KR20230038150A - Organic light-emitting compound and organic light-emitting device comprising the same - Google Patents

Abstract

The present invention relates to an anthracene derivative compound with a characteristic structure and an organic light emitting device including the same. More specifically, the present invention relates to an organic light emitting device with significantly improved long lifespan and low voltage characteristics by adopting an anthracene derivative compound having a characteristic structure as a host compound and a polycyclic aromatic derivative compound having a characteristic structure as a dopant compound in a light emitting layer.

Description

Organic light-emitting compound and organic light-emitting device comprising the same {Organic light-emitting compound and organic light-emitting device comprising the same}

The present invention relates to an organic light emitting compound and an organic light emitting device including the same, and more specifically, an anthracene derivative having a characteristic structure is used as a host compound and a polycyclic aromatic derivative compound is used as a dopant compound in a light emitting layer to provide long lifespan and low voltage characteristics. This remarkably improved organic light emitting device is related.

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

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

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

Accordingly, an object of the present invention is to provide an organic light emitting device having remarkably improved low-voltage driving and long lifespan characteristics by employing characteristic host materials and dopant materials for the light emitting layer in the organic light emitting device.

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

[Formula A]

The characteristic structure of [Formula A], specific compounds implemented thereby, and Ar ₁ , R ₁ to R ₁₄ , L ₁ and X will be described later.

In addition, in order to solve the above problems, the present invention includes a first electrode, a second electrode opposite to the first electrode, and a light emitting layer interposed between the first electrode and the second electrode, and the [Formula A] It provides an organic light emitting device including the compound to be displayed in the light emitting layer.

The organic light emitting device according to the present invention employs a dopant compound represented by the following [Formula D-1] or [Formula D-2] together with the compound represented by [Formula A] in the light emitting layer to further include characterized by

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

The characteristic structures of [Formula D-1] and [Formula D-2], specific compounds implemented thereby, and X ₁ , Y ₁ to Y ₃ and A ₁ to A ₃ will be described later.

The organic light emitting device according to the present invention employs an anthracene derivative compound having a characteristic structure as a host and a polycyclic aromatic derivative compound as a dopant in the light emitting layer to realize a long lifespan and low voltage organic light emitting device with remarkably improved lifetime characteristics. It can be usefully used for various display devices such as flat screen, flexible, and wearable displays as well as devices.

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

One aspect of the present invention relates to a compound represented by the following [Chemical Formula A], characterized in that it structurally includes at least one benzofuran or benzothiophene in the structure, through which a host compound in the light emitting layer of an organic light emitting device It is possible to implement an organic light emitting device having long lifespan and low voltage characteristics.

[Formula A]

In the above [Formula A],

Ar ₁ 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 ₁ to R ₁₄ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted carbon atom. An alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, substituted or unsubstituted Ringed heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms Group, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 6 to 50 carbon atoms, substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, substituted or unsubstituted carbon atoms Arylamine group having 6 to 50 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring having 3 to 50 carbon atoms groups, cyano groups, nitro groups and halogen groups.

Any one of R ₉ and R ₁₀ binds to the linking group L ₁ .

X is an oxygen atom (O) or a sulfur atom (S).

L ₁ is a divalent linking group, and is a single bond, or a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms. It is selected from aliphatic aromatic mixed ring groups.

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

'Substitution' in 'substituted or unsubstituted' means that each of Ar ₁ , R ₁ to R ₁₄ and L ₁ is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, or a carbon number 1 to 24 halogenated alkyl groups, cycloalkyl groups of 3 to 30 carbon atoms, alkenyl groups of 2 to 24 carbon atoms, alkynyl groups of 2 to 24 carbon atoms, heteroalkyl groups of 1 to 24 carbon atoms, aryl groups of 6 to 30 carbon atoms, 7 to 24 carbon atoms Arylalkyl group having 30 carbon atoms, alkylaryl group having 7 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 2 to 30 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, and 6 carbon atoms to 30 arylamino group, C2 to 30 heteroarylamino group, C1 to 24 alkylsilyl group, C6 to 30 arylsilyl group, C6 to 30 aryloxy group and C3 to 30 aliphatic aromatic mixture It means that it is substituted with one or more substituents selected from ring groups.

[Formula A] includes at least one deuterium atom (D), that is, in [Formula A], at least one of Ar ₁ , R ₁ to R ₁₄ and L ₁ or substituents thereof is deuterium. characterized by

According to one embodiment of the present invention, the deuteration degree of the anthracene derivative represented by [Formula A] is 10% or more, and 10% or more of the substituents introduced into the skeleton represented by [Formula A] are deuterium means to be

In addition, according to one embodiment of the present invention, the degree of deuteration of the anthracene derivative represented by [Formula A] is 30% or more.

In addition, the deuteration degree of the anthracene derivative represented by [Formula A] is characterized in that 50% or more.

According to one embodiment of the present invention, at least one of R ₁₁ to R ₁₄ is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted group. It may be any one selected from heteroaryl groups having 3 to 20 carbon atoms.

