KR20230150230A - Organic light-emitting device - Google Patents

Abstract

The present invention relates to a high-efficiency, long-life organic light-emitting device with significantly improved lifespan and luminous efficiency by employing an anthracene derivative compound with a characteristic structure and a polycyclic ring derivative with a characteristic structure in a light-emitting layer.

Description

Organic light-emitting device {Organic light-emitting device}

The present invention relates to a high-efficiency, long-life organic light-emitting device in which lifespan and external quantum efficiency are significantly improved by employing an anthracene derivative compound and a polycyclic ring compound having a characteristic structure as a light-emitting layer host and dopant material, respectively.

In an organic light emitting device, electrons injected from an electron injection electrode (cathode electrode) and holes injected from a hole injection electrode (anode electrode) combine in the light emitting layer to form an exciton, and the exciton produces energy. It is a self-luminous device that emits light while emitting light, and such organic light-emitting devices are attracting attention as next-generation light sources due to the advantages of low driving voltage, high luminance, wide viewing angle, fast response speed, and applicability to full-color flat panel light-emitting displays. .

In order for these organic light-emitting devices to exhibit the above characteristics, the structure of the organic layer within the device must be optimized, and the materials that make up each organic layer: hole injection material, hole transport material, light-emitting material, electron transport material, electron injection material, and electron blocking material. Although these must be supported by stable and efficient materials, there is still a need for the development of stable and efficient organic layer structures and materials for organic light-emitting devices.

In particular, in order to obtain maximum efficiency in the light emitting layer, the energy band gap of the host and the dopant must be appropriately combined so that holes and electrons can each move to the dopant through a stable electrochemical path to form excitons.

Therefore, the present invention seeks to provide a high-efficiency, long-life organic light-emitting device with significantly improved lifespan and luminous efficiency by employing a combination of characteristic host materials and dopant materials used as hosts in the light-emitting layer in the organic light-emitting device.

In order to solve the above problems, the present invention provides an organic light-emitting device including a light-emitting layer employing a combination of characteristic host materials and dopant materials, and the light-emitting layer is composed of a plurality of hosts and a dopant. Provides an organic light-emitting device containing

According to one embodiment of the present invention, a first electrode; and a second electrode facing the first electrode; a first light emitting layer including a first host and a first dopant between the first electrode and the second electrode; and a second light emitting layer including a second host and a second dopant sequentially, wherein at least one of the first host and the second host is an anthracene compound represented by the following [Formula 1] or [Formula 2]. An organic light-emitting device comprising one or more types is provided.

[Formula 1] [Formula 2]

The characteristic structure of [Formula 1] or [Formula 2], specific compounds implemented thereby, and definitions of each substituent will be described later.

In addition, according to an embodiment of the present invention, one of the first host and the second host includes one or more anthracene compounds represented by [Formula 1] or [Formula 2], and the first host and the second host The remaining one of the hosts may include one or more anthracene compounds represented by the following [Formula 5].

[Formula 5]

The characteristic structure of [Formula 5], the specific compounds realized thereby, and the definition of each substituent will be described later.

Additionally, according to an embodiment of the present invention, a first electrode; and a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode. The organic layer includes a light-emitting layer, and the light-emitting layer includes a host and a dopant. ;, the host includes at least one anthracene compound represented by the following [Formula 1] or [Formula 2], and the dopant is a polycyclic ring compound represented by the following [Formula 3] or [Formula 4] Provided is an organic light emitting device comprising at least one type of.

[Formula 1] [Formula 2]

[Formula 3] [Formula 4]

The characteristic structures of [Formula 1], [Formula 2], [Formula 3], and [Formula 4], specific compounds implemented thereby, and definitions of each substituent will be described later.

The present invention can implement a significantly improved high-efficiency, long-life organic light-emitting device by employing an anthracene derivative compound and a polycyclic ring compound with a characteristic structure in the light-emitting layer, making it useful for various display devices such as flat panel, flexible, and wearable displays as well as lighting devices. You can utilize it.

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

One aspect of the present invention is a first electrode; and a second electrode facing the first electrode; a first light emitting layer including a first host and a first dopant between the first electrode and the second electrode; and a second light-emitting layer including a second host and a second dopant, wherein at least one of the first host and the second host has the following [Formula 1] or [Formula 2]. It is characterized in that it contains one or more types of anthracene compounds represented by ].

[Formula 1] [Formula 2]

The anthracene derivative compound represented by [Formula 1] or [Formula 2] is structurally (i) an aryl group or heteroaryl group introduced at the 9th position of the anthracene, and (ii) Ar at a specific position at the 10th position of the anthracene. It is characterized by a structure in which dibenzofuran (thiophene) having ₁ and Ar ₂ (aryl group or heteroaryl group) and R (hydrogen or deuterium) as substituents is introduced.

In [Formula 1] to [Formula 2],

R is hydrogen or deuterium.

R ₁ to R ₉ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group with 2 to 30 carbon atoms, and a substituted or unsubstituted carbon number. Alkenyl group of 2 to 30 carbon atoms, substituted or unsubstituted aryl group of 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted Ringed heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms Aryloxy 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 It is selected from unsubstituted germanium group, nitro group, cyano group and halogen group.

Ar ₁ to Ar ₃ are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms. It is selected from 30 aliphatic aromatic mixed ring groups.

X is O or S.

L is a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms.

n is an integer of 1 to 3, and when n is an integer of 2 or more, the plurality of Ls are the same or different from each other.

m is an integer of 4, and each of the plurality of R ₉ is the same as or different from each other.

The plurality of R ₉ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring is selected from N, S and O. It may be substituted with one or more heteroatoms.

'Substitution' in 'substituted or unsubstituted' in [Formula 1] and [Formula 2] means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, halogenation with 1 to 24 carbon atoms. alkyl group, cycloalkyl group with 3 to 30 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, arylalkyl group with 7 to 24 carbon atoms , alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 2 to 24 carbon atoms, aliphatic aromatic mixed ring group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, and 1 to 2 carbon atoms. Substituted with one or more substituents selected from the group consisting of an amine group of 24, a silyl group of 1 to 24 carbon atoms, a germanium group of 1 to 24 carbon atoms, an aryloxy group of 6 to 24 carbon atoms, and an arylthionyl group of 6 to 24 carbon atoms. This means that, in two or more cases, they are the same or different from each other, and one or more hydrogens in each substituent can be replaced with deuterium.

According to one embodiment of the present invention, the [Formula 1] may be represented by any one selected from the following [Formula 1-1] to [Formula 1-5].

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

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

[Formula 1-5]

In [Formula 1-1] to [Formula 1-5],

X ₁ is any one selected from O, S and CR ₁₁ R ₁₂ .

R ₁₀ is each independently hydrogen, deuterium, a deuterium-substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a deuterium-substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, and a deuterium-substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms It is selected from aliphatic aromatic mixed ring groups.

R ₁₁ and R ₁₂ are the same as or different from each other, and are each independently a deuterium-substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

p is an integer of 5, q is an integer of 7, r is an integer of 9, s is an integer of 9, t is an integer of 7, and the plurality of R ₁₀ are the same or different from each other.

The plurality of R ₁₀ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

R ₁₁ and R ₁₂ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

The carbon atoms of the alicyclic, aromatic, monocyclic or polycyclic ring formed above may be substituted with any one or more heteroatoms selected from N, S and O.

X, n, m, L, Ar ₁ , Ar ₂ , R and R ₁ to R ₉ are the same as defined in [Formula 1] above.

According to one embodiment of the present invention, the [Formula 2] may be represented by any one selected from the following [Formula 2-1] to [Formula 2-5].

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

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

[Formula 2-5]

In [Formula 2-1] to [Formula 2-5],

X ₁ is any one selected from O, S and CR ₁₁ R ₁₂ .

R ₁₀ is each independently hydrogen, deuterium, a deuterium-substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a deuterium-substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, and a deuterium-substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms It is selected from aliphatic aromatic mixed ring groups.

R ₁₁ and R ₁₂ are the same as or different from each other, and are each independently a deuterium-substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

p is an integer of 5, q is an integer of 7, r is an integer of 9, s is an integer of 9, t is an integer of 7, and the plurality of R ₁₀ are the same or different from each other.

The plurality of R ₁₀ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

R ₁₁ and R ₁₂ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

The carbon atoms of the alicyclic, aromatic, monocyclic or polycyclic ring formed above may be substituted with any one or more heteroatoms selected from N, S and O.

X, n, m, L, Ar ₁ , Ar ₂ , R and R ₁ to R ₉ are the same as defined in [Formula 2] above.

According to one embodiment of the present invention, L in [Formula 1] and [Formula 2] may be any one selected from the following [Structural Formula 1] to [Structural Formula 5].

[Structural Formula 1] [Structural Formula 2] [Structural Formula 3]

[Structural Formula 4] [Structural Formula 5]

According to an embodiment of the present invention, one of the first host and the second host includes one or more anthracene compounds represented by [Formula 1] or [Formula 2], and among the first host and the second host, The remaining one may include one or more anthracene compounds represented by the following [Chemical Formula 5].

[Formula 5]

In [Formula 5] above,

X ₂ is O or S.

Ar ₄ is selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, 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 ₅₁ to R ₆₆ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group with 2 to 30 carbon atoms, or a substituted or unsubstituted carbon number. Alkenyl group of 2 to 30 carbon atoms, substituted or unsubstituted aryl group of 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted Ringed heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms Aryloxy 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 It is selected from unsubstituted germanium group, nitro group, cyano group and halogen group.

