ₃ is O, S or NR ₁₈ ;
R ₁₈ is the same as the definition of R ₁₁ to R ₁₇ in [Formula 2] in claim 7,
R ₃₁ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon atom having 2 to 30 carbon atoms. Alkenyl group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, substituted or unsubstituted carbon atoms Heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted It is any one selected from a germanium group, a nitro group, a cyano group, and a halogen group, wherein at least one hydrogen in the substituent of R ₃₁ can be substituted with deuterium,
Wherein Y ₁ and Y ₂ are the same as or different from each other, and are each independently the same as defined in [Formula 2] in claim 7 or a linking group represented by [Structural Formula B] below,
At least one of Y ₁ and Y ₂ is a linking group represented by [Structural Formula B] below,
[Structural Formula B]

In the above [structural formula B],
X ₂ is O or S;
R ₅₁ to R ₅₈ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, an alkyl group having 1 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an aryl group having 6 to 30 carbon atoms, A cycloalkyl group having 3 to 24 carbon atoms, a heterocycloalkyl group having 2 to 24 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, and a heteroaryl group having 3 to 30 carbon atoms. Alkylaryl group, C3-30 heteroarylalkyl group, C3-30 alkylheteroaryl group, C1-24 alkoxy group, C6-24 aryloxy group, C1-24 alkylthioxy group, carbon number Any one selected from an arylthiooxy group having 5 to 24, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group,
One or more hydrogens in the substituents of R ₅₁ to R ₅₈ may be substituted with deuterium,
Any one of R ₅₁ to R ₅₈ is a single bond bonded to the nitrogen atom, and the remaining R ₅₁ to R ₅₈ excluding the single bond are linked to adjacent substituents to form an alicyclic or aromatic monocyclic or polycyclic ring. can,
'Substitution' in 'substituted or unsubstituted' in [Formula 3-1] to [Formula 4-3] refers to heavy hydrogen, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, and a carbon atom having 3 to 24 carbon atoms. Cycloalkyl group, C2-24 alkenyl group, C2-24 alkynyl group, C1-24 heteroalkyl group, C2-24 heterocycloalkyl group, C6-30 aryl group, C7-30 Arylalkyl group, C7-30 alkylaryl group, C2-30 heteroaryl group, C3-30 heteroarylalkyl group, C3-30 alkylheteroaryl group, C3-30 aliphatic aromatic mixed ring group , C1-24 alkoxy group, C6-24 aryloxy group, C6-24 arylthionyl group, C1-40 amine group, C1-40 silyl group, C1-40 low ma It means that it is substituted with one or more substituents selected from the group consisting of a nium group, a cyano group, a halogen group, a hydroxyl group, and a nitro group, and one or more hydrogens in each substituent can be substituted with deuterium. According to claim 7,
An organic light emitting device, characterized in that the polycyclic ring compound represented by [Formula 2] is any one selected from the following compounds:

According to claim 7,
The organic layer is a hole injection layer, a hole transport layer, an electron blocking layer, a functional layer having a hole injection function and a hole transport function at the same time, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, having an electron injection function and an electron transport function at the same time An organic light emitting device comprising at least one layer among functional layers. According to claim 11,
At least one layer selected from the respective layers is an organic light emitting device formed by a deposition process or a solution process. According to claim 7,
An organic light emitting device, characterized in that the host of the light emitting layer is used by mixing or stacking one or more compounds in addition to one anthracene derivative compound represented by [Formula 1]. According to claim 7,
An organic light emitting device, characterized in that the dopant in the light emitting layer is used by mixing or stacking one or more compounds in addition to one polycyclic compound represented by [Chemical Formula 2]. According to claim 7,
The organic light emitting diode may include a flat panel display device; flexible display devices; devices for monochromatic or white flat lighting; devices for flexible lighting in monochromatic or white; vehicle display devices; And a display device for virtual or augmented reality; organic light emitting device used in any one device selected from.