In addition, according to an embodiment of the present invention, at least one of R ₁₁ to R ₁₄ in [Formula A] is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, substituted or It may be an unsubstituted cycloalkyl group having 3 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

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

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

In [Formula A-1] and [Formula A-2],

Ar ₁₁ 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 ₂₁ to R ₃₃ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted carbon number. An alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, substituted or unsubstituted Ringed heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms Group, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 6 to 50 carbon atoms, substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, substituted or unsubstituted carbon atoms Arylamine group having 6 to 50 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring having 3 to 50 carbon atoms groups, cyano groups, nitro groups and halogen groups.

X is an oxygen atom (O) or a sulfur atom (S).

L ₂ is a divalent linking group, and is a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms. It is selected from aliphatic aromatic mixed ring groups.

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

'Substitution' in 'substituted or unsubstituted' means that each of Ar ₁₁ , R ₂₁ to R ₃₃ and L ₂ is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, or a carbon number 1 to 24 halogenated alkyl groups, cycloalkyl groups of 3 to 30 carbon atoms, alkenyl groups of 2 to 24 carbon atoms, alkynyl groups of 2 to 24 carbon atoms, heteroalkyl groups of 1 to 24 carbon atoms, aryl groups of 6 to 30 carbon atoms, 7 to 24 carbon atoms Arylalkyl group having 30 carbon atoms, alkylaryl group having 7 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 2 to 30 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, and 6 carbon atoms to 30 arylamino group, C2 to 30 heteroarylamino group, C1 to 24 alkylsilyl group, C6 to 30 arylsilyl group, C6 to 30 aryloxy group and C3 to 30 aliphatic aromatic mixture It means that it is substituted with one or more substituents selected from ring groups.

[Formula A-1] and [Formula A-2] each contain at least one deuterium atom (D), that is, in each of [Formula A-1] and [Formula A-2], the Ar ₁₁ , R ₂₁ to R ₃₃ and L ₂ or at least one of these substituents is characterized in that deuterium.

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

In addition, in the present invention, the meaning of 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 substituents' refer to the corresponding It may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located sterically 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 may be interpreted as 'adjacent substituents'.

In the present invention, the alkyl group may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. 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 and the like, but is not limited thereto.

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

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

In the present invention, the cycloalkyl group includes a monocyclic or polycyclic group and may be further substituted by another substituent, and the polycyclic group refers to a group in which a cycloalkyl group is directly connected or condensed with another cyclic group, and the other cyclic group is a cycloalkyl group. However, other types of ring groups such as heterocycloalkyl groups, aryl groups, and heteroaryl groups may also be used. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2 ,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but are not limited thereto.

In the present invention, the heterocycloalkyl group includes a heteroatom such as O, S, Se, N or Si, and also includes a monocyclic or polycyclic group, and may be further substituted by other substituents, and polycyclic refers to a heterocycloalkyl group. It refers to a group in which an alkyl group is directly connected or condensed with another ring group, and the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, and the like.

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

In the present invention, the heteroaryl group is a heterocyclic group containing a heteroatom, and examples thereof include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, Bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyr Also pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzo Furanyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, etc., but are not limited thereto. .

In the present invention, the aliphatic aromatic mixed ring means a ring in which two or more rings are connected and condensed, and the aliphatic ring and the aromatic ring are condensed to have non-aromaticity as a whole, and also a polycyclic aliphatic aromatic ring. In addition to C, heteroatoms selected from N, O, P and S may be included in the mixed ring.

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

In the present invention, the silyl group refers to an alkyl-substituted silyl group or an aryl-substituted silyl group, and specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, and dimethoxyphenylsilyl. , diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl and the like.

In the present invention, the amine group may be -NH ₂ , an alkylamine group, an arylamine group, etc., the arylamine group means an amine substituted with an aryl, the alkylamine group means an amine substituted with an alkyl, and the arylamine group Examples of are a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group, and the aryl group in the arylamine group may be a monocyclic aryl group. It may be a cyclic aryl group, and the arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. In addition, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present invention, the aryl group in the aryloxy group and arylthioxy group is the same as the above-mentioned aryl group, and specifically, the aryloxy group includes a phenoxy group, p-toryloxy group, m-toryloxy group, 3,5- Dimethyl-phenoxy group, 2,4,6-trimethylphenoxy 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-phenane There is a triloxy group, 9-phenanthryloxy group, and the like, and the arylthioxy group includes, but is not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group, and the like.

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

According to one embodiment of the present invention, the [Formula A] may be any one selected from compounds represented by the following [1] to [104], but the range is not limited thereby.

An organic light emitting device according to the present invention relates to an organic light emitting device composed of a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, and the organic layer, preferably, the light emitting layer. It is characterized in that it comprises an anthracene derivative compound represented by the [Formula A].

In addition, the light emitting layer is composed of a host and a dopant, the atracene derivative compound represented by [Formula A] is used as a host, and the light emitting layer contains one host compound other than one host compound represented by [Formula A]. It is characterized in that more than species are mixed or layered.

In addition, the organic light emitting device according to an embodiment of the present invention may further include a dopant compound in the light emitting layer in the device.

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

In this case, the organic layer in the organic light emitting device of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer.