L ₁ is a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms.

o is an integer from 1 to 3, and when o is 2 or more, a plurality of L _1s are the same or different from each other.

Each of the adjacent R ₅₉ to R ₆₆ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring are N, S and It may be substituted with any one or more heteroatoms selected from O.

According to one embodiment of the present invention, at least four of R ₁ to R ₈ in [Formula 1] or [Formula 2] are deuterium, and at least four of R ₅₁ to R ₅₈ in [Formula 5] are deuterium. It is characterized by being.

In the above [Formula 5], 'substituted' in 'substituted or unsubstituted' means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, halogenated alkyl group with 1 to 24 carbon atoms, and 3 carbon atoms. Cycloalkyl group of 30 to 30 carbon atoms, alkenyl group of 2 to 24 carbon atoms, alkynyl group of 2 to 24 carbon atoms, heteroalkyl group of 1 to 24 carbon atoms, aryl group of 6 to 24 carbon atoms, arylalkyl group of 7 to 24 carbon atoms, 7 to 24 carbon atoms alkylaryl group, heteroaryl group with 2 to 24 carbon atoms, heteroarylalkyl group with 2 to 24 carbon atoms, aliphatic aromatic mixed ring group with 3 to 24 carbon atoms, alkoxy group with 1 to 24 carbon atoms, amine group with 1 to 24 carbon atoms, It means being substituted with one or more substituents selected from the group consisting of a silyl group with 1 to 24 carbon atoms, a germanium group with 1 to 24 carbon atoms, an aryloxy group with 6 to 24 carbon atoms, and an arylthionyl group with 6 to 24 carbon atoms, and two or more In these cases, they are the same or different from each other, and one or more hydrogens in each substituent can be replaced with deuterium.

Another aspect of the present invention includes a first electrode, a second electrode opposite the first electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer, and the light-emitting layer It relates to an organic light emitting device comprising a host and a dopant, wherein the host includes at least one anthracene compound represented by the following [Formula 1] or [Formula 2], and the dopant has the following [Formula 3] or [ It is characterized by containing at least one polycyclic ring compound represented by the formula (4).

[Formula 1] [Formula 2]

In [Formula 1] to [Formula 2],

R is hydrogen or deuterium.

R ₁ to R ₉ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group with 2 to 30 carbon atoms, and a substituted or unsubstituted carbon number. Alkenyl group of 2 to 30 carbon atoms, substituted or unsubstituted aryl group of 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted Ringed heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms Aryloxy 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 It is selected from unsubstituted germanium group, nitro group, cyano group and halogen group.

Ar ₁ to Ar ₃ are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms. It is any one selected from 30 aliphatic aromatic mixed ring groups.

X is O or S.

L is a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms.

n is an integer of 1 to 3, and when n is an integer of 2 or more, the plurality of Ls are the same or different from each other.

m is an integer of 4, and each of the plurality of R ₉ is the same as or different from each other.

The plurality of R ₉ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[Formula 3] [Formula 4]

In [Formula 3] and [Formula 4],

Y ₃ is O or S.

Y ₁ and Y ₂ are the same as or different from each other, and are each independently NR ₁₄ , O, S, CR ₁₅ R ₁₆ , SiR ₁₇ R ₁₈ or GeR ₁₉ R ₂₀ .

A ₁ to A ₃ are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 3 to 50 carbon atoms. It is any one selected from an aliphatic ring having 3 to 30 carbon atoms and a substituted or unsubstituted aliphatic aromatic mixed ring having 3 to 30 carbon atoms.

R ₁₄ to R ₂₀ are the same or different from each other, and each independently represents hydrogen, deuterium, 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 alkynyl group. Alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group with 3 to 30 carbon atoms, substituted or Unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted carbon number 6 to 30 Aryloxy 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 any one selected from unsubstituted germanium group, nitro group, cyano group, and halogen group.

R ₁₄ to R ₂₀ may be connected to the A ₁ to A ₃ rings to further form an alicyclic or aromatic monocyclic or polycyclic ring.

R ₁₅ and R ₁₆ , R ₁₇ and R ₁₈ , and R ₁₉ and R ₂₀ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

The carbon atoms of the alicyclic, aromatic, monocyclic or polycyclic ring formed above may be substituted with any one or more heteroatoms selected from N, S and O.

'Substitution' in 'substituted or unsubstituted' in [Formula 1] to [Formula 4] means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, halogenation with 1 to 24 carbon atoms. alkyl group, cycloalkyl group with 3 to 30 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, arylalkyl group with 7 to 24 carbon atoms , alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 2 to 24 carbon atoms, aliphatic aromatic mixed ring group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, and 1 to 2 carbon atoms. Substituted with one or more substituents selected from the group consisting of an amine group of 24, a silyl group of 1 to 24 carbon atoms, a germanium group of 1 to 24 carbon atoms, an aryloxy group of 6 to 24 carbon atoms, and an arylthionyl group of 6 to 24 carbon atoms. This means that, in two or more cases, they are the same or different from each other, and one or more hydrogens in each substituent can be replaced with deuterium.

According to one embodiment of the present invention, the [Formula 3] is represented by the following [Formula 3-1] to [Formula 3-3], and [Formula 4] is represented by the following [Formula 4-1] to [Formula 4- 3].

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

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

The definitions of Y ₁ to Y ₃ are the same as those defined in [Formula 3] and [Formula 4] above.

Z ₁ to Z ₁₀ are the same as or different from each other, and are each independently CR ₃₁ or N.

When two or more of Z ₁ to Z ₁₀ are each CR ₃₁ , each R ₃₁ is the same or different from each other.

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

R ₂₁ to R ₃₁ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group with 2 to 30 carbon atoms, or a substituted or unsubstituted carbon number. Alkenyl group of 2 to 30 carbon atoms, substituted or unsubstituted aryl group of 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted Ringed heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms Aryloxy 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 It is any one selected from unsubstituted germanium group, nitro group, cyano group and halogen group.

Substituents adjacent to each other among R ₂₁ to R ₃₀ may be connected to each other to further form an alicyclic or aromatic mono- or polycyclic ring.

When Z ₈ and Z ₉ are CR 31, R ₂₁ , R ₂₅ , R ₂₆ and R ₃₀ may be combined with each R ₃₁ to form _an additional alicyclic or aromatic mono- or polycyclic ring.

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 ₃₂ to R ₃₆ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group with 2 to 30 carbon atoms, and a substituted or unsubstituted carbon number. Alkenyl group of 2 to 30 carbon atoms, substituted or unsubstituted aryl group of 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group of 3 to 30 carbon atoms, substituted or unsubstituted Ringed heterocycloalkyl group having 1 to 30 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 carbon number 1 to 30 alkoxy group, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, substituted or unsubstituted It is selected from an amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group.

Adjacent substituents of R ₃₂ to R ₃₆ may be connected to form an additional alicyclic or aromatic monocyclic or polycyclic ring.

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

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

The definitions of Y ₁ to Y ₃ are the same as those defined in [Formula 3] and [Formula 4] above.

Z ₁ to Z ₁₀ are the same as or different from each other, and are each independently CR ₃₁ or N.

When two or more of Z ₁ to Z ₁₀ are each CR ₃₁ , each R ₃₁ is the same or different from each other.

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

M is Si or Ge.

R ₃₁ and R ₃₇ to R ₃₉ are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, substituted or unsubstituted A substituted or unsubstituted 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 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, Substituted or unsubstituted heterocycloalkyl group having 1 to 30 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 carbon atoms Alkoxy group of 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group of 6 to 30 carbon atoms, substituted or unsubstituted alkylthoxy group of 1 to 30 carbon atoms, substituted or unsubstituted arylthoxy group of 5 to 30 carbon atoms, substituted or an unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group.

R ₃₇ to R ₃₉ 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 are each independently CR ₃₁ or N.

When two or more of Z ₁ to Z ₁₁ are each CR ₃₁ , each R ₃₁ is the same or different from each other.

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

The definitions of Y ₁ to Y ₃ are the same as those defined in [Formula 3] and [Formula 4] above, except that at least one of Y ₁ and Y ₂ is a linking group represented by [Structural Formula B] below.

[Structural Formula B]

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

X ₂ is O or S.

R ₃₁ and R ₄₁ to R ₄₈ are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, substituted or unsubstituted A substituted or unsubstituted 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 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 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 carbon number 6 Aryloxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, substituted or unsubstituted amine group, substituted or unsubstituted silyl group , substituted or unsubstituted germanium group, nitro group, cyano group and halogen group.

Any one of R ₄₁ to R ₄₈ is bonded to Y ₁ or Y ₂ by a single bond with a nitrogen atom, and R ₄₁ to R ₄₈ excluding this is bonded to each other or adjacent substituents to form an alicyclic or aromatic single ring. Alternatively, it may form a polycyclic ring.

The carbon atoms of the additionally formed alicyclic, aromatic, monocyclic or polycyclic rings in [Formula 3-1] to [Formula 4-3] may be substituted with any one or more heteroatoms selected from N, S and O.