As a more preferred embodiment of the present invention, in the present invention, the organic layer interposed between the first electrode and the second electrode includes a light emitting layer, the light emitting layer is made of a host and a dopant, and the [Formula A] may include at least one of the anthracene derivative compounds represented as a host material in the light emitting layer.

In addition, the dopant compound used in the light emitting layer in the present invention is represented by the following [Formula D-1] or [Formula D-2].

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

In [Formula D-1] and [Formula D-2],

X ₁ is any one selected from B, P=O and P=S.

Y ₁ to Y ₃ are each independently NR ₄₁ , CR ₄₂ R ₄₃ , O, S, Se and SiR ₄₄ R ₄₅ are selected from

A ₁ to A ₃ are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms, and It is selected from substituted or unsubstituted aliphatic aromatic mixed rings having 3 to 30 carbon atoms.

Wherein R ₄₁ to R ₄₅ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted carbon atom group. Cycloalkyl group having 3 to 30 carbon atoms, 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 alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted An unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylthio group having 1 to 30 carbon atoms Alkylamine group, substituted or unsubstituted C6-C30 arylamine group, substituted or unsubstituted C2-C30 heteroarylamine group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted It is selected from a ringed arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aliphatic aromatic mixed ring having 3 to 20 carbon atoms, a nitro group, a cyano group, and a halogen group.

In addition, each of R ₄₁ to R ₄₅ may be combined with one or more rings selected from the A ₁ to A ₃ rings to additionally form an alicyclic or aromatic monocyclic or polycyclic ring.

In addition, the substituents of each of the A ₁ to A ₃ rings may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

In addition, R ₄₂ and R ₄₃ and R ₄₄ and R ₄₅ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

'Substitution' in 'substituted or unsubstituted' means that each of A ₁ to A ₃ and R ₄₁ to R ₄₅ is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, or a carbon number 1 to 24 halogenated alkyl groups, cycloalkyl groups of 3 to 30 carbon atoms, alkenyl groups of 2 to 24 carbon atoms, alkynyl groups of 2 to 24 carbon atoms, heteroalkyl groups of 1 to 24 carbon atoms, aryl groups of 6 to 30 carbon atoms, 7 to 24 carbon atoms Arylalkyl group having 30 carbon atoms, alkylaryl group having 7 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 2 to 30 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, and 6 carbon atoms to 30 arylamino group, C2 to 30 heteroarylamino group, C1 to 24 alkylsilyl group, C6 to 30 arylsilyl group, C6 to 30 aryloxy group and C3 to 30 aliphatic aromatic mixture It means that it is substituted with one or more substituents selected from ring groups.

According to one embodiment of the present invention, [Formula D-1] and [Formula D-2] may be any one selected from compounds represented by the following formula, but the range is not limited thereby.

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

In addition, in the organic light emitting device according to the present invention, the dopant in the light emitting layer is a mixture or stacking of one or more other dopant compounds in addition to the one dopant compound represented by [Formula D-1] or [Formula D-2]. characterized by

As such, in the organic light emitting device according to the present invention, the light emitting layer may further include a mixture or a plurality of layers of various hosts and various dopant materials in addition to the host and the dopant according to the present invention.

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

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

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

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

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

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

As long as the hole injection layer material is commonly used in the art, it may be used without particular limitation, and as a specific example, 2-TNATA [4,4', 4"-tris (2-naphthylphenyl-phenylamino) -triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ] etc. can be used.

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

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

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

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

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

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

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

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

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

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

Synthesis Example 1. Synthesis of [43]

Synthesis Example 1-1: Synthesis of Intermediate 1-a

<Intermediate 1-a>

Bromobenzene (d5) (60.4 g, 0.373 mol) and 480 mL of tetrahydrofuran were added to a 2 L reactor, and the mixture was cooled and stirred at -78 °C. Normal butyllithium (223.6 mL, 0.357 mol) was added dropwise to the cooled reaction solution and stirred at the same temperature for 1 hour. O-phthalaldehyde (20 g, 0.149 mol) was dissolved in 100 mL of tetrahydrofuran and added dropwise to the reaction solution, followed by stirring at room temperature. After completion of the reaction, 200 mL of an aqueous ammonium chloride solution was added to terminate the reaction. The reaction solution was extracted with ethyl acetate, concentrated under reduced pressure, and separated by column chromatography to obtain <Intermediate 1-a>. (40 g, 89%)

Synthesis Example 1-2: Synthesis of Intermediate 1-b

<Intermediate 1-b>

<Intermediate 1-a> (40 g, 0.133 mol) was dissolved in 200 mL of acetic acid in a 500 mL reactor and stirred. 2 mL of hydrogen bromide was added to the reaction solution, and the mixture was stirred at 80 °C for 2 hours. After completion of the reaction, after cooling to room temperature, the reaction solution was slowly poured into a beaker containing 500 mL of distilled water and stirred. The resulting solid was filtered and washed with distilled water. The solid was separated by column chromatography to obtain <Intermediate 1-b>. (13 g, 37%)

Synthesis Example 1-3: Synthesis of Intermediate 1-c

<Intermediate 1-c>

After dissolving <Intermediate 1-b> (13.0 g, 0.049 mol) and 130 mL of N,N-dimethylamide in a 500 mL reactor, the mixture was stirred at room temperature. N-bromosuccinimide (10.54 g, 0.059 mol) was dissolved in 40 mL of N,N-dimethylamide and added dropwise to the reaction solution. The reaction was terminated by confirming the reaction by thin membrane chromatography. The reaction solution was poured into a beaker containing 500 mL of distilled water and stirred. The resulting solid was filtered and washed with distilled water. The material was separated by column chromatography to obtain <Intermediate 1-c>. (14 g, 83%)

Synthesis Example 1-4: Synthesis of Intermediate 1-d

<Intermediate 1-d>

After dissolving <Intermediate 1-c> (50 g, 0.146 mol) and 500 mL of tetrahydrofuran in a 500 mL reactor, the temperature was lowered to -78 ° C, and normal butyllithium (100 mL, 0.161 mol) was added dropwise. After stirring for 5 hours, trimethyl borate (18 mL, 0.161 mol) was added and stirred at room temperature overnight. After completion of the reaction, the mixture was acidified with 2-normal hydrochloric acid and recrystallized to obtain <Intermediate 1-d>. (25 g, 56%)

Synthesis Example 1-5: Synthesis of Intermediate 1-e

<Intermediate 1-e>

<Intermediate 1-d> (30 g, 0.098 mol), (4-bromophenyl)boronic acid (23.5 g, 0.117 mol), palladium acetate (0.4 g, 0.002 mol), potassium carbonate (27 g) in a 500 mL reactor , 0.195 mol) and Sphos (1.6 g, 0.004 mol), followed by 200 mL of toluene, 90 mL of ethanol, and 60 mL of distilled water. The temperature of the reactor was raised to 90 °C and stirred overnight. When the reaction was completed, the temperature of the reactor was lowered to room temperature, extraction was performed with methanol, and the organic layer was separated. The organic layer was concentrated under reduced pressure, separated by column chromatography, and recrystallized with toluene and acetone to obtain <Intermediate 1-e>. (12 g, 32%)

Synthesis Example 1-6: Synthesis of [43]

[43]

In Synthesis Example 1-5, <Intermediate 1-e> was used instead of <Intermediate 1-d>, and 2-bromo-3-phenylbenzofuran was used instead of (4-bromophenyl)boronic acid. [43] was obtained. (yield 30%)

MS (MALDI-TOF): m/z 531.25 [M ⁺ ]

Synthesis Example 2. Synthesis of [56]

Synthesis Example 2-1: Synthesis of Intermediate 2-a

<Intermediate 2-a>

In a 500 mL reactor, 5-bromobenzofuran (30 g, 0.152 mol), (phenyl-d5)boronic acid (23.2 g, 0.183 mol), tetrakis(triphenylphosphine)palladium(0) (5.3 g, 0.005 mol), potassium carbonate (42.1 g, 0.305 mol), 300 mL of THF, and 120 mL of distilled water were added and stirred under reflux for 12 hours. After completion of the reaction, the reactants were layer-separated, and the organic layer was concentrated under reduced pressure and separated by column chromatography to obtain <Intermediate 2-a>. (21.2 g, 70%)

Synthesis Example 2-2: Synthesis of Intermediate 2-b

<Intermediate 2-b>

<Intermediate 2-a> (21.2g, 0.106mol) and dichloromethane were added to a 500 mL reactor, cooled to -10 °C, and then bromine was added and stirred for 1 hour. An aqueous solution of sodium thiosulfate was added to the reaction solution, and after stirring, the layers were separated and the organic layer was concentrated under reduced pressure. Ethanol was added thereto and cooled to -10 ° C. After dissolving potassium hydroxide in ethanol, the mixture was heated and refluxed for 4 hours. After completion of the reaction, the reactants were sufficiently separated, and the organic layer was concentrated under reduced pressure and separated by column chromatography to obtain <Intermediate 2-b>. (20 g, 70%)

Synthesis Example 2-3: Synthesis of [56]

[56]

<Intermediate 2-b> (20 g, 0.072 mol), 10-phenyl-anthracene-9-boronic acid (25.7 g, 0.086 mol), tetrakis (triphenylphosphine) palladium (0) (2.5 g, 0.002 mol ), potassium carbonate (29.8 g, 0.216 mol), 140 mL of toluene, 60 mL of ethanol, and 60 mL of distilled water were added and refluxed for 12 hours. After completion of the reaction, the reactants were layer-separated, and the organic layer was concentrated under reduced pressure, separated and recrystallized by column chromatography to obtain [56]. (10 g, 32%)

MS (MALDI-TOF): m/z 451.20 [M ⁺ ]

Synthesis Example 3. Synthesis of [58]

Synthesis Example 3-1: Synthesis of Intermediate 3-a

<Intermediate 3-a>

<Intermediate 3-a> was obtained in the same manner as in Synthesis Example 2-1, using phenylboronic acid instead of (phenyl-d5)boronic acid. (Yield 77%)

Synthesis Example 3-2: Synthesis of Intermediate 3-b

<Intermediate 3-b>

In Synthesis Example 2-2, <Intermediate 3-a> was used instead of <Intermediate 2-a> to obtain <Intermediate 3-b> in the same manner. (70% yield)