'Substitution' in 'substituted or unsubstituted' in [Formula 3-1] to [Formula 4-3] means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, and 1 carbon atom. Halogenated alkyl group of 2 to 24 carbon atoms, cycloalkyl group of 3 to 30 carbon atoms, alkenyl group of 2 to 24 carbon atoms, alkynyl group of 2 to 24 carbon atoms, heteroalkyl group of 1 to 24 carbon atoms, aryl group of 6 to 30 carbon atoms, and 7 to 7 carbon atoms. Arylalkyl group of 30, alkylaryl group of 7 to 30 carbon atoms, heteroaryl group of 2 to 30 carbon atoms, heteroarylalkyl group of 2 to 24 carbon atoms, aliphatic aromatic mixed ring group of 3 to 30 carbon atoms, alkoxy group of 1 to 24 carbon atoms , 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, an aryloxy group having 6 to 24 carbon atoms, and an arylthionyl group having 6 to 24 carbon atoms. It means being substituted with, and in the case of two or more, they are the same or different from each other, and one or more hydrogens in each substituent can be replaced with deuterium.

Meanwhile, in the present invention, forming a ring by combining with adjacent groups means that a substituted or unsubstituted alicyclic or aromatic ring can be formed by combining with adjacent groups, and 'adjacent substituent' refers to the The substituent may mean a substituent substituted on an atom directly connected to the substituted atom, a substituent sterically located closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring can be interpreted as 'adjacent substituents'.

In the present invention, the alkyl group may be straight chain or branched, and specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, 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 arylalkyl groups include, but are not limited to, phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl, and naphthylethyl.

In the present invention, specific examples of alkylaryl groups 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 vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl 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 are not limited to these.

In the present invention, the alkynyl group also includes a straight chain or branched chain and may be further substituted by other substituents, and examples include, but are limited to, ethynyl, 2-propynyl, etc. 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 but is not an aromatic ring, and includes cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, 1, Examples include, but are not limited to, 3-cyclohexadienyl group, 1,4-cyclohexadienyl group, 2,4-cycloheptadienyl group, and 1,5-cyclooctadienyl group.

In the present invention, the aromatic hydrocarbon ring or aryl group may be monocyclic or polycyclic. Examples of the monocyclic aryl group include phenyl group, biphenyl group, terphenyl group, and stilbene group, and examples of the polycyclic aryl group include a naphthyl group. , anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group, chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthene group, etc., but the scope of the present invention is It is not limited to these examples.

In the present invention, the aromatic heterocycle or heteroaryl group is an aromatic ring containing one or more heteroatoms, examples of which include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, and oxadia. 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, benzooxazole 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, phenothiazinyl group, etc. However, it is not limited to these.

In the present invention, an aliphatic hydrocarbon ring or cycloalkyl group refers to a non-aromatic ring consisting only of carbon and hydrogen atoms, examples of which include monocyclic or polycyclic, and may be further substituted by other substituents. A ring refers to a group directly connected or condensed with another ring group. 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 aryl group, or a heteroaryl group. 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, and cyclooctyl group, and cyclohexane and cyclo It includes, but is not limited to, cycloalkanes such as pentane, and cyclocycloalkenes such as cyclohexene and cyclobutene.

In the present invention, an aliphatic heterocycle or heterocycloalkyl group refers to an aliphatic ring containing one or more heteroatoms, and includes heteroatoms such as O, S, Se, N or Si, and is also monocyclic or polycyclic. and may be further substituted by other substituents. Polycyclic refers to a group in which heterocycloalkyl, heterocycloalkane, heterocycloalgen, etc. are directly connected or condensed with another ring group, and other ring groups are aliphatic hetero. It may be a ring, but it may also be another type of ring group, such as an aliphatic hydrocarbon ring, an aryl group, or a heteroaryl group.

In the present invention, an aliphatic aromatic mixed ring (group) refers to a ring in which two or more rings are connected and condensed, and the aliphatic ring and the aromatic ring are condensed to have overall non-aromaticity. More specifically, is an aromatic hydrocarbon ring (group) condensed with an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring (group) condensed with an aliphatic heterocycle, an aromatic heterocycle (group) condensed with an aliphatic hydrocarbon ring, an aromatic heterocycle (group) condensed with an aliphatic heterocycle, aromatic It may be an aliphatic hydrocarbon ring (group) condensed with a hydrocarbon ring, an aliphatic hydrocarbon ring (group) condensed with an aromatic hetero ring, an aliphatic hetero ring (group) condensed with an aromatic hydrocarbon ring, an aliphatic hetero ring (group) condensed with an aromatic hetero ring, etc., Specific examples include tetrahydronaphthyl group, tetrahydrobenzocycloheptene, tetrahydrophenanthrene group, tetrahydroanthracenyl group, octahydrotriphenylene group, tetrahydrobenzothiophene group, tetrahydrobenzofuranyl group, tetrahydrocarbazole group, Tetrahydroquinoline group, etc. In addition, in the aliphatic aromatic mixed ring (group), in addition to carbon, heteroatoms such as N, NR, O, S, Si, Ge, etc. can be replaced, and R is the same as the definition of R ₁ and R ₂ in [Formula 1].

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

In the present invention, the silyl group may include -SiH ₃ , alkylsilyl group, arylsilyl group, alkylarylsilyl group, arylheteroarylsilyl group, heteroarylsilyl group, etc., and the arylsilyl group is -SiH ₃ It refers to a silyl group in which one, two, or three hydrogens are substituted with an aryl group, and an alkylsilyl group refers to an amine in which one, two, or three hydrogens are substituted with alkyl in SiH ₃ , and an alkylarylsilyl group is - In SiH ₃ , at least one hydrogen is replaced by an alkyl group and an aryl group, respectively, meaning a silyl group containing 1 or 2 alkyl groups and 2 or 1 aryl groups corresponding thereto, and the arylheteroarylsilyl group is -SiH ₃ In this case, at least one hydrogen is replaced with an aryl group and a heteroaryl group, respectively, meaning a silyl group containing 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, two, or three hydrogens are substituted with a heteroaryl group. 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 heteroarylsilyl group.

Here, each aryl group in the arylsilyl group, heteroarylsilyl group, and arylheteroarylsilyl group may be a monocyclic aryl group or a polycyclic aryl group, and the arylsilyl group, heteroarylsilyl group, and arylheteroarylsilyl group may be a monocyclic aryl group or a polycyclic aryl group. Each heteroaryl group 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, etc. One or more hydrogen atoms of the silyl group may be replaced with the same substituent as that 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, etc., and the arylamine group is -NH ₂ It refers to an amine in which one or two hydrogens are substituted with an aryl group, and an alkylamine group refers to an amine in which one or two hydrogens are substituted with alkyl in -NH ₂ , and an alkylarylamine group in -NH ₂ One hydrogen refers to an amine in which one hydrogen is an alkyl group and the other hydrogen is substituted in an aryl group. In -NH ₂ , an arylheteroarylamine group refers to 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 refers to an amine in which one or two hydrogens in -NH ₂ are substituted with a heteroaryl group. Examples of the arylamine group include substituted or unsubstituted monoarylamine group, substituted or unsubstituted monoarylamine group. There is a substituted diarylamine group, or a substituted or unsubstituted triarylamine group, and the same applies to the alkylamine group and heteroarylamine group.

Here, each aryl group in the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic aryl group or a polycyclic aryl group, and the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic aryl group or a polycyclic aryl group. Each heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. Or it may be a polycyclic aryl group, and each heteroaryl group 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 alkylaryl germanium group, an alkylheteroaryl germanium group, an arylheteroaryl germanium group, etc. These definitions follow those described for the silyl group, but can be applied to each substituent as a substituent obtained by substituting a germanium atom (Ge) in place of a silicon atom (Si) in the silyl group.

In addition, specific examples of the germanium group include trimethylgermain, triethylgermain, triphenylgermain, trimethoxygermain, dimethoxyphenylgermain, diphenylmethylgermain, diphenylvinylgermain, methylcyclobutylgermain, dimethylfurylgermain, etc. One or more hydrogen atoms of the germanium group can be replaced with the same substituent as that of the aryl group.

In the present invention, the cycloaryl group, aryl group, and heteroaryl group among the cycloalkyloxy group, aryloxy group, heteroaryloxy group, cycloalkylthio group, arylthio group, and heteroarylthio group include the above-mentioned cycloaryl group and aryl group. It is the same as the example of heteroaryl group, and specific examples of aryloxy groups include phenoxy group, p-toryloxy group, m-toryloxy 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. The arylthioxy group includes, but is not limited to, phenylthioxy group, 2-methylphenylthioxy group, and 4-tert-butylphenylthioxy group.

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

According to one embodiment of the present invention, the anthracene compound represented by [Formula 1] or [Formula 2] may be any one selected from compounds represented by the following formula, but the scope is not limited thereto. .

In addition, according to one embodiment of the present invention, [Formula 3] or [Formula 4] may be any one selected from compounds represented by the following formula, but the scope is not limited thereto.

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, etc. However, it is not limited to this and may include a smaller number or a larger number of organic layers, and the structure of the organic material layer of the preferred organic light emitting device according to the present invention will be described in more detail in the examples described later.

Hereinafter, an embodiment of an 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. If necessary, it may further include a hole injection layer between the anode and the hole transport layer, and an electron transport layer between the electron transport layer and the cathode. It may further include an injection layer, and in addition, it is possible to further form an intermediate layer of one or two layers, and a hole blocking layer or an electron blocking layer may be further formed, and as described above, a capping layer, etc. of the device may be formed. Depending on the characteristics, it may further include an organic layer having various functions.