Synthesis Example 3-3: Synthesis of Intermediate 3-c

<Intermediate 3-c>

In Synthesis Example 2-3, <Intermediate 3-b> and 4-(10-phenyl-9-anthryl)phenylboronic acid were used instead of <Intermediate 2-b> and 10-phenyl-anthracene-9-boronic acid. Thus, <Intermediate 3-c> was obtained in the same manner. (Yield 74%)

Synthesis Example 3-4: Synthesis of Intermediate 3-d

<Intermediate 3-d>

<Intermediate 3-c> (20 g, 0.038 mol) and 250 mL of THF were added to a 500 mL reactor, cooled to -50 °C, and n-butyllithium (1.6 M) was added. After 1 hour, slowly add iodine and slowly raise the temperature to room temperature. After adding an aqueous solution of sodium thiosulfate at room temperature, the layers were separated, and the organic layer was concentrated under reduced pressure and separated by column chromatography to obtain <Intermediate 3-d> (16 g, 65%)

Synthesis Example 3-5: Synthesis of [58]

[58]

In Synthesis Example 2-3, [58] was prepared in the same manner using <Intermediate 3-d> and (phenyl-d5)boronic acid instead of <Intermediate 2-b> and 10-phenyl-anthracene-9-boronic acid. got it (yield 50%)

MS (MALDI-TOF): m/z 603.26 [M ⁺ ]

synthesis example 4. [ 61] synthesis

Synthesis Example 4-1: Synthesis of Intermediate 4-a

<Intermediate 4-a>

<Intermediate 4-a> was obtained in the same manner as in Synthesis Example 2-3, using 4-bromophenyl boronic acid instead of 10-phenyl-anthracene-9-boronic acid. (Yield 71%)

Synthesis Example 4-2: Synthesis of [61]

[61]

In Synthesis Example 2-3, using <Intermediate 4-a> and 10-phenyl(d5)-anthracene-9-boronic acid instead of <Intermediate 2-b> and 10-phenyl-anthracene-9-boronic acid, the same method [61] was obtained. (yield 30%)

MS (MALDI-TOF): m/z 532.26 [M ⁺ ]

Synthesis Example 5. Synthesis of [66]

Synthesis Example 5-1: Synthesis of [66]

[66]

In Synthesis Example 2-3, 3-bromo-2-naphthalen-1-ylbenzofuran and 10-phenyl(d5)-anthracene- [66] was obtained in the same manner using 9-boronic acid. (yield 30%)

MS (MALDI-TOF): m/z 501.21 [M ⁺ ]

Synthesis Example 6. Synthesis of [14]

Synthesis Example 6-1: Synthesis of Intermediate 6-a

<Intermediate 6-a>

7-Chlorobenzo[b]thiophene (30 g, 0.178 mol) and DMF were put in a 500 mL reactor, and after stirring, NBS was added, and after reflux stirring for 6 hours, distilled water was added. The layers were separated, and the organic layer was concentrated under reduced pressure, followed by column chromatography to obtain <Intermediate 6-a> (27 g, 62%).

Synthesis Example 6-2: Synthesis of Intermediate 6-b

<Intermediate 6-b>

In Synthesis Example 2-1, <Intermediate 6-a> and phenylboronic acid were used instead of 5-bromobenzofuran and (phenyl-d5)boronic acid to obtain <Intermediate 6-b> in the same manner. (70% yield)

Synthesis Example 6-3: Synthesis of Intermediate 6-c

<Intermediate 6-c>

<Intermediate 6-c> was obtained in the same manner as in Synthesis Example 3-4, using <Intermediate 6-b> instead of <Intermediate 3-c>. (70% yield)

Synthesis Example 6-4: Synthesis of Intermediate 6-d

<Intermediate 6-d>

In Synthesis Example 2-3, using <Intermediate 6-c> and 10-phenyl(d5)-anthracene-9-boronic acid instead of <Intermediate 2-b> and 10-phenyl-anthracene-9-boronic acid, the same <Intermediate 6-d> was obtained by the method. (yield 68%)

Synthesis Example 6-5: Synthesis of [14]

[14]

In Synthesis Example 2-3, using <Intermediate 6-d> and dibenzo[b,d]furan-1-yl boronic acid instead of <Intermediate 2-b> and 10-phenyl-anthracene-9-boronic acid [14] was obtained in the same way. (yield 33%)

MS (MALDI-TOF): m/z 633.22 [M ⁺ ]

Synthesis Example 7. Synthesis of [89]

Synthesis Example 7-1: Synthesis of Intermediate 7-a

<Intermediate 7-a>

<Intermediate 7-a> in the same manner as in Synthesis Example 3-3, using 10-(phenyl-d5)-anthracene-9-boronic acid instead of 4-(10-phenyl-9-anthryl)phenylboronic acid. got (70% yield)

Synthesis Example 7-2: Synthesis of Intermediate 7-b

<Intermediate 7-b>

In Synthesis Example 3-4, <Intermediate 7-a> was used instead of <Intermediate 3-c> to obtain <Intermediate 7-b> in the same manner. (yield 63%)

Synthesis Example 7-3: Synthesis of [89]

[89]

[89] was obtained in the same manner as in Synthesis Example 3-5, using <Intermediate 7-b> and phenylboronic acid instead of <Intermediate 3-d> and (phenyl-d5)boronic acid. (yield 51%)

MS (MALDI-TOF): m/z 527.23 [M ⁺ ]

Synthesis Example 8. Synthesis of [90]

Synthesis Example 8-1: Synthesis of Intermediate 8-a

<Intermediate 8-a>

<Intermediate 8-a> was obtained in the same manner as in Synthesis Example 1-4, using (anthracene-d8)-9-bromo-10-(phenyl-d5) instead of <Intermediate 1-c>. (yield 55%)

Synthesis Example 8-2: Synthesis of Intermediate 8-b

<Intermediate 8-b>

<Intermediate 8-b> was obtained in the same manner as in Synthesis Example 2-3, using <Intermediate 8-a> instead of 10-phenyl-anthracene-9-boronic acid. (yield 55%)

Synthesis Example 8-3: Synthesis of Intermediate 8-c

<Intermediate 8-c>

In Synthesis Example 3-4, <Intermediate 8-b> was used instead of <Intermediate 3-c> to obtain <Intermediate 8-c> in the same manner. (yield 67%)

Synthesis Example 8-4: Synthesis of [90]

[90]

[90] was obtained in the same manner as in Synthesis Example 7-3, using <Intermediate 8-c> instead of <Intermediate 7-b>. (Yield 47%)

MS (MALDI-TOF): m/z 540.31 [M ⁺ ]

Synthesis Example 9. Synthesis of [91]

Synthesis Example 9-1: Synthesis of Intermediate 9-a

<Intermediate 9-a>

In a 500 mL reactor, bromobenzyl bromide (20 g, 0.08 mol), (phenyl-d5)boronic acid (10 g, 0.078 mol), sodium carbonate (10 g, 0.1 mol), tetrakis(triphenylphosphine)palladium After adding (0) (1.8 g, 0.002 mol), the temperature was raised to 50 °C and refluxed. After 1 hour, distilled water was added, stirred to separate the layers, and the organic layer was separated, washed with toluene after filtering, and concentrated under reduced pressure. Then separated by column chromatography to obtain <Intermediate 9-a> (16 g, 82%)

Synthesis Example 9-2: Synthesis of Intermediate 9-b

<Intermediate 9-b>

<Intermediate 9-a> (20 g, 0.08 mol) and 200 mL of THF were added to a 500 mL reactor, cooled to -78 °C, and then n-butyllithium (1.6 M) was added. In addition, trimethyl borate is slowly added and the temperature is gradually raised to room temperature. After adding 2M HCl aqueous solution and stirring for 20 minutes, the layers were separated, washed with distilled water, and the organic layer was concentrated and recrystallized with THF and Heptane to obtain <Intermediate 9-b> (11 g, 63%)

Synthesis Example 9-3: Synthesis of Intermediate 9-c

<Intermediate 9-c>

<Intermediate 9-b> (15 g, 0.07 mol), cesium carbonate (34 g, 0.1 mol), tetrakis (triphenylphosphine) palladium (0) (2.4 g, 0.002 mol), toluene 150 in a 500 mL reactor After adding mL, stir. After adding 1,1'-(biphenyl-d5)-2-carbonyl chloride (20 g, 0.09 mol) dropwise, the temperature was raised to 110 °C and refluxed. After 2 hours, toluene and distilled water were added, stirred to separate the layers, and the organic layer was separated, concentrated under reduced pressure, and separated by column chromatography to obtain <Intermediate 9-c> (14 g, 57%)

Synthesis Example 9-4: Synthesis of Intermediate 9-d

<Intermediate 9-d>

<Intermediate 9-c> (20 g, 0.06 mol), In(OTf)3 (3.1 g, 0.006 mol), and 120 mL of dichlorobenzene were added to a 500 mL reactor, and then the temperature was raised to 110 °C and refluxed. After 24 hours, the mixture was washed with MC after a Celite filter at 50 °C, and the organic layer was separated, concentrated under reduced pressure, and separated by column chromatography. After that, recrystallization was performed to obtain <Intermediate 9-d> (8 g, 43%)

Synthesis Example 9-5: Synthesis of Intermediate 9-e

<Intermediate 9-e>

<Intermediate 9-d> (30 g, 0.09 mol) and 300 mL of DMF were added to a 500 mL reactor, stirred, cooled to 0 ° C, NBS (16 g, 0.09 mol) was added, and the temperature was raised to room temperature and stirred. After 3 hours, distilled water was added, stirred, filtered, washed, and separated by column chromatography. After that, recrystallization was performed with methanol to obtain <Intermediate 9-e> (33 g, 89%)

Synthesis Example 9-6: Synthesis of Intermediate 9-f

<Intermediate 9-f>

In Synthesis Example 1-4, <Intermediate 9-e> was used instead of <Intermediate 1-c> to obtain <Intermediate 9-f> in the same manner. (yield 53%)

Synthesis Example 9-7: Synthesis of [91]

[91]

[91 ] was obtained. (yield 52%)