In addition, each organic layer, including the light-emitting layer, may be composed of multiple layers, and according to an embodiment of the present invention, the light-emitting layer is composed of a plurality of layers, and the host material and dopant material used therein are stacked or mixed in a plurality. You may.

Meanwhile, the specific structure of the organic light-emitting device according to an embodiment of the present invention, its manufacturing method, and each organic layer material are as follows.

First, an anode is formed by coating the anode electrode material on the top of the substrate. Here, the substrate used in conventional organic light-emitting devices is used, and an organic substrate or a transparent plastic substrate with excellent transparency, surface smoothness, ease of handling, and waterproofing is preferred. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), and zinc oxide (ZnO), which are transparent and have excellent conductivity, are used as materials for the anode electrode.

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 material is vacuum thermal evaporation or spin coating on top of the hole injection layer to form a hole transport layer. .

The hole injection layer material can be used without particular limitation as long as it is commonly used in the industry, 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) can be used.

Subsequently, a hole auxiliary layer and a light-emitting layer can be successively stacked on top of the hole transport layer, and a hole-blocking layer can be selectively formed on top of the light-emitting layer by vacuum deposition or spin coating. The hole blocking layer serves to prevent this problem by using a material with 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 must have an electron transport ability and a higher ionization potential than the light-emitting compound. Representative examples include BAlq, BCP, and TPBI.

Materials used in the hole blocking layer include BAlq, BCP, Bphen, TPBI, TAZ, BeBq ₂ , OXD-7, Liq, etc., but are not limited thereto.

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

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

As the electron transport layer material, which functions to stably transport electrons injected from the cathode, a known electron transport material can be used. Examples of known electron transport substances include quinoline derivatives, especially tris(8-quinolinolate)aluminum(Alq3), TAZ, BAlq, beryllium bis(benzoquinolin-10- Materials such as 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, where the deposition method evaporates the material used to form each layer through heating in a vacuum or low pressure state. It refers to a method of forming a thin film, and the solution process involves mixing the materials used to form each layer with a solvent and performing inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, and spin coating. It refers to a method of forming a thin film through methods such as the above.

In addition, the organic light emitting device according to the present invention is used in devices selected from the group consisting of flat panel display devices, flexible display devices, monochromatic or white flat lighting devices, monochromatic or white flexible lighting devices, vehicle display devices, and virtual or augmented reality display devices. can be used

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

Synthesis Example 1. Synthesis of [BH-1]

Synthesis Example 1-1: Synthesis of A-1

<A-1>

In a 2 L round bottom flask, 84 g of 2-aminodibenzofuran was dissolved in 600 mL of N,N-dimethylformamide and stirred at room temperature. 163.2 g of N-bromosuccinimide was dissolved in 250 mL of N,N-dimethylformamide and added dropwise to the reaction solution. After stirring at the same temperature for 1 hour, completion of the reaction was confirmed by thin layer chromatography, and the reaction solution was poured into a beaker containing 2 L of water and stirred. The produced solid was washed with water and methanol, and the solid was separated and purified by column chromatography, and then recrystallized with dichloromethane and heptane to obtain <A-1>. (140 g, 89.6%)

Synthesis Example 1-2: Synthesis of A-2

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

Add 140 g of <A-1>, 120.1 g of <A-2a>, 18.98 g of tetrakis(triphenylphosphine)palladium, and 120.89 g of potassium carbonate into a 5 L round bottom flask, 980 mL of toluene, 420 mL of ethanol, and water. 280 mL was added. The temperature of the reactor was raised and refluxed and stirred overnight. When the reaction was completed, the temperature of the reactor was lowered to room temperature, the organic layer was separated, and concentrated under reduced pressure. The material was separated and purified by column chromatography to obtain <A-2>. (115 g, 83.5%)

Synthesis Example 1-3: Synthesis of A-3

<A-2> <A-3>

115 g of <A-2>, 195.44 g of para-toluenesulfonic acid, and 1200 mL of acetonitrile were added to a 5L round bottom flask and stirred at room temperature for 10 minutes. The temperature of the reactor was cooled and 47.32 g of sodium nitrite aqueous solution was slowly added dropwise at -10°C and stirred at the same temperature for 30 minutes. 142.29 g of potassium iodide aqueous solution was slowly added dropwise and stirred at room temperature. After completion of the reaction, extraction was performed with dichloromethane and water, and the organic layer was washed several times with an aqueous sodium thiosulfate solution. The organic layer was concentrated under reduced pressure and purified by column chromatography to obtain <A-3>. (120 g, 78.4%)

Synthesis Example 1-4: Synthesis of A-4

<A-3> <A-4>

110 g of <A-3> and 900 mL of tetrahydrofuran were dissolved in a 3L round bottom flask and cooled to -78°C under a nitrogen atmosphere. 118.3 mL of n-butyllithium (2.5M) was slowly added dropwise to the cooled reaction solution and stirred at the same temperature for 1 hour. Then, 30.73 g of trimethylborate was slowly added dropwise and stirred at room temperature. After completion of the reaction, dinormal hydrochloric acid was added dropwise to acidify the mixture, ethyl acetate was added and stirred, the organic layer was separated, and moisture was removed with magnesium sulfate. The solution was concentrated under reduced pressure, recrystallized with heptane, and then filtered to obtain <A-4>. (65 g, 72.4%)

Synthesis Example 1-5: Synthesis of A-5

<A-5a> <A-5>

Add 100 g of <A-5a> and 1000 mL of DMF to the reactor and slowly add 94.5 g of NBS dropwise. Add dropwise and stir for 2 hours. Afterwards, water is added dropwise and the solid is filtered. Dissolve it in dichloromethane and wash it with distilled water. After washing with water, dichloromethane was concentrated, heptane was added, crystals were captured and dried, and <A-5> was obtained. (132 g, 93.4%)

Synthesis Example 1-6: Synthesis of A-6

<A-5> <A-6a> <A-6>

Into the reactor, add 170 g of <A-5>, 97.3 g of <A-6a>, 14.8 g of tetrakis(triphenylphosphine)palladium(0), 176.5 g of potassium carbonate, 1000 mL of toluene, 500 mL of ethanol, and 500 mL of distilled water. It was stirred under reflux and then reacted for one day. After confirming the completion of the reaction by TLC, the temperature is lowered to room temperature, then distilled water and ethyl acetate are added, and then extracted. Ethyl acetate was concentrated, purified by column chromatography, and recrystallized to obtain <A-6>. (157.8 g, 92.0%)

Synthesis Example 1-7: Synthesis of A-7

<A-6> <A-7>

<A-7> was obtained by synthesis in the same manner, except that <A-6> was used instead of <A-5a> used in Synthesis Example 1-5. (yield 92.1%)

Synthesis Example 1-8: Synthesis of [BH-1]

<A-7> <A-4> [BH-1]

In a 500 mL round bottom flask, add 16 g of <A-7>, 25.24 g of <A-4>, 0.52 g of palladium(II) acetate, 1.53 g of (rac)-BIDIME, 13.32 g of sodium tertiary butoxide, and 160 mL of toluene. It was added, refluxed and stirred for 2 days. After confirming the completion of the reaction by thin layer chromatography, the reaction solution was cooled to room temperature, the reaction solution was extracted with water and dichloromethane, and the organic layer was concentrated under reduced pressure. The material was purified by column chromatography and recrystallized with tetrahydrofuran and acetone to obtain [BH-1]. (6.7g, 25.9%)

MS (MALDI-TOF): m/z 585.30 [M ⁺ ]

Synthesis Example 2. Synthesis of [BH-2]

Synthesis Example 2-1: Synthesis of BH-2

<A-4> [BH-2]

[BH-2] was obtained by synthesis in the same manner, except that 9-bromo-10-phenylanthracene was used instead of <A-7> used in Synthesis Example 1-8. (yield 71.2%)

MS (MALDI-TOF): m/z 572.21 [M ⁺ ]

Synthesis Example 3. Synthesis of [BH-3]

Synthesis Example 3-1: Synthesis of C-1

<C-1>

<C-1> was obtained by synthesis in the same manner, except that 3-aminodibenzofuran was used instead of 2-aminodibenzofuran used in Synthesis Example 1-1. (yield 71.2%)

Synthesis Example 3-2: Synthesis of C-2

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

<C-2> was obtained by synthesis in the same manner, except that <C-1> was used instead of <A-1> used in Synthesis Example 1-2. (yield 77.9%)

Synthesis Example 3-3: Synthesis of C-3

<C-2> <C-3>

<C-3> was obtained by synthesis in the same manner, except that <C-2> was used instead of <A-2> used in Synthesis Example 1-3. (yield 73.1%)

Synthesis Example 3-4: Synthesis of C-4

<C-3> <C-4>

<C-4> was obtained by synthesis in the same manner, except that <C-3> was used instead of <A-3> used in Synthesis Example 1-4. (yield 68.4%)

Synthesis example 3-5: [BH- 3] of synthesis

<A-7> <C-4> [BH-3]

[BH-3] was obtained by synthesis in the same manner, except that <C-4> was used instead of <A-4> used in Synthesis Example 1-8. (yield 73.2%)

MS (MALDI-TOF): m/z 630.28 [M ⁺ ]

Synthesis Example 4. Synthesis of [BH-4]