MS (MALDI-TOF): m/z 531.25 [M ⁺ ]

Synthesis Example 10. Synthesis of [92]

Synthesis Example 10-1: Synthesis of Intermediate 10-a

<Intermediate 10-a>

In Synthesis Example 1-4, <Intermediate 10-a> was obtained in the same manner using (anthracene-d8)-9-bromo-10-(1,1-biphenyl) instead of <Intermediate 1-c>. . (yield 52%)

Synthesis Example 10-2: Synthesis of Intermediate 10-b

<Intermediate 10-b>

<Intermediate 10-b> was obtained in the same manner as in Synthesis Example 2-3, using <Intermediate 10-a> instead of 10-phenyl-anthracene-9-boronic acid. (Yield 54%)

Synthesis Example 10-3: Synthesis of Intermediate 10-c

<Intermediate 10-c>

<Intermediate 10-c> was obtained in the same manner as in Synthesis Example 3-4, using <Intermediate 10-b> instead of <Intermediate 3-c>. (yield 64%)

Synthesis Example 10-4: Synthesis of [92]

[92]

[92] was obtained in the same manner as in Synthesis Example 7-3, using <Intermediate 8-c> instead of <Intermediate 7-b>. (yield 45%)

MS (MALDI-TOF): m/z 611.31 [M ⁺ ]

Examples 1 to 10: Manufacturing of organic light emitting device

The ITO glass was patterned so that the light emitting area had a size of 2 mm x 2 mm, and then washed. After mounting the ITO glass in a vacuum chamber, the base pressure was set to 1 ⅹ 10 ⁻⁷ torr, and then DNTPD (700 Å) and α-NPD (300 Å) were formed on the ITO in this order. As the light emitting layer, a film (300 Å) was formed by mixing the host compound according to the present invention and the dopant compound (3 wt%) shown in Table 1 below, and then [E-1] and [E-2] were used as electron transport layers. (300 Å) at a ratio of (1:1), [E-2] (10 Å) as an electron injection layer, and Al (1,000 Å) in this order to prepare an organic light emitting device. The emission characteristics of the organic light emitting device were measured at 10 mA/cm ² .

[DNTPD] [α-NPD] [D-102]

[E-1] [E-2]

Comparative Examples 1 to 6

Except for using [BH1] to [BH6] instead of the compounds used as the host in the above examples, an organic light emitting device was fabricated in the same manner, and the emission characteristics of the organic light emitting device were measured at 10 mA/cm ² . The structures of [BH1] to [BH6] are as follows.

[BH1] [BH2] [BH3]

[BH4] [BH5] [BH6]

division host dopant Current density (mA/cm ² ) Voltage (V) life span
(T97, hr) Example 1 [14] D-102 10 3.5 73 Example 2 [43] D-102 10 3.5 110 Example 3 [56] D-102 10 3.4 93 Example 4 [58] D-102 10 3.3 86 Example 5 [61] D-102 10 3.3 128 Example 6 [66] D-102 10 3.4 113 Example 7 [89] D-102 10 3.3 120 Example 8 [90] D-102 10 3.4 147 Example 9 [91] D-102 10 3.5 127 Example 10 [92] D-102 10 3.4 138 Comparative Example 1 BH1 D-102 10 3.6 55 Comparative Example 2 BH2 D-102 10 3.4 42 Comparative Example 3 BH3 D-102 10 3.5 50 Comparative Example 4 BH4 D-102 10 3.6 34 Comparative Example 5 BH5 D-102 10 3.9 35 Comparative Example 6 BH6 D-102 10 4.0 47

As shown in [Table 1], the device employing the compound according to the present invention as a host compound for the light emitting layer in the organic light emitting device is a compound having a difference compared to the characteristic structure of the compound according to the present invention (Comparative Examples 1 to 6) It is possible to implement a long-life, low-voltage organic light emitting device with remarkably improved lifespan characteristics compared to a device employing the.

Claims (15)

An anthracene derivative represented by the following [Formula A-1] or [Formula A-2]:
[Formula A-1] [Formula A-2]