Synthesis example 4-1: [BH- 4] of synthesis

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

[BH-4] was synthesized in the same manner except that <D-1a> was used instead of <A-7> used in Synthesis Example 1-8, and <C-4> was used instead of <A-4>. got it (yield 74.8%)

MS (MALDI-TOF): m/z 622.23 [M ⁺ ]

Synthesis Example 5. Synthesis of [BH-5]

Synthesis Example 5-1: Synthesis of E-1

<E-1a> <E-1b> <E-1>

<E-1> was synthesized in the same manner except that <E-1a> was used instead of <A-5> used in Synthesis Example 1-6, and <E-1b> was used instead of <A-6a>. got it (yield 82.7%)

Synthesis Example 5-2: Synthesis of E-2

<E-1> <E-2>

<E-2> was obtained by synthesis in the same manner, except that <E-1> was used instead of <A-5a> used in Synthesis Example 1-5. (yield 89.3%)

Synthesis example 5-3: [BH- 5] of synthesis

<E-2> <C-4> [BH-5]

[BH-5] was synthesized in the same manner except that <E-2> was used instead of <A-7> used in Synthesis Example 1-8, and <C-4> was used instead of <A-4>. got it (yield 69.3%)

MS (MALDI-TOF): m/z 672.25 [M ⁺ ]

Synthesis Example 6. Synthesis of [BH-6]

Synthesis Example 6-1: Synthesis of F-1

<F-1>

<F-1> was obtained by synthesis in the same manner, except that 3-aminodibenzothiophene was used instead of 2-aminodibenzofuran used in Synthesis Example 1-1. (yield 75.1%)

Synthesis Example 6-2: Synthesis of F-2

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

<F-2> was obtained by synthesis in the same manner, except that <F-1> was used instead of <A-1> used in Synthesis Example 1-2. (yield 74.8%)

Synthesis Example 6-3: Synthesis of F-3

<F-2> <F-3>

<F-3> was obtained by synthesis in the same manner, except that <F-2> was used instead of <A-2> used in Synthesis Example 1-3. (yield 74.5%)

Synthesis Example 6-4: Synthesis of F-4

<F-3> <F-4>

<F-4> was obtained by synthesis in the same manner, except that <F-3> was used instead of <A-3> used in Synthesis Example 1-4. (yield 65.2%)

Synthesis example 6-5: [BH- 6] of synthesis

<F-5a> <F-4> [BH-6]

[BH-6] was synthesized in the same manner except that <F-5a> was used instead of <A-7> used in Synthesis Example 1-8, and <F-4> was used instead of <A-4>. got it (yield 59.3%)

MS (MALDI-TOF): m/z 664.22 [M ⁺ ]

Synthesis Example 7. Synthesis of [BH-7]

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

<G-1a> <F-4> [BH-7]

[BH-7] was synthesized in the same manner except that <G-1a> was used instead of <A-7> used in Synthesis Example 1-8, and <F-4> was used instead of <A-4>. got it (yield 63.3%)

MS (MALDI-TOF): m/z 664.22 [M ⁺ ]

Synthesis Example 8. Synthesis of [BH-8]

Synthesis example 8-1: Synthesis of H-1

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

<H-1> was synthesized in the same manner except that <H-1a> was used instead of <A-5> used in Synthesis Example 1-6, and <H-1b> was used instead of <A-6a>. got it (yield 78.2%)

Synthesis example 8-2: Synthesis of H-2

<H-1> <H-2>

<H-2> was obtained by synthesis in the same manner, except that <H-1> was used instead of <A-5a> used in Synthesis Example 1-5. (yield 84.1%)

Synthesis example 8-3: [BH- 8] of synthesis

<H-2> <A-4> [BH-8]

[BH-8] was obtained by synthesis in the same manner, except that <H-2> was used instead of <A-7> used in Synthesis Example 1-8. (yield 78.2%)

MS (MALDI-TOF): m/z 737.27 [M ⁺ ]

Synthesis Example 9: Synthesis of [BD-1]

Synthesis Example 9-1: Synthesis of I-1

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

In a round bottom flask, add 50 g of <I-1a>, 26.2 g of aniline, 4.3 g of tris(dibenzyrideneacetone)dipalladium, 1.9 g of tritertiary butylphosphine, 45.1 g of sodium tertiary butoxide, and 500 mL of toluene. and refluxed for 12 hours. After completion of the reaction, the reactants were separated into layers, and the organic layer was concentrated under reduced pressure and separated by column to obtain <I-1>. (45 g, 85%)

Synthesis Example 9-2: Synthesis of I-2

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

In a round bottom flask, 45 g of <I-1>, 49.6 g of <I-2a>, 3.7 g of tris(dibenzyrideneacetone)dipalladium, 1.6 g of tritertiary butylphosphine, 38.4 g of sodium tertiary butoxide, 450 mL of toluene was added and refluxed for 12 hours. After completion of the reaction, the reactants were separated into layers, and the organic layer was concentrated under reduced pressure and separated by column to obtain <I-2>. (59.2 g, 80%)

Synthesis Example 9-3: Synthesis of I-3

<I-2> <I-3a> <I-3>

In a round bottom flask, 30 g of <I-2>, 13.7 g of diphenylamine, 1.5 g of tris(dibenzyrideneacetone)dipalladium, 0.7 g of tritertiary butylphosphine, 15.6 g of sodium tertiary butoxide, and 300 toluene. mL was added and refluxed for 12 hours. After completion of the reaction, the reactants were separated into layers, and the organic layer was concentrated under reduced pressure and separated by column to obtain <I-3>. (31.8 g, 78%)

Synthesis Example 9-4: Synthesis of [BD-1]

<I-3> [BD-1]

31.8 g of <I-3> and 250 mL of tertiary butylbenzene were added to a round bottom flask and stirred under a nitrogen atmosphere. After lowering the temperature to -30°C, 93 mL of 1.7 M tertiary butyllithium was added dropwise and stirred at 60°C for 3 hours. After lowering the temperature to -20°C, 31.7 g of boron tribromide was added and stirred at room temperature for 1 hour. Afterwards, 16.3 g of diisopropylethylamine was added and stirred at 120°C for 3 hours. After completion of the reaction, the reactants were separated into layers, the organic layer was concentrated under reduced pressure, separated on a column, and recrystallized to obtain [BD-1]. (4.5 g, 15%)

MS (MALDI-TOF): m/z 476.15 [M ⁺ ]

Synthesis Example 10: Synthesis of [BD-2]

Synthesis Example 10-1: Synthesis of J-1

<J-1a> <J-1b> <J-1>

<J-1> was synthesized in the same manner except that <J-1a> was used instead of <I-1a> and <J-1b> was used instead of <I-1b> in Synthesis Example 9-1. got it (yield 73%)

Synthesis Example 10-2: Synthesis of J-2

<J-1> <J-2a> <J-2>

<J-2> was synthesized in the same manner except that <J-1> was used instead of <I-1> used in Synthesis Example 9-2, and <J-2a> was used instead of <I-2a>. got it (yield 71%)

Synthesis Example 10-3: Synthesis of J-3

<J-2> <J-3a> <J-3>

<J-3> was synthesized in the same manner except that <J-2> was used instead of <I-2> and <J-3a> was used instead of <I-3a> in Synthesis Example 9-3. got it (yield 78%)

Synthesis Example 10-4: Synthesis of [BD-2]

<J-3> [BD-2]

[BD-2] was obtained by synthesis in the same manner, except that <J-3> was used instead of <I-3> used in Synthesis Example 9-4. (yield 14%)

MS (MALDI-TOF): m/z 867.48 [M ⁺ ]

Synthesis Example 11: Synthesis of [BD-3]

Synthesis Example 11-1: Synthesis of K-1

<K-1> <K-1a> <K-1>

<K-1> was synthesized in the same manner except that <K-1> was used instead of <I-1> used in Synthesis Example 9-2, and <K-1a> was used instead of <I-2a>. got it (yield 68%)

Synthesis Example 11-2: Synthesis of K-2

<K-2a> <K-2b> <K-2>

<K-2> was synthesized in the same manner except that <K-2b> was used instead of <I-1> and <K-2a> was used instead of <I-2a> in Synthesis Example 9-2. got it (yield 82%)

Synthesis Example 11-3: Synthesis of K-3

<K-1> <K-2> <K-3>

<K-3> was synthesized in the same manner except that <K-1> was used instead of <I-2> used in Synthesis Example 9-3, and <K-2> was used instead of <I-3a>. got it (yield 77%)

Synthesis Example 11-4: Synthesis of [BD-3]

<K-3> [BD-3]

[BD-3] was obtained by synthesis in the same manner, except that <K-3> was used instead of <I-3> used in Synthesis Example 9-4. (yield 14%)

MS (MALDI-TOF): m/z 1033.52 [M ⁺ ]

Examples 1 to 16: Preparation of organic light-emitting devices

The ITO glass was patterned so that the light emitting area was 2 mm × 2 mm in size and then cleaned. After mounting the ITO glass in a vacuum chamber and setting the base pressure to ¹ This [Acceptor-1] : [Formula F] = 2 : 98 was formed into a film (100 Å). [Formula F] was formed as a hole transport layer (550 Å), and then [Formula G] was formed as an electron blocking layer (50 Å). The light-emitting layer is composed of a host compound represented by [Formula 1] or [Formula 2] according to the present invention and the following [BD-1] to [BD-3] plates represented by [Formula 3] and [Formula 4] according to the present invention. One of the compounds (2 wt%) was mixed to form a film (200 Å), and then [Formula H] was formed as a hole blocking layer (50 Å), and [Formula E-1] and [Formula E-1] were formed as an electron transport layer. An organic light emitting device was manufactured by forming a film of 250 Å for [Formula E-2] at a ratio of 1:1, 10 Å for [Formula E-2] as an electron injection layer, and 1000 Å for Al (1000 Å). The emission characteristics of the organic light emitting device were measured at 0.4 mA.