In [Formula A-1] and [Formula A-2],
Ar ₁₁ 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; ego,
R ₂₁ to R ₃₃ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted carbon number. An alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, substituted or unsubstituted Ringed heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms Group, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 6 to 50 carbon atoms, substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, substituted or unsubstituted carbon atoms Arylamine group having 6 to 50 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring having 3 to 50 carbon atoms any one selected from a group, a cyano group, a nitro group, and a halogen group;
However, in each of [Formula A-1] and [Formula A-2], at least one of R ₂₉ to R ₃₃ is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted 3 carbon atoms It is any one selected from a cycloalkyl group of 20 to 20 and a substituted or unsubstituted heteroaryl group of 3 to 20 carbon atoms,
X is an oxygen atom (O) or a sulfur atom (S),
L ₂ is a divalent linking group, and is a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms. Any one selected from aliphatic aromatic mixed ring groups,
m is an integer from 1 to 3, and when m is 2 or more, a plurality of L ₂ are the same as or different from each other;
'Substitution' in 'substituted or unsubstituted' means that each of Ar ₁₁ , R ₂₁ to R ₃₃ and L ₂ is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group, a halogenated alkyl group, a cycloalkyl group, Alkenyl group, alkynyl group, heteroalkyl group, aryl group, arylalkyl group, alkylaryl group, heteroaryl group, heteroarylalkyl group, alkoxy group, alkylamino group, arylamino group, heteroarylamino group, alkylsilyl group, arylsilyl group, aryloxy group It means that it is substituted with one or more substituents selected from groups and aliphatic aromatic mixed ring groups,
[Formula A-1] and [Formula A-2] each contain at least one deuterium atom (D). According to claim 1,
At least one of R ₂₉ to R ₃₃ in [Formula A-1] and [Formula A-2] is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms including at least one deuterium substituent, a substituted Or an anthracene derivative characterized in that it is an unsubstituted cycloalkyl group having 3 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms. According to claim 2,
R ₂₉ in [Formula A-1] and [Formula A-2] is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted aryl group having 3 to 20 carbon atoms containing at least one deuterium as a substituent. An anthracene derivative characterized in that it is a cycloalkyl group or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms. According to claim 1,
An anthracene derivative, characterized in that the degree of deuteration of the anthracene derivative represented by [Formula A-1] or [Formula A-2] is 10% or more. According to claim 1,
An anthracene derivative, characterized in that the degree of deuteration of the anthracene derivative represented by [Formula A-1] or [Formula A-2] is 30% or more. According to claim 1,
The anthracene derivative represented by [Formula A-1] or [Formula A-2] has a degree of deuteration of 50% or more. According to claim 1,
An anthracene derivative represented by [Formula A-1] or [Formula A-2] is any one of the following [1] to [104]:

a first electrode; a second electrode opposed to the first electrode; And an organic layer interposed between the first electrode and the second electrode; includes,
An organic light emitting device in which the organic layer includes at least one anthracene derivative represented by [Formula A-1] or [Formula A-2] according to claim 1. According to claim 8,
The organic layer includes at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer, and a functional layer having both an electron injection function and an electron transport function. An organic light emitting device comprising: According to claim 8,
The organic layer interposed between the first electrode and the second electrode includes a light emitting layer, the light emitting layer is composed of a host and a dopant, and the anthracene derivative represented by [Formula A-1] or [Formula A-2] An organic light emitting device characterized in that used as a host. According to claim 10,
The light emitting layer is an organic light emitting device, characterized in that one or more other host compounds in addition to the anthracene derivative host represented by [Formula A-1] or [Formula A-2] are mixed or laminated. According to claim 10,
The dopant is an organic light emitting device, characterized in that represented by the following [Formula D-1] or [Formula D-2]:
[Formula D-1] [Formula D-2]

In [Formula D-1] and [Formula D-2],
X ₁ is any one selected from B, P=O and P=S;
Y ₁ to Y ₃ are each independently NR ₄₁ , CR ₄₂ R ₄₃ , O, S, Se and SiR ₄₄ R ₄₅ is any one selected from
A ₁ to A ₃ are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms, and Any one selected from substituted or unsubstituted aliphatic aromatic mixed rings having 3 to 30 carbon atoms,
Wherein R ₄₁ to R ₄₅ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted carbon atom group. Cycloalkyl group having 3 to 30 carbon atoms, 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 alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted An unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylthio group having 1 to 30 carbon atoms Alkylamine group, substituted or unsubstituted C6-C30 arylamine group, substituted or unsubstituted C2-C30 heteroarylamine group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted Any one selected from a cyclic arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aliphatic aromatic mixed ring having 3 to 20 carbon atoms, a nitro group, a cyano group, and a halogen group,
The R ₄₁ to R ₄₅ may be bonded to any one or more rings selected from the A ₁ to A ₃ rings to additionally form an alicyclic or aromatic monocyclic or polycyclic ring;
The substituents of each of the A ₁ to A ₃ rings may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
R ₄₂ and R ₄₃ and R ₄₄ and R ₄₅ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring;
'Substitution' in 'substituted or unsubstituted' means that each of A ₁ to A ₃ and R ₁ to R ₅ is deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group, a halogenated alkyl group, a cycloalkyl group, Alkenyl group, alkynyl group, heteroalkyl group, aryl group, arylalkyl group, alkylaryl group, heteroaryl group, heteroarylalkyl group, alkoxy group, alkylamino group, arylamino group, heteroarylamino group, alkylsilyl group, arylsilyl group, aryloxy group It means that it is substituted with one or more substituents selected from groups and aliphatic and aromatic mixed ring groups. According to claim 10,
An organic light emitting device, characterized in that the dopant in the light emitting layer is a mixture or stacking of one or more other dopant compounds in addition to the one dopant compound represented by [Formula D-1] or [Formula D-2]. According to claim 9,
At least one layer selected from the respective layers is an organic light emitting device, characterized in that formed by a deposition process or a solution process. According to claim 8,
The organic light emitting diode may include a flat panel display device; flexible display devices; devices for monochromatic or white flat lighting; and monochromatic or white flexible lighting devices; vehicle display devices; And a display device for virtual or augmented reality; organic light emitting device characterized in that used in any one device selected from.