[Formula F] [Formula G] [Formula H]

[Formula E-1] [Formula E-2] [Acceptor-1]

[BD-1] [BD-2] [BD-3]

Comparative Examples 1 to 16

An organic light emitting device was manufactured in the same manner, except that [RH-1] to [RH-4] were used instead of the host compounds used in the above examples, and [RD-1] and [RD-2] were used instead of the dopant compounds. The emission characteristics of the organic light emitting device were measured at 0.4 mA. The structures of [RH-1] to [RH-4], [RD-1], and [RD-2] are as follows.

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

[RH-4] [RD-1] [RD-2]

For the organic light-emitting devices manufactured according to Examples 1 to 16 and Comparative Examples 1 to 16, external quantum efficiency and lifespan were measured, and the results are shown in Table 1 below.

division host dopant External quantum efficiency (EQE, %) life span
(T97, hr) Example 1 BH-1 BD-1 11.6 240 Example 2 BH-2 BD-1 11.7 330 Example 3 BH-3 BD-1 11.1 250 Example 4 BH-4 BD-1 12.0 235 Example 5 BH-5 BD-1 11.6 255 Example 6 BH-6 BD-1 11.3 280 Example 7 BH-7 BD-1 11.9 225 Example 8 BH-8 BD-1 11.8 220 Example 9 BH-2 BD-2 12.2 310 Example 10 BH-3 BD-2 11.6 245 Example 11 BH-5 BD-2 12.4 260 Example 12 BH-6 BD-2 11.9 280 Example 13 BH-2 BD-3 12.4 325 Example 14 BH-3 BD-3 11.8 270 Example 15 BH-5 BD-3 12.6 255 Example 16 BH-6 BD-3 12.1 275 Comparative Example 1 RH-1 BD-1 9.8 125 Comparative Example 2 RH-2 BD-1 9.9 180 Comparative Example 3 RH-3 BD-1 10.1 175 Comparative Example 4 RH-4 BD-1 10.3 175 Comparative Example 5 RH-1 BD-2 10.2 165 Comparative Example 6 RH-3 BD-2 10.1 185 Comparative Example 7 RH-1 BD-3 10.3 185 Comparative Example 8 RH-3 BD-3 10.5 195 Comparative Example 9 BH-3 RD-1 10.1 130 Comparative Example 10 BH-6 RD-1 9.1 135 Comparative Example 11 RH-1 RD-1 9.2 105 Comparative Example 12 RH-3 RD-1 9.6 80 Comparative Example 13 BH-3 RD-2 10.1 135 Comparative Example 14 BH-6 RD-2 9.9 145 Comparative Example 15 RH-1 RD-2 9.3 100 Comparative Example 16 RH-3 RD-2 9.1 115

As can be seen in [Table 1], an organic light-emitting device employs an anthracene compound with a characteristic structure according to the present invention as a host material for the light-emitting layer, and a polycyclic ring compound with a characteristic structure according to the present invention as a dopant material for the light-emitting layer. It can be seen that the external quantum efficiency is superior to the organic light-emitting device (Comparative Examples 1 to 16) employing a compound that contrasts with the characteristic structure of the compound according to the present invention, and in particular, the lifespan characteristics are significantly improved.

Example 17 to 54: First light emitting layer and The second light emitting layer Manufacturing of organic light-emitting devices containing

The ITO glass was patterned so that the light emitting area was 2 mm × 2 mm in size and then cleaned. After mounting the ITO glass in a ^vacuum chamber, the base pressure was set to 1 Formed as, one of the first and second emitting layers is a host compound represented by [Formula 1] or [Formula 2] according to the present invention and [Formula 3] and [Formula 4] according to the present invention. A film (50 Å) was formed by mixing one of the following [BD-1] to [BD-3] dopant compounds (1 wt%), and the remaining layer was a film (50 Å) represented by [Formula 5] according to the present invention. One of the host compounds [BH-A] and [BH-B] and one of the following [BD-1] to [BD-3] dopant compounds represented by [Formula 2] and [Formula 3] according to the present invention ( 1 wt%) was mixed to form a film (150 Å), then as an electron transport layer, [E-1] and [E-2] were mixed at a ratio of (1:1) (300 Å), and as an electron injection layer, [E -2] (10 Å) and Al (1,000 Å) were deposited in the following order to manufacture an organic light emitting device. The light emission characteristics of the organic light emitting device were measured at 0.4 mA.

[DNTPD] [α-NPD] [E-1]

[E-2] [BH-A] [BH-B]

[BD-1] [BD-2] [BD-3]

Comparative example 17 to 39

Organic light-emitting devices were manufactured in the same manner except that [RH-1] to [RH-5], [RD-1], and [RD-2] were used instead of the compounds used in the above examples, and the organic light-emitting devices emit light. Characteristics were measured at 0.4 mA. The structure of [RH-5] is as follows.

[RH-5]

For the organic light-emitting devices manufactured according to Examples 17 to 54 and Comparative Examples 17 to 39, external quantum efficiency and lifespan were measured, and the results are shown in Table 2 below.

First light emitting layer Second light emitting layer External quantum efficiency (EQE, %) life span
(T97, hr) host dopant host dopant Example 17 BH-2 BD-1 BH-A BD-1 13.1 385 Example 18 BH-2 BD-2 BH-A BD-2 13.4 365 Example 19 BH-2 BD-3 BH-A BD-3 13.8 360 Example 20 BH-2 BD-1 BH-B BD-1 12.9 375 Example 21 BH-2 BD-2 BH-B BD-2 13.0 355 Example 22 BH-2 BD-3 BH-B BD-3 13.2 385 Example 23 BH-3 BD-1 BH-A BD-1 12.9 345 Example 24 BH-3 BD-2 BH-A BD-2 13.0 330 Example 25 BH-3 BD-3 BH-A BD-3 13.2 345 Example 26 BH-3 BD-1 BH-B BD-1 12.6 350 Example 27 BH-3 BD-2 BH-B BD-2 12.7 345 Example 28 BH-3 BD-3 BH-B BD-3 12.9 360 Example 29 BH-4 BD-1 BH-A BD-1 13.1 355 Example 30 BH-4 BD-2 BH-A BD-2 13.3 360 Example 31 BH-4 BD-3 BH-A BD-3 13.5 370 Example 32 BH-4 BD-1 BH-B BD-1 12.8 355 Example 33 BH-4 BD-2 BH-B BD-2 12.9 350 Example 34 BH-4 BD-3 BH-B BD-3 13.1 365 Example 35 BH-5 BD-1 BH-A BD-1 13.7 315 Example 36 BH-5 BD-2 BH-A BD-2 13.9 305 Example 37 BH-5 BD-3 BH-A BD-3 14.1 290 Example 38 BH-5 BD-1 BH-B BD-1 13.2 325 Example 39 BH-5 BD-2 BH-B BD-2 13.3 325 Example 40 BH-5 BD-3 BH-B BD-3 13.5 315 Example 41 BH-6 BD-1 BH-A BD-1 13.4 305 Example 42 BH-6 BD-2 BH-A BD-2 13.5 305 Example 43 BH-6 BD-3 BH-A BD-3 13.6 315 Example 44 BH-6 BD-1 BH-B BD-1 13.1 320 Example 45 BH-6 BD-2 BH-B BD-2 13.2 330 Example 46 BH-6 BD-3 BH-B BD-3 13.4 330 Example 47 BH-2 BD-2 BH-A BD-3 14.2 355 Example 48 BH-2 BD-1 BH-A BD-3 14.0 345 Example 49 BH-3 BD-2 BH-A BD-3 13.7 340 Example 50 BH-3 BD-1 BH-A BD-3 13.9 350 Example 51 BH-A BD-1 BH-5 BD-1 13.9 330 Example 52 BH-A BD-2 BH-5 BD-2 14.0 315 Example 53 BH-B BD-2 BH-5 BD-2 13.5 340 Example 54 BH-B BD-3 BH-5 BD-3 13.6 355 Comparative Example 17 RH-1 BD-1 BH-A BD-1 10.7 200 Comparative Example 18 RH-1 BD-2 BH-A BD-2 10.9 195 Comparative Example 19 RH-1 BD-3 BH-A BD-3 11.1 200 Comparative Example 20 RH-1 BD-1 BH-B BD-1 10.9 205 Comparative Example 21 RH-1 BD-2 BH-B BD-2 11.0 195 Comparative Example 22 RH-1 BD-3 BH-B BD-3 11.2 215 Comparative Example 23 RH-2 BD-1 BH-A BD-1 11.2 185 Comparative Example 24 RH-2 BD-2 BH-A BD-2 11.4 165 Comparative Example 25 RH-2 BD-3 BH-A BD-3 11.5 170 Comparative Example 26 RH-2 BD-1 BH-B BD-1 10.9 165 Comparative Example 27 RH-2 BD-2 BH-B BD-2 11.0 160 Comparative Example 28 RH-2 BD-3 BH-B BD-3 11.2 175 Comparative Example 29 RH-1 RD-1 BH-A RD-1 8.6 135 Comparative Example 30 RH-1 RD-2 BH-A RD-2 8.8 120 Comparative Example 31 RH-2 RD-1 BH-A RD-1 8.4 130 Comparative Example 32 RH-2 RD-2 BH-A RD-2 8.5 115 Comparative Example 33 BH-1 RD-1 BH-A RD-1 9.4 190 Comparative Example 34 BH-1 RD-2 BH-A RD-2 9.6 185 Comparative Example 35 BH-6 RD-2 BH-A RD-2 9.5 150 Comparative Example 36 BH-6 RD-3 BH-A RD-3 9.3 145 Comparative Example 37 BH-1 RD-1 BH-B RD-1 9.7 215 Comparative Example 38 BH-1 RD-2 BH-B RD-1 9.7 205 Comparative Example 39 RH-1 RD-2 BH-5 RD-2 8.2 145

As can be seen in [Table 2], an anthracene compound with a characteristic structure according to the present invention is used as a host material for the light-emitting layer, and a polycyclic ring compound with a characteristic structure according to the present invention is used as a light-emitting layer dopant material to form a plurality of light-emitting layers. It can be seen that the constructed organic light-emitting device has superior external quantum efficiency compared to the organic light-emitting device (Comparative Examples 17 to 39) employing a compound that contrasts with the characteristic structure of the compound according to the present invention, and in particular, the lifespan characteristics are significantly improved. You can.

Claims (15)

first electrode; And a second electrode facing the first electrode,
a first light emitting layer including a first host and a first dopant between the first electrode and the second electrode; and a second light-emitting layer including a first host and a second dopant,
An organic light-emitting device, wherein at least one of the first host and the second host includes one or more anthracene compounds represented by the following [Formula 1] or [Formula 2]:
[Formula 1] [Formula 2]

In [Formula 1] to [Formula 2],
R is hydrogen or deuterium,
R ₁ to R ₉ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group with 2 to 30 carbon atoms, and a substituted or unsubstituted carbon number. Alkenyl group of 2 to 30 carbon atoms, substituted or unsubstituted aryl group of 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted Ringed heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms Aryloxy 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 Any one selected from an unsubstituted germanium group, nitro group, cyano group, and halogen group,
Ar ₁ to Ar ₃ are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms. Any one selected from 30 aliphatic aromatic mixed ring groups,
X is O or S,
L is a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms,
n is an integer of 1 to 3, and when n is an integer of 2 or more, the plurality of Ls are the same or different from each other,
m is an integer of 4, and each of the plurality of R ₉ is the same as or different from each other,
The plurality of R ₉ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring is selected from N, S and O. may be substituted with one or more heteroatoms,
'Substitution' in 'substituted or unsubstituted' in [Formula 1] and [Formula 2] means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, halogenation with 1 to 24 carbon atoms. alkyl group, cycloalkyl group with 3 to 30 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, arylalkyl group with 7 to 24 carbon atoms , alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 2 to 24 carbon atoms, aliphatic aromatic mixed ring group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, and 1 to 2 carbon atoms. Substituted with one or more substituents selected from the group consisting of an amine group of 24, a silyl group of 1 to 24 carbon atoms, a germanium group of 1 to 24 carbon atoms, an aryloxy group of 6 to 24 carbon atoms, and an arylthionyl group of 6 to 24 carbon atoms. This means that, in two or more cases, they are the same or different from each other, and one or more hydrogens in each substituent can be replaced with deuterium. According to paragraph 1,
[Formula 1] is an organic light emitting device represented by any one selected from the following [Formula 1-1] to [Formula 1-5]:
[Formula 1-1] [Formula 1-2]

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

[Formula 1-5]

In [Formula 1-1] to [Formula 1-5],
X ₁ is any one selected from O, S and CR ₁₁ R ₁₂ ,
R ₁₀ is each independently hydrogen, deuterium, a deuterium-substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a deuterium-substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, and a deuterium-substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms Any one selected from aliphatic aromatic mixed ring groups,
R ₁₁ and R ₁₂ are the same or different from each other, and are each independently a deuterium-substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
p is an integer of 5, q is an integer of 7, r is an integer of 9, s is an integer of 9, t is an integer of 7, and the plurality of R ₁₀ are the same or different from each other,
The plurality of R ₁₀ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
R ₁₁ and R ₁₂ may each be linked to form an alicyclic or aromatic monocyclic or polycyclic ring,
The carbon atom of the formed alicyclic, aromatic mono- or polycyclic ring may be substituted with any one or more heteroatoms selected from N, S and O,
X, n, m, L, Ar ₁ , Ar ₂ , R and R ₁ to R ₉ are the same as defined in [Formula 1] in paragraph 1 above. According to paragraph 1,
[Formula 2] is an organic light emitting device represented by any one selected from the following [Formula 2-1] to [Formula 2-5]:
[Formula 2-1] [Formula 2-2]

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

[Formula 2-5]

In [Formula 2-1] to [Formula 2-5],
X ₁ is any one selected from O, S and CR ₁₁ R ₁₂ ,
R ₁₀ is each independently hydrogen, deuterium, a deuterium-substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a deuterium-substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, and a deuterium-substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms Any one selected from aliphatic aromatic mixed ring groups,
R ₁₁ and R ₁₂ are the same or different from each other, and are each independently a deuterium-substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
p is an integer of 5, q is an integer of 7, r is an integer of 9, s is an integer of 9, t is an integer of 7, and the plurality of R ₁₀ are the same or different from each other,
The plurality of R ₁₀ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
R ₁₁ and R ₁₂ may each be linked to form an alicyclic or aromatic monocyclic or polycyclic ring,
The carbon atom of the formed alicyclic, aromatic mono- or polycyclic ring may be substituted with any one or more heteroatoms selected from N, S and O,
X, n, m, L, Ar ₁ , Ar ₂ , R and R ₁ to R ₉ are the same as defined in [Formula 2] in paragraph 1 above. According to paragraph 1,
In the [Formula 1] and [Formula 2], L is an organic light emitting device selected from the following [Structural Formula 1] to [Structural Formula 5]:
[Structural Formula 1] [Structural Formula 2] [Structural Formula 3]

[Structural Formula 4] [Structural Formula 5]
According to paragraph 1,
[Formula 1] or [Formula 2] is an organic light emitting device characterized in that any one selected from the following compounds:





According to paragraph 1,
One of the first host and the second host includes one or more anthracene compounds represented by [Formula 1] or [Formula 2], and the remaining one of the first host and the second host has the following [Formula 5]: Organic light-emitting device characterized in that it contains one or more anthracene compounds as indicated:
[Formula 5]

In [Formula 5] above,
X ₂ is O or S,
Ar ₄ is any one selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, 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. and
R ₅₁ to R ₆₆ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group with 2 to 30 carbon atoms, or a substituted or unsubstituted carbon number. Alkenyl group of 2 to 30 carbon atoms, substituted or unsubstituted aryl group of 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted Ringed heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms Aryloxy 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 It is any one selected from unsubstituted germanium group, nitro group, cyano group and halogen group,
L ₁ is a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms,
o is an integer of 1 to 3, and when o is 2 or more, the plurality of L ₁ are the same or different from each other,
Each of the adjacent R ₅₉ to R ₆₆ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring are N, S and may be substituted with any one or more heteroatoms selected from O,
In the above [Formula 5], 'substituted' in 'substituted or unsubstituted' means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, halogenated alkyl group with 1 to 24 carbon atoms, and 3 carbon atoms. Cycloalkyl group of 30 to 30 carbon atoms, alkenyl group of 2 to 24 carbon atoms, alkynyl group of 2 to 24 carbon atoms, heteroalkyl group of 1 to 24 carbon atoms, aryl group of 6 to 24 carbon atoms, arylalkyl group of 7 to 24 carbon atoms, 7 to 24 carbon atoms alkylaryl group, heteroaryl group with 2 to 24 carbon atoms, heteroarylalkyl group with 2 to 24 carbon atoms, aliphatic aromatic mixed ring group with 3 to 24 carbon atoms, alkoxy group with 1 to 24 carbon atoms, amine group with 1 to 24 carbon atoms, It means being substituted with one or more substituents selected from the group consisting of a silyl group with 1 to 24 carbon atoms, a germanium group with 1 to 24 carbon atoms, an aryloxy group with 6 to 24 carbon atoms, and an arylthionyl group with 6 to 24 carbon atoms, and two or more In these cases, they are the same or different from each other, and one or more hydrogens in each substituent can be replaced with deuterium. According to clause 6,
At least four of R ₁ to R ₈ in [Formula 1] or [Formula 2] are deuterium, and at least four of R ₅₁ to R ₅₈ in [Formula 5] are deuterium. first electrode; And a second electrode facing the first electrode,
It includes an organic layer interposed between the first electrode and the second electrode,
The organic layer includes a light-emitting layer, and the light-emitting layer includes a host and a dopant,
The host includes at least one anthracene compound represented by the following [Formula 1] or [Formula 2], and the dopant includes at least one polycyclic ring compound represented by the following [Formula 3] or [Formula 4] Organic light emitting device containing:
[Formula 1] [Formula 2]

In [Formula 1] to [Formula 2],
R is hydrogen or deuterium,
R ₁ to R ₉ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group with 2 to 30 carbon atoms, and a substituted or unsubstituted carbon number. Alkenyl group of 2 to 30 carbon atoms, substituted or unsubstituted aryl group of 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted Ringed heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms Aryloxy 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 Any one selected from an unsubstituted germanium group, nitro group, cyano group, and halogen group,
Ar ₁ to Ar ₃ are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms. Any one selected from 30 aliphatic aromatic mixed ring groups,
X is O or S,
L is a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms,
n is an integer of 1 to 3, and when n is an integer of 2 or more, the plurality of Ls are the same or different from each other,
m is an integer of 4, and each of the plurality of R ₉ is the same as or different from each other,
The plurality of R ₉ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,

[Formula 3] [Formula 4]

In [Formula 3] and [Formula 4],
Y ₃ is O or S,
Y ₁ and Y ₂ are the same as or different from each other, and are each independently NR ₁₄ , O, S, CR ₁₅ R ₁₆ , SiR ₁₇ R ₁₈ or GeR ₁₉ R ₂₀ ,
A ₁ to A ₃ are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 3 to 50 carbon atoms. Any one selected from an aliphatic ring having 30 to 30 carbon atoms and a substituted or unsubstituted aliphatic aromatic mixed ring having 3 to 30 carbon atoms,
R ₁₄ to R ₂₀ are the same or different from each other, and each independently represents hydrogen, deuterium, 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 alkynyl group. Alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group with 3 to 30 carbon atoms, substituted or Unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted carbon number 6 to 30 Aryloxy 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 any one selected from unsubstituted germanium group, nitro group, cyano group and halogen group,
R ₁₄ to R ₂₀ may be connected to the A ₁ to A ₃ rings to further form an alicyclic or aromatic monocyclic or polycyclic ring,
R ₁₅ and R ₁₆ , R ₁₇ and R ₁₈ , and R ₁₉ and R ₂₀ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
The carbon atoms of the alicyclic, aromatic, monocyclic or polycyclic ring may be substituted with one or more heteroatoms selected from N, S and O,
'Substitution' in 'substituted or unsubstituted' in [Formula 1] to [Formula 4] means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, halogenation with 1 to 24 carbon atoms. alkyl group, cycloalkyl group with 3 to 30 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, arylalkyl group with 7 to 24 carbon atoms , alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 2 to 24 carbon atoms, aliphatic aromatic mixed ring group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, and 1 to 2 carbon atoms. Substituted with one or more substituents selected from the group consisting of an amine group of 24, a silyl group of 1 to 24 carbon atoms, a germanium group of 1 to 24 carbon atoms, an aryloxy group of 6 to 24 carbon atoms, and an arylthionyl group of 6 to 24 carbon atoms. This means that, in two or more cases, they are the same or different from each other, and one or more hydrogens in each substituent can be replaced with deuterium. According to clause 8,
The [Formula 3] is represented by the following [Formula 3-1] to [Formula 3-3], and [Formula 4] is an organic light emitting device represented by the following [Formula 4-1] to [Formula 4-3]:
[Formula 3-1] [Formula 4-1]

In [Formula 3-1] and [Formula 4-1],
The definitions of Y ₁ to Y ₃ are the same as those defined in [Formula 3] and [Formula 4] in Article 8 above,
Z ₁ to Z ₁₀ are the same as or different from each other, and are each independently CR ₃₁ or N,
When two or more of Z ₁ to Z ₁₀ are each CR ₃₁ , each R ₃₁ is the same or different from each other,
When the two or more adjacent Z ₁ to Z ₁₀ are each CR ₃₁ , each R ₃₁ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
R ₂₁ to R ₃₁ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group with 2 to 30 carbon atoms, or a substituted or unsubstituted carbon number. Alkenyl group of 2 to 30 carbon atoms, substituted or unsubstituted aryl group of 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted Ringed heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms Aryloxy 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 It is any one selected from unsubstituted germanium group, nitro group, cyano group and halogen group,
Substituents adjacent to each other among R ₂₁ to R ₃₀ may be connected to each other to further form an alicyclic or aromatic mono- or polycyclic ring,
When Z ₈ and Z ₉ are CR 31, R ₂₁ , R ₂₅ , R ₂₆ and R ₃₀ may be combined with each R ₃₁ to form _an additional alicyclic or aromatic monocyclic or polycyclic ring,
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 ₃₂ to R ₃₆ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group with 2 to 30 carbon atoms, and a substituted or unsubstituted carbon number. Alkenyl group of 2 to 30 carbon atoms, substituted or unsubstituted aryl group of 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group of 3 to 30 carbon atoms, substituted or unsubstituted Ringed heterocycloalkyl group having 1 to 30 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 carbon number 1 to 30 alkoxy group, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, substituted or unsubstituted Any one selected from an amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group,
The adjacent substituents of R ₃₂ to R ₃₆ may be connected to form an additional alicyclic or aromatic monocyclic or polycyclic ring,

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

In [Formula 3-2] and [Formula 4-2],
The definitions of Y ₁ to Y ₃ are the same as those defined in [Formula 3] and [Formula 4] in Article 8 above,
Z ₁ to Z ₁₀ are the same as or different from each other, and are each independently CR ₃₁ or N,
When two or more of Z ₁ to Z ₁₀ are each CR ₃₁ , each R ₃₁ is the same or different from each other,
When two or more adjacent Z ₁ to Z ₈ are each CR ₃₁ , each R ₃₁ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
M is Si or Ge,
R ₃₁ and R ₃₇ to R ₃₉ are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, substituted or unsubstituted A substituted or unsubstituted 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 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, Substituted or unsubstituted heterocycloalkyl group having 1 to 30 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 carbon atoms Alkoxy group of 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group of 6 to 30 carbon atoms, substituted or unsubstituted alkylthoxy group of 1 to 30 carbon atoms, substituted or unsubstituted arylthoxy group of 5 to 30 carbon atoms, substituted or any one selected from an unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group,
R ₃₇ to R ₃₉ 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 are each independently CR ₃₁ or N,
When two or more of Z ₁ to Z ₁₁ are each CR ₃₁ , each R ₃₁ is the same or different from each other,
When the two or more adjacent Z ₁ to Z ₁₁ are each CR ₃₁ , each R ₃₁ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
The definitions of Y ₁ to Y ₃ are the same as those defined in [Formula 3] and [Formula 4] in Article 8 above,
However, at least one of Y ₁ and Y ₂ is a linking group shown in [Structural Formula B] below,
[Structural Formula B]

In [Structural Formula B], [Formula 3-3], and [Formula 4-3],
X ₂ is O or S,
R ₃₁ and R ₄₁ to R ₄₈ are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, substituted or unsubstituted A substituted or unsubstituted 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 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 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 carbon number 6 Aryloxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, substituted or unsubstituted amine group, substituted or unsubstituted silyl group , a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group,
Any one of R ₄₁ to R ₄₈ is bonded to Y ₁ or Y ₂ by a single bond with a nitrogen atom, and R ₄₁ to R ₄₈ excluding this is bonded to each other or adjacent substituents to form an alicyclic or aromatic single ring. Or it can form a polycyclic ring,
The carbon atoms of the additionally formed alicyclic, aromatic mono- or polycyclic rings in [Formula 3-1] to [Formula 4-3] may be substituted with any one or more heteroatoms selected from N, S and O,
'Substitution' in 'substituted or unsubstituted' in [Formula 3-1] to [Formula 4-3] means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, and 1 carbon atom. Halogenated alkyl group of 2 to 24 carbon atoms, cycloalkyl group of 3 to 30 carbon atoms, alkenyl group of 2 to 24 carbon atoms, alkynyl group of 2 to 24 carbon atoms, heteroalkyl group of 1 to 24 carbon atoms, aryl group of 6 to 30 carbon atoms, and 7 to 7 carbon atoms. Arylalkyl group of 30, alkylaryl group of 7 to 30 carbon atoms, heteroaryl group of 2 to 30 carbon atoms, heteroarylalkyl group of 2 to 24 carbon atoms, aliphatic aromatic mixed ring group of 3 to 30 carbon atoms, alkoxy group of 1 to 24 carbon atoms , 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, an aryloxy group having 6 to 24 carbon atoms, and an arylthionyl group having 6 to 24 carbon atoms. It means being substituted with, and in the case of two or more, they are the same or different from each other, and one or more hydrogens in each substituent can be replaced with deuterium. According to clause 8,
[Formula 3] to [Formula 4] are organic light emitting devices selected from compounds represented by the following formulas:



According to clause 8,
The dopant in the light-emitting layer is an organic light-emitting device used by mixing or stacking one or more compounds in addition to one compound represented by [Formula 3] to [Formula 4]. According to clause 8,
The host of the light-emitting layer is an organic light-emitting device used by mixing or stacking one or more compounds in addition to one compound represented by [Formula 1] or [Formula 2]. According to paragraph 1,
An organic light-emitting device used by mixing or stacking one or more compounds in addition to one anthracene compound represented by [Formula 1] or [Formula 2]. According to clause 6,
An organic light-emitting device used by mixing or stacking one or more compounds in addition to one anthracene compound represented by [Formula 5]. According to claim 1 or 8,
The organic light emitting device may include a flat panel display device; flexible display device; Devices for monochromatic or white flat panel lighting; Devices for flexible lighting, either monochromatic or white; Vehicle display devices; and a display device for virtual or augmented reality. An organic light emitting device used in any one device selected from the group consisting of: