KR20230083117A - Novel Organic compounds and Organic light emitting diode including the same - Google Patents

Abstract

The present invention relates to an organic light emitting compound which is represented by chemical formula A and can be used in an organic light-emitting device, and an organic light emitting device including the same, wherein chemical formula A is the same as described in the detailed description of the invention.

Description

Novel organic compounds and organic light emitting devices containing them {Novel Organic compounds and Organic light emitting diode including the same}

The present invention relates to a novel compound that can be used in an organic light emitting device, and more particularly, can be used as a host material for a light emitting layer in an organic light emitting device, thereby realizing high luminous efficiency and long lifespan device characteristics. It relates to a heterocyclic compound and an organic light emitting device including the same.

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows. Such an organic light emitting device is known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.

Materials used as the organic layer in the organic light emitting device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their functions. The light emitting materials can be classified into high molecular weight and low molecular weight according to molecular weight, and can be classified into fluorescent materials derived from singlet excited states of electrons and phosphorescent materials derived from triplet excited states of electrons according to light emitting mechanisms. .

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

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

Recently, as a host compound in the light emitting layer, a heterocyclic compound has been studied, and as a prior art related thereto, Patent Publication No. 10-2016-0089693 (July 28, 2016) has a structure in which a dibenzofuran ring is bonded to an anthracene ring. A compound and an organic light emitting device including the same are described, and in Patent Publication No. 10-2017-0055743 (May 22, 2017), an aryl in a condensed fluorene ring containing heteroatoms such as oxygen, nitrogen, and sulfur A compound to which a substituent or a heteroaryl substituent is bonded and an organic light emitting device including the same are disclosed.

However, despite the fact that various types of compounds for use in the light emitting layer of organic light emitting devices, including the prior art, have been prepared, new compounds that are still applicable to organic light emitting devices and have high efficiency and long lifespan device characteristics and these The need for the development of an organic light emitting device including the present situation is continuously required.

Publication No. 10-2016-0089693 (2016.07.28) Publication No. 10-2017-0055743 (2017.05.22)

Therefore, the first technical problem to be achieved by the present invention is to provide a novel organic compound that can be used as a host material for a light emitting layer in an organic light emitting device.

In addition, the second technical problem to be achieved by the present invention is to provide an organic light emitting diode (OLED) with high efficiency and long lifespan by applying the organic compound to a host material in the organic light emitting device.

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

[Formula A]

[Structural Formula A]

In the above [Formula A],

R ₁ to R ₁₂ are the same or different, and independently of each other, hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted An alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms Any one selected from;

However, at least one of R ₁ to R ₁₂ is a single bond connected to the linking group L in [Formula A], and binds the chrysene ring in Formula A with Formula A;

In the above [structural formula A],

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

Wherein n is an integer from 0 to 3, when n is 2 or more, each linking group L is the same as or different from each other,

R ₁₃ to R ₁₈ are the same or different, and independently of each other, hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted An alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms Any one selected from, wherein one of R ₁₃ to R ₁₈ is a single bond connected to the linking group L,

The R ₁₃ to R ₁₈ may be linked to groups adjacent to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,

In [Formula A] and [Structural Formula A], 'substitution' in 'substituted or unsubstituted' 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 group, C1-24 alkenyl group, C1-24 alkynyl group, C3-24 cycloalkyl group, C1-24 heteroalkyl group, C6-24 aryl group, C7-24 aryl Alkyl group, C7-24 alkylaryl group, C2-24 heteroaryl group, C2-24 heteroarylalkyl group, C1-24 alkoxy group, C1-24 alkylamino group, C12-24 carbon atom group Diarylamino group, C2-24 diheteroarylamino group, C7-24 aryl (heteroaryl) amino group, C1-24 alkylsilyl group, C6-24 arylsilyl group, C6-24 aryl It means that it is substituted with one or more substituents selected from the group consisting of an oxy group and an arylthionyl group having 6 to 24 carbon atoms.

When the novel organic compound represented by Formula A according to the present invention is used as a host material in an organic light emitting device, an organic light emitting device exhibiting higher efficiency and longer lifespan than conventional organic light emitting devices can be provided. .

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

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

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

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

The present invention provides an organic light emitting compound represented by the following [Formula A].

[Formula A]

[Structural Formula A]

In the above [Formula A],

R ₁ to R ₁₂ are the same or different, and independently of each other, hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted An alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms Any one selected from;

However, at least one of R ₁ to R ₁₂ is a single bond connected to the linking group L in [Formula A], and binds the chrysene ring in Formula A with Formula A;

In the above [structural formula A],

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

Wherein n is an integer from 0 to 3, when n is 2 or more, each linking group L is the same as or different from each other,

R ₁₃ to R ₁₈ are the same or different, and independently of each other, hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted An alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms Any one selected from, wherein one of R ₁₃ to R ₁₈ is a single bond connected to the linking group L,

The R ₁₃ to R ₁₈ may be linked to groups adjacent to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,

In [Formula A] and [Structural Formula A], 'substitution' in 'substituted or unsubstituted' 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 group, C1-24 alkenyl group, C1-24 alkynyl group, C3-24 cycloalkyl group, C1-24 heteroalkyl group, C6-24 aryl group, C7-24 aryl Alkyl group, C7-24 alkylaryl group, C2-24 heteroaryl group, C2-24 heteroarylalkyl group, C1-24 alkoxy group, C1-24 alkylamino group, C12-24 carbon atom group Diarylamino group, C2-24 diheteroarylamino group, C7-24 aryl (heteroaryl) amino group, C1-24 alkylsilyl group, C6-24 arylsilyl group, C6-24 aryl It means that it is substituted with one or more substituents selected from the group consisting of an oxy group and an arylthionyl group having 6 to 24 carbon atoms.

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

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

Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group, aromatic groups such as a pyrenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylene group, a chrysenyl group, a naphthacenyl group, a fluoranthenyl group, and the like, wherein at least one hydrogen atom in the aryl group is deuterium atom, halogen atom, hydroxyl group, nitro group, cyano group, silyl group, amino group (-NH ₂ , -NH(R), -N(R')(R''), R' and R" are each independently a carbon number An alkyl group of 1 to 10, in this case referred to as "alkylamino group"), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a carbon number It may be substituted with 2 to 24 heteroarylalkyl groups.

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

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

An alkyl group, which is a substituent used in the present invention, is a substituent in which one hydrogen is removed from an alkane, and has a structure including a straight chain type and a branched type, and specific examples thereof include methyl, ethyl, propyl, isopropyl, isobutyl, sec -butyl, tert-butyl, pentyl, iso-amyl, hexyl and the like, and at least one hydrogen atom in the alkyl group may be substituted with the same substituents as in the case of the aryl group.

'Cyclo' in the cycloalkyl group, which is a substituent used in the compound of the present invention, means a substituent having a structure capable of forming a single ring or multiple rings of saturated hydrocarbons in the alkyl group, and specific examples of the cycloalkyl group include cyclopropyl, cyclo butyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decahydronaphthyl, norbornyl, bornyl, isobornyl and the like. One or more hydrogen atoms in the cycloalkyl group may be substituted with the same substituents as in the case of the aryl group.

The alkoxy group, which is a substituent used in the compound of the present invention, is a substituent in which an oxygen atom is bonded to the terminal of an alkyl group or cycloalkyl group, and specific examples thereof include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso -amyloxy, hexyloxy, cyclobutyloxy, cyclopentyloxy, adamantaneoxy, dicyclopentanoxy, bornyloxy, isobornyloxy, etc., wherein at least one hydrogen atom in the alkoxy group is the aryl group It can be substituted with the same substituent as in the case of

Specific examples of the arylalkyl group, which is a substituent used in the compound of the present invention, include phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl and naphthylethyl, and the like, and at least one hydrogen atom in the arylalkyl group is the aryl It can be substituted with the same substituent as in the case of a group.

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

Further, in the present invention, an alkenyl group refers to an alkyl substituent including one carbon-carbon double bond formed by two carbon atoms, and an alkynyl group is formed by one carbon atom formed by two carbon atoms. means an alkyl substituent containing a carbon-carbon triple bond.

In addition, the alkylene group used in the present invention is an organic radical derived by removing two hydrogens from an alkane molecule, which is a linear or branched saturated hydrocarbon, and a specific example of the alkylene group is a methylene group , ethylene group, propylene group, isopropylene group, isobutylene group, sec-butylene group, tert-butylene group, pentylene group, iso-amylene group, hexylene group, etc., and at least one hydrogen of the alkylene group Each atom can be substituted with a substituent similar to that of the aryl group.

In the present invention, the diarylamino group refers to an amine group in which two identical or different aryl groups described above are bonded to a nitrogen atom, and a diheteroarylamino group in the present invention refers to an amine group in which two identical or different heteroaryl groups are bonded to a nitrogen atom. group, and the aryl (heteroaryl) amino group refers to an amine group in which the aryl group and the heteroaryl group are bonded to a nitrogen atom, respectively.

On the other hand, as a more preferred example of 'substitution' in the 'substituted or unsubstituted' in [Formula A], this is a deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 12 carbon atoms, a carbon number Halogenated alkyl group of 1 to 12, alkenyl group of 2 to 12 carbon atoms, alkynyl group of 2 to 12 carbon atoms, cycloalkyl group of 3 to 12 carbon atoms, heteroalkyl group of 1 to 12 carbon atoms, aryl group of 6 to 18 carbon atoms, 7 carbon atoms to 20 arylalkyl group, C7 to 20 alkylaryl group, C2 to 18 heteroaryl group, C2 to 18 heteroarylalkyl group, C1 to 12 alkoxy group, C1 to 12 alkylamino group, carbon number Diarylamino group having 12 to 18 carbon atoms, diheteroarylamino group having 2 to 18 carbon atoms, aryl (heteroaryl) amino group having 7 to 18 carbon atoms, alkylsilyl group having 1 to 12 carbon atoms, arylsilyl group having 6 to 18 carbon atoms, 6 carbon atoms It may be substituted with one or more substituents selected from the group consisting of an aryloxy group of 18 to 18 and an arylthionyl group of 6 to 18 carbon atoms.

In the present invention, the organic light-emitting compound represented by [Formula A] has at least one linking group (L)n bonded to a substituted or unsubstituted chrysene ring, and the linking group (L)n is substituted or unsubstituted benzene. By including a structure in which a furan substituent is bonded, it is characterized in that at least one substituent represented by structural formula A is bonded to a substituted or unsubstituted chrysene ring.

[Formula A]

[Structural Formula A]

As an embodiment of the present invention, at least one of the substituents R _{2 ,} R ₆ , R ₈ and R ₁₂ in the chrysene ring of [Formula A] may be a single bond bonded to the linking group L in the structural formula A. That is, at least one of the substituents R _{2 ,} R ₆ , R ₈ and R ₁₂ in the chrysene ring of [Formula A] is a single bond bonded to Structural Formula A, and the organic light emitting compound according to the present invention is a substituted or unsubstituted The linking group L may be bonded to a specific position in the chrysene ring (see structural formula C-1 below), and preferably, at least one of the substituents R ₆ and R ₁₂ is a single bond bonded to the linking group L in the structural formula A. can

[Structural Formula C-1]

*: Binding site that binds to the linking group L

In addition, as an embodiment of the present invention, the substituent R ₆ in the chrysene ring of Formula A is a single bond bonded to the linking group L in the structural formula A, or the substituent R ₈ is a single bond bonded to the linking group L in the structural formula A. bond, or R ₆ and R ₈ may be a single bond simultaneously bonded to the linking group L in the above structural formula A, and thus the organic light emitting compound according to the present invention may be a specific position in the substituted or unsubstituted chrysene ring (below The linking group L may be bonded to Structural Formula C-2 and Structural Formula C-3).

[Structural Formula C-2] [Structural Formula C-3]

*: Binding site that binds to the linking group L

As an embodiment of the present invention, the substituent R ₆ in the chrysene ring of Formula A is a single bond bonded to the linking group L in Formula A, and the substituents R _{2 ,} R ₈ and R ₁₂ are each the same as or different from each other. and may be any one selected from hydrogen, heavy hydrogen, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, independently of each other. That is, in the organic light emitting compound represented by [Formula A], the linking group L is bonded to a specific position (see Structural Formula C-4 below) in the substituted or unsubstituted chrysene ring, and at the same time, another chrysene ring Any one substituent selected from hydrogen, deuterium, substituted or unsubstituted aryl group having 6 to 18 carbon atoms and substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms at another specific position (see structural formula C-4 below) can be combined.

[Structural Formula C-4]

*: Binding site that binds to the linking group L

**: Binding site where hydrogen, deuterium, aryl group or heteroaryl group binds

More preferably in this case, the substituent R ₆ in Formula A is a single bond bonded to the linking group L in Formula A, and the substituent R ₁₂ is hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms. And it may be any one selected from a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, which can be understood in more detail with reference to structural formula C-5 below.

[Structural Formula C-5]

*: Binding site that binds to the linking group L

**: Binding site where hydrogen, deuterium, aryl group or heteroaryl group binds

In addition, as an embodiment of the present invention, the substituent R ₆ in Formula A is a single bond bonded to the linking group L in Formula A, and the substituents R _{2 ,} R ₈ and R ₁₂ are each the same as or different from each other and are independent of each other. In the case of any one selected from hydrogen, heavy hydrogen, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, the substituents R _{2 ,} R ₈ and R ₁₂ At least one of may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, and preferably, the substituent R ₁₂ is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms 18 aryl group Or it may be a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In addition, as an embodiment of the present invention, the substituent R ₆ in Formula A is a single bond bonded to the linking group L in Formula A, and the substituents R _{2 ,} R ₈ and R ₁₂ are each the same as or different from each other and are independent of each other. In the case of any one selected from hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, the substituent R in the chrysene ring of Formula A At least one of _2, R ₈ and R ₁₂ may be any one selected from [Formula 1] to [Formula 5] below, and preferably, the substituent R ₁₂ is selected from [Formula 1] to [Formula 5] below It can be any one of them.

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

[Structural Formula 4] [Structural Formula 5]

In Structural Formulas 1 to 5, the carbon site of the aromatic ring is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 14 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and a substituted or unsubstituted carbon atom having 2 to 20 carbon atoms. One or more substituents selected from the group consisting of heteroaryl groups of may be bonded.

Also, as an embodiment of the present invention, the compound represented by Formula A may contain at least one deuterium.

More specifically, in the present invention, when the compound represented by Formula A contains at least one deuterium, at least one of R _{2 ,} R ₆ , R ₈ and R ₁₂ in [Formula A] is deuterium Or a substituent containing; or at least one of R ₁₃ to R ₁₈ is deuterium or a substituent containing deuterium; preferably, at least one of R ₆ and R ₁₂ is a substituent containing deuterium; Alternatively, at least one of R ₁₃ to R ₁₈ is deuterium or a substituent containing deuterium.

In addition, as an embodiment of the present invention, the substituent R ₆ in Formula A is a single bond bonded to the linking group L in Formula A, and the substituents R _{2 ,} R ₈ and R ₁₂ are each the same as or different from each other and are independent of each other. In the case of any one selected from hydrogen, heavy hydrogen, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, the linking group L may be a single bond.

In addition, as an embodiment of the present invention, at least one of R ₁₃ to R ₁₈ not connected to L in [Structural Formula A] in Formula A may not be hydrogen.

More specifically, when at least one of R ₁₃ to R ₁₈ not connected to L in [Formula A] in the compound represented by Formula A is not hydrogen, in [Formula A] not connected to L At least one of R ₁₃ to R ₁₈ may be any one selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

More preferably, in the present invention, at least one of R ₁₃ to R ₁₈ not connected to L in [Structural Formula A] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms and a substituted or unsubstituted 2 to 30 carbon atoms In the case of any one selected from a heteroaryl group of, at least one of R ₁₃ to R ₁₈ not connected to L in [Formula A] may be any one selected from [Formula 1] to [Formula 6] below. there is.

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

[Formula 4] [Formula 5] [Formula 6]

In Structural Formulas 1 to 6, the carbon site of the aromatic ring is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 14 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and a substituted or unsubstituted carbon atom having 2 to 20 carbon atoms. One or more substituents selected from the group consisting of heteroaryl groups of may be bonded.

In addition, as an embodiment according to the present invention, as a kind of preferred substituents in the substituents R ₁ to R ₁₈ , which are the same or different and independently of each other, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms , substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 15 carbon atoms, substituted or unsubstituted 6 to 18 carbon atoms It may be any one substituent selected from 20 arylsilyl groups, cyano groups, and halogen groups.

As an embodiment of the present invention, the linking group L may preferably be a single bond or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, more preferably the linking group L is a single bond, or the following [ It may be any one selected from Structural Formula 6] to [Structural Formula 10].

[Formula 6] [Formula 7] [Formula 8]

[Structural Formula 9] [Structural Formula 10]

In the linking group L, hydrogen or deuterium may be bonded to the carbon site of the aromatic ring.

In addition, as a specific example of the organic light emitting compound represented by [Formula A] according to the present invention, it may be any one compound selected from the following [A-1] to [A-115], but is not limited thereto.

[A-1][A-2][A-3]

[A-4][A-5][A-6]

[A-7][A-8][A-9]

[A-10][A-11][A-12]

[A-13][A-14][A-15]

[A-16][A-17][A-18]

[A-19][A-20][A-21]

[A-22][A-23][A-24]

[A-25][A-26][A-27]

[A-28][A-29][A-30]

[A-31][A-32][A-33]

[A-34][A-35][A-36]

[A-37][A-38][A-39]

[A-40][A-41][A-42]

[A-43][A-44][A-45]

[A-46][A-47][A-48]

[A-49][A-50][A-51]

[A-52][A-53][A-54]

[A-55][A-56][A-57]

[A-58][A-59][A-60]

[A-61][A-62][A-63]

[A-64][A-65][A-66]

[A-67][A-68][A-69]

[A-70][A-71][A-72]

[A-73][A-74][A-75]

[A-76][A-77][A-78]

[A-79][A-80][A-81]

[A-82][A-83][A-84]

[A-85][A-86][A-87]

[A-88][A-89][A-90]

[A-91][A-92][A-93]

[A-94][A-95][A-96]

[A-97][A-98][A-99]

[A-100][A-101][A-102]

[A-103][A-104][A-105]

[A-106][A-107][A-108]

[A-109][A-110][A-111]

[A-112][A-113][A-114]

[A-115]

In addition, the present invention is a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one compound represented by Formula A according to the present invention.

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 compounds represented by a host material in the light emitting layer.

In addition, as a dopant compound used in the light emitting layer in the present invention, at least one compound represented by any one of the following [Formula D1] to [Formula D10] may be included.

[Formula D1]

[Formula D2]

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

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

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

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

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

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

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

wherein x1 is 1, y1, z1 and z2 are each the same or different, and are independently integers from 0 to 1;

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

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

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

[Formula D3]

In the above [Formula D3],

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

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

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

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

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

[Formula D4] [Formula D5]

In [Formula D4] and [Formula D5],

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

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

Y4 is any one selected from N-R61, CR62R63, O, S, and SiR64R65;

Y5 is any one selected from N-R66, CR66R68, O, S, SiR69R70

Y6 is any one selected from N-R71, CR72R73, O, S, and SiR74R75;

R61 to R75 are the same as R61 to R70 in [Formula D3].

[Formula D6] [Formula D7]

X ₃ is any one selected from B, P, and P=O;

T ₇ to T ₉ are the same as T ₁ to T ₃ in [Formula D3],

Y ₆ is any one selected from N-R61, CR62R63, O, S, and SiR64R65;

The substituents R ₆₁ to R ₆₅ and R ₇₁ to R ₇₂ are each the same as R61 to R70 in [Formula D3],

R ₇₁ and R ₇₂ are linked to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, or combined with the T ₇ ring or T ₉ ring to additionally form an alicyclic or aromatic monocyclic or polycyclic ring. can do.

[Formula D8] [Formula D9]

[Formula D10]

In [Formula D8] to [Formula D10],

Wherein X is any one selected from B, P, P = O,

The Q1 to Q3 are the same as T ₁ to T ₃ in [Formula D3],

The linking group Y is any one selected from NR ₃ , CR 4 R 5 , O, S, and Se;

The substituents R3 to R5 are the same as R61 to R70 in [Formula D3], respectively,

The R ₃ to R ₅ may each be bonded to the Q ₂ ring or the Q ₃ ring to further form an alicyclic or aromatic monocyclic or polycyclic ring,

The R ₄ and R ₅ may be linked to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,

The ring formed by the Cy1 has a nitrogen (N) atom, an aromatic carbon atom in the Q1 ring to which the nitrogen (N) atom is bonded, and an aromatic carbon atom in the Q1 ring to be bonded to the Cy1, substituted or unsubstituted carbon atoms 1 to 10 alkylene groups,

In Formula D9,

'Cy2' may be added to Cy1 to form a saturated hydrocarbon ring, and the ring formed by Cy2 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, except for carbon atoms included in Cy1,

In the formula D10,

The ring formed by the Cy3 is an aromatic carbon atom in the Q3 ring to be bonded to Cy3, an aromatic carbon atom in Q3 to be bonded to a nitrogen (N) atom, a nitrogen (N) atom, and in Cy1 to which the nitrogen (N) atom is bonded. Excluding carbon atoms, it is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,

Here, 'substitution' in the 'substituted or unsubstituted' in [Formula D1] to [Formula D10] is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a carbon number 1 -24 halogenated alkyl group, C2-24 alkenyl group, C2-24 alkynyl group, C3-24 cycloalkyl group, C1-24 heteroalkyl group, C6-24 aryl group, C7-24 Arylalkyl group having 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, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, and 12 carbon atoms to 24 diarylamino group, C2 to 24 diheteroarylamino group, C7 to 24 aryl (heteroaryl) amino group, C1 to 24 alkylsilyl group, C6 to 24 arylsilyl group, C6 to 24 It means that it is substituted with one or more substituents selected from the group consisting of an aryloxy group of 24 and an arylthionyl group of 6 to 24 carbon atoms, and as a more preferred example, it is a deuterium group, a cyano group, a halogen group, a hydroxyl group, a nitro group, a carbon number Alkyl group of 1 to 12 carbon atoms, halogenated alkyl group of 1 to 12 carbon atoms, alkenyl group of 2 to 12 carbon atoms, alkynyl group of 2 to 12 carbon atoms, cycloalkyl group of 3 to 12 carbon atoms, heteroalkyl group of 1 to 12 carbon atoms, 6 to 12 carbon atoms 18 aryl group, C7-20 arylalkyl group, C7-20 alkylaryl group, C2-18 heteroaryl group, C2-18 heteroarylalkyl group, C1-12 alkoxy group, C1 to 12 alkylamino groups, carbon atoms of 12 to 18 diarylamino groups, carbon atoms of 2 to 18 diheteroarylamino groups, carbon atoms of 7 to 18 aryl (heteroaryl) amino group, carbon atoms of 1 to 12 alkylsilyl group, carbon atoms of 6 to 18 It may be substituted with one or more substituents selected from the group consisting of an arylsilyl group, an aryloxy group having 6 to 18 carbon atoms, and an arylthionyl group having 6 to 18 carbon atoms.

In addition, in the case of a boron compound represented by any one of [Formula D3] to [Formula D10] among the dopant compounds according to the present invention, the aromatic hydrocarbon ring of T1 to T9 or Q1 to Q3, or an aromatic heterocyclic ring is substituted. As possible substituents, heavy hydrogen, an alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, and an arylamino group having 6 to 24 carbon atoms may be substituted, wherein the Each of the alkyl groups or aryl groups in the alkylamino group and the C6-24 arylamino group may be linked to each other, and more preferred substituents include an alkyl group of 1 to 12 carbon atoms, an aryl group of 6 to 18 carbon atoms, and an alkylamino group of 1 to 12 carbon atoms. , An arylamino group having 6 to 18 carbon atoms may be substituted, and each alkyl group or aryl group in the alkylamino group having 1 to 12 carbon atoms and the arylamino group having 6 to 18 carbon atoms may be linked to each other.

On the other hand, as a specific example of the compound represented by any one of [Formula D1] to [Formula D2] among the dopant compounds used in the light emitting layer in the organic light emitting device according to the present invention, a compound represented by any one of d1 to d239 below can be

<d 1> <d2> <d 3>

<d 4> <d 5> <d 6>

<d 7> <d 8> <d 9>

<d 10> <d 11> <d 12>

<d 13> <d 14> <d 15>

<d 16> <d 17> <d 18>

<d 19> <d 20> <d 21>

<d 22> <d 23> <d 24>

<d 25> <d 26> <d 27>

<d 28> <d 29> <d 30>

<d 31> <d 32> <d 33>

<d 34> <d 35> <d 36>

<d 37> <d 38> <d 39>

<d 40> <d 41> <d 42>

<d 43> <d 44> <d 45>

<d 46> <d 47> <d 48>

<d 49> <d 50> <d 51>

<d 52> <d 53> <d 54>

<d 55> <d 56> <d 57>

<d 58> <d 59> <d 60>

<d 61> <d 62> <d 63>

<d 64> <d 65> <d 66>

<d 67> <d 68> <d 69>

<d 70> <d71> <d 72>

<d73> <d 74> <d 75>

<d 76> <d 77> <d 78>

<d 79> <d 80> <d 81>

<d 82> <d 83> <d 84>

<d 85> <d 86> <d 87>

<d 88> <d 89> <d 90>

<d 91> <d 92> <d 93>

<d 94> <d 95> <d 96>

<d 97> <d 98> <d 99>

<d 100 ><d 101 > <d 102>

<d 103> <d 104> <d 105>

<d 106> <d 107> <d 108>

<d 109> <d 110> <d 111>

<d 112> <d 113> <d 114>

<d 115> <d 116> <d 117>

<d 118> <d 119 > <d 120>

<d 121> <d 122> <d 123>

<d 124> <d 125> <d 126>

<d 127> <d 128> <d 129>

<d 130> <d 131> <d 132>

<d 133> <d 134> <d135>

<d 136> <d 137> <d 138>

<d 139 > <d 140> <d 141>

<d 142> <d 143> <d 144>

<d 145 > <d 146> <d 147>

<d 148> <d 149 > <d 150>

<d 151 > <d 152> <d 153>

<d 154> <d 155> <d 156>

<d 157> <d 158> <d 159>

<d 160> <d 161 > <d 162>

<d 163> <d 164> <d 165>

<d 166> <d 167> <d 168>

<d 169 > <d 170> <d 171>

<d 172> <d 173> <d 174>

<d 175 > <d 176> <d 177>

<d 178> <d 179 > <d 180>

<d 181 > <d 182> <d 183>

<d 184> <d 185> <d 186>

<d 187> <d 188> <d 189>

<d 190 > <d 191> <d 192>

<d 193> <d 194> <d 195>

<d 196> <d 197> <d 198>

<d 199 > <d 200> <d 201>

<d 202> <d 203> <d 204>

<d 205> <d 206> <d 207>

<d 208> <d 209> <d 210>

<d 211> <d 212> <d 213>

<d 214> <d 215> <d 216>

<d 217> <d 218> <d 219>

<d 220> <d 221> <d 222>

<d 223> <d 224> <d 225>

<d 226> <d 227> <d 228>

<d 229> <d 230> <d 231>

<d 232> <d 233> <d 234>

<d235> <d 236> <d 237>

<d 238> <d 239>

Further, in the present invention, the compound represented by [Formula D3] among the dopant compounds in the light emitting layer may be a compound represented by any one selected from the following <D 101> to <D 130>.

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

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

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

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

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

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

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

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

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

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

Further, in the present invention, the compound represented by any one of [Formula D4], [Formula D5], [Formula D8] to [Formula D10] among the dopant compounds in the light emitting layer is selected from the following <D201> to <D476> It may be a compound represented by any selected one.

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

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

[D 209] [D 210] [D211] [D212]

[D213] [D 214] [D 215] [D 216]

[D 217] [D218] [D219] [D 220]

[D221] [D 222] [D 223] [D 224]

[D225] [D226] [D 227] [D228]

[D 229] [D 230] [D231] [D 232]

[D233] [D 234] [D 235] [D 236]

[D237] [D238] [D 239] [D240]

[D 241] [D 242] [D 243] [D 244]

[D 245] [D 246] [D 247] [D248]

[D 249] [D 250] [D251] [D 252]

[D 253] [D 254] [D 255] [D 256]

[D 257] [D 258] [D 259] [D 260]

[D 261] [D 262] [D 263] [D 264]

[D 265] [D 266] [D 267] [D 268]

[D 269] [D 270] [D 271] [D 272]

[D 273] [D 274] [D 275] [D 276]

[D 277] [D 278] [D 279] [D 280]

[D 281] [D 282] [D 283] [D 284]

[D 285] [D 286] [D 287] [D 288]

[D 289] [D 290] [D 291] [D 292]

[D 293] [D 294] [D 295] [D 296]

[D 297] [D 298] [D 299] [D300]

[D301] [D 302] [D303] [D304]

[D 305] [D 306] [D307] [D308]

[D 309] [D 310] [D311] [D312]

[D313] [D314] [D315] [D316]

[D317] [D318] [D319] [D320]

[D321] [D322] [D323] [D324]

[D325] [D326] [D327] [D328]

[D 329] [D330] [D331] [D 332]

[D 333] [D334] [D 335] [D336]

[D337] [D338] [D 339] [D340]

[D341] [D342] [D343] [D 344]

[D 345] [D346] [D 347]

[D348] [D 349] [D 350]

[D 351] [D 352] [D 353]

[D 354] [D 355] [D 356]

[D 357] [D 358] [D 359]

[D 360] [D 361] [D 362]

[D 363] [D 364] [D 365]

[D 366] [D 367] [D 368]

[D 369] [D 370] [D 371]

[D 372] [D 373] [D 374]

[D 375] [D 376] [D 377]

[D 378] [D 379] [D 380]

[D 381] [D 382] [D 383]

[D 384] [D 385] [D 386]

[D 387] [D 388] [D 389]

[D 390] [D 391] [D 392]

[D 393] [D 394] [D 395]

[D 396] [D 397] [D 398]

[D 399] [D 400] [D 401]

[D 402] [D 403] [D 404]

[D 405] [D 406] [D 407]

[D 408] [D 409] [D 410]

[D 411] [D 412] [D 413]

[D414] [D415] [D416]

[D417] [D418] [D419]

[D420] [D421] [D422]

[D 423] [D 424] [D 425]

[D426] [D427] [D428]

[D 429] [D 430] [D 431]

[D 432] [D 433] [D 434]

[D 435] [D 436] [D 437]

[D 438] [D 439] [D 440]

[D 441] [D 442] [D 443]

[D444] [D445] [D446]

[D447] [D448] [D449]

[D450] [D451] [D452]

[D453] [D454] [D455]

[D456] [D457] [D458]

[D 459] [D460] [D461]

[D462] [D463] [D464]

[D465] [D466] [D 467]

[D468] [D 469] [D 470]

[D471] [D472] [D 473]

[D474] [D 475] [D476]

Further, in the present invention, the compound represented by any one of [Formula D6] and [Formula D7] among the dopant compounds in the light emitting layer may be a compound represented by any one selected from the following <D501> to <D587>. there is.

<D 501> <D 502> <D503>

<D 504> <D 505> <D506>

<D507> <D 508> <D509>

<D 510> <D511> <D512>

<D513> <D514> <D515>

<D516> <D517> <D 518>

<D 519> <D 520> <D 521>

\<D 522> <D 523> <D524>

<D 525> <D 526> <D 527>

<D 528> <D 529> <D 530>

<D531> <D532> <D533>

<D534> <D 535> <D536>

<D537> <D 538> <D 539>

<D 540> <D541> <D542>

<D543> <D544> <D545>

<D546> <D547> <D548>

<D 549> <D 550> <D551>

<D 552> <D553> <D 554>

<D 555> <D 556> <D 557>

<D 558> <D 559> <D 560>

<D 561> <D 562> <D 563>

<D 564> <D 565> <D 566>

<D 567> <D 568> <D 569>

<D 570> <D 571> <D 572>

<D 573> <D 574> <D 575>

<D 576> <D 577> <D 578>

<D 579> <D 580> <D 581>

<D 582> <D 583> <D 584>

<D 585> <D 586> <D 587>

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

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

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

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

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

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

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

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

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

The hole injection layer material may be used without particular limitation as long as it is commonly used in the art, and for example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ], etc. However, the present invention is not necessarily limited thereto.

In addition, the hole injection layer material may optionally be used together with a dopant.

In addition, the material of the hole transport layer 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 (a-NPD) or the like can be used. However, the present invention is not necessarily limited thereto.

Meanwhile, in the present invention, an electron blocking layer (electron blocking layer) may be additionally formed on the hole transport layer. The electron blocking layer is a layer for preventing electrons injected from the electron injection layer from entering the hole transport layer through the light emitting layer to improve the lifespan and efficiency of the device, and may be formed at an appropriate portion between the light emitting layer and the hole injection layer. And, preferably, it may be formed between the light emitting layer and the hole transport layer.

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

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

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

Meanwhile, in the present invention, a hole blocking layer may be additionally formed on the light emitting layer. The hole blocking layer is a layer for preventing holes injected from the hole injection layer from entering the electron transport layer through the light emitting layer to improve the lifespan and efficiency of the device, and may be formed at an appropriate portion between the light emitting layer and the electron transport layer. .

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

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

TAZ BAlq

<Compound 201> <Compound 202> BCP

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

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

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

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

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

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

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

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

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

(Example)

Synthesis Example 1. Synthesis of [A-1]

Synthesis Example 1-1. Synthesis of <1-a>

<1-a>

After purging with nitrogen in a round bottom flask, 50 g (0.219 mol) of chrysene and 500 ml of chloroform were added and stirred. 69.565 g (0.438 mol) of bromine was slowly added dropwise at room temperature, and after the dropwise addition was completed, the mixture was refluxed for 24 hours. After the reaction was completed, an aqueous solution of sodium thiosulfate was added, stirred, the layers were separated, and the organic layer was concentrated under reduced pressure, separated through column chromatography, and crystallized with methanol to obtain 50 g of <1-a> (yield: 74.3%).

Synthesis Example 1-2. Synthesis of [A-1]

[A-1]

In a round bottom flask in a nitrogen atmosphere, <1-a> 10 g (0.033 mol), 3-benzofuranboronic acid 5.7 g (0.036 mol), tetrakistriphenylphosphine palladium 0.8 g (0.00065 mol), potassium carbonate 9 g (0.065 mol), 100 ml of toluene and 30 ml of water were added and refluxed for 12 hours. When the reaction was completed, the reaction solution was cooled to room temperature, layer separation was performed, the organic layer was concentrated, separated using column chromatography, and 9 g of [A-1] was obtained through recrystallization. (Yield: 80%)

MS(MALDI-TOF): m/z 344.12[M]

Synthesis Example 2. Synthesis of [A-6]

[A-6]

<1-a> 10 g (0.033 mol), 2-phenyl-3-benzofuranboronic acid 8.52 g (0.036 mol), tetrakistriphenylphosphine palladium 0.8 g (0.00065 mol) in a round bottom flask in a nitrogen atmosphere , 9 g (0.065 mol) of potassium carbonate, 100 ml of toluene and 30 ml of water were added and refluxed for 12 hours. When the reaction was completed, the reaction solution was cooled to room temperature, layer separation was performed, the organic layer was concentrated, separated using column chromatography, and 11.4 g of [A-6] was obtained through recrystallization. (Yield 83.3%)

MS(MALDI-TOF) : m/z 420.15[M]

Synthesis Example 3. Synthesis of [A-14]

Synthesis Example 3-1. Synthesis of <3-a>

<3-a>

6-bromo-4-methoxy-2phenylbenzofuran was synthesized in the same manner as in Synthesis Example 1-2, except that phenylboronic acid was used instead of 3-benzofuranboronic acid in place of <1-a>. Thus, 24 g of <3-a> was obtained. (Yield 80.7%)

Synthesis Example 3-2. Synthesis of <3-b>

<3-b>

Put <3-a> 24 g (0.080 mol) and 240 ml of dichloromethane in a round bottom flask in a nitrogen atmosphere, lower it to 0 degrees in an ice bath, and then slowly add 30 g (0.120 mol) of tribromoborane. After heating to 30 ℃ and stirring for 1 hour, the reaction solution was poured into a beaker containing water. Then, after work-up, 21.2 g of <3-b> was obtained through recrystallization. (Yield: 92.7%)

Synthesis Example 3-3. Synthesis of <3-c>

<3-c>

21.2 g (0.074 mol) of <3-b> and 200 ml of dichloromethane were added to a round bottom flask under a nitrogen atmosphere, and after stirring, 11.7 g (0.148 mol) of pyridine was added to completely dissolve <3-b>. Then, the temperature was lowered to 0 ° C., and 33.4 g (0.118 mol) of trifluoromethylsulfonic anhydride was slowly added thereto. After 3 hours, add water and proceed with work-up. After removing the solvent, 30.1 g of <3-c> was obtained through a silica column. (Yield 97.2%)

Synthesis Example 3-4. Synthesis of <3-d>

<3-d>

<3-c> 30.1 g (0.072 mol), pinacol diboron 21.9 g (0.086 mol), PdCl ₂ (dppf) 2.6 g (0.004 mol), potassium acetate 13.7 g (0.144 mol) in a round bottom flask in a nitrogen atmosphere , 301 ml of dioxane was added and stirred under reflux. After 8 hours, 20.4 g of <3-d> was obtained through a celite filter, a solvent was removed, and a silica column was performed. (Yield 71.6%).

Synthesis Example 3-5. Synthesis of [A-14]

[A-14]

[A-14]

13 g of [A-14] was obtained by synthesizing in the same manner except that <3-d> was used instead of 3-benzofuranboronic acid used in Synthesis Example 1-2. (Yield 57.4%)

MS(MALDI-TOF): m/z 496.185[M]

Synthesis Example 4. Synthesis of [A-39]

Synthesis Example 4-1. Synthesis of <4-a>

<4-a>

After purging with nitrogen in a round bottom flask, 50 g (0.219 mol) of chrysene and 500 ml of chloroform were added and stirred. 87.5 g (0.548 mol) of bromine was slowly added dropwise at room temperature, and after the dropwise addition was completed, the mixture was refluxed for 24 hours. After the reaction was completed, an aqueous solution of sodium thiosulfate was added, and the layers were separated after stirring, and the organic layer was concentrated under reduced pressure and crystallized with methanol to obtain <4-a> 76 g. (Yield 89.9%)

Synthesis Example 4-2. Synthesis of <4-b>

<4-b>

<4-a> was synthesized in the same manner except that phenylboronic acid was used instead of 3-benzofuranboronic acid for <4-a> instead of <1-a> used in Synthesis Example 1-2 to obtain 43 g of <4-b> . (Yield 57%)

Synthesis Example 4-3. Synthesis of <4-c>

<4-c>

In the same manner, except that 5-bromo-7-methoxy-2-phenylbenzofuran was used instead of <1-a> used in Synthesis Example 1-2 and phenylboronic acid was used instead of 3-benzofuranboronic acid. Synthesized to obtain 35 g of <4-c>. (Yield 82.2%)

Synthesis Example 4-4. Synthesis of <4-d>

<4-d>

30 g of <4-d> was obtained in the same manner as in Synthesis Example 3-2, except that <4-c> was used instead of <3-a>. (Yield 89.9%)

Synthesis Example 4-5. Synthesis of <4-e>

<4-e>

41.2 g of <4-e> was obtained by synthesizing in the same manner except that <4-d> was used instead of <3-b> used in Synthesis Example 3-3. (Yield 94.0%)

Synthesis Example 4-6. Synthesis of <4-f>

<4-f>

27.2 g of <4-f> was obtained by synthesizing in the same manner except that <4-e> was used instead of <3-c> used in Synthesis Example 3-4. (Yield 69.7%)

Synthesis Example 4-7. Synthesis of [A-39]

[A-39]

[A-39] 12 [A-39] 12 got g. (Yield 53.5%)

MS(MALDI-TOF) : m/z 572.21[M]

Synthesis Example 5. Synthesis of [A-54]

Synthesis Example 5-1. Synthesis of <5-a>

<5-a>

Same method as in Synthesis Example 1-2, except that 4-dibenzofuranboronic acid was used instead of 5-bromo-7-methoxybenzofuran and 3-benzofuranboronic acid instead of <1-a>. 43.5 g of <5-a> was obtained. (Yield 78.6%)

Synthesis Example 5-2. Synthesis of <5-b>

<5-b>

38.6 g of <5-b> was obtained by synthesizing in the same manner except that <5-a> was used instead of <3-a> used in Synthesis Example 3-2. (Yield 92.9%)

Synthesis Example 5-3. Synthesis of <5-c>

<5-c>

50.3 g of <5-c> was obtained by synthesizing in the same manner except that <5-b> was used instead of <3-b> used in Synthesis Example 3-3. (Yield 90.5%)

Synthesis Example 5-4. Synthesis of <5-d>

<5-d>

27.2 g of <5-d> was obtained by synthesizing in the same manner except that <5-c> was used instead of <3-c> used in Synthesis Example 3-4. (Yield 69.7%)

Synthesis Example 5-5. Synthesis of [A-54]

[A-54]

[A-54] 13 [A-54] 13 got g. (Yield 54.5%)

MS(MALDI-TOF): m/z 586.19[M]

Synthesis Example 6. Synthesis of [A-92]

Synthesis Example 6-1. Synthesis of <6-a>

<6-a>

<6-a> 44 g was obtained. (yield 63%)

Synthesis Example 6-2. Synthesis of <6-b>

<6-b>

2-Bromo-4-methoxybenzofuran was synthesized in the same manner as in Synthesis Example 1-2, except that d-5phenylboronic acid was used instead of 3-benzofuranboronic acid in place of <1-a>. Thus, 32 g of <6-b> was obtained. (Yield 72%)

Synthesis Example 6-3. Synthesis of <6-c>

<6-c>

28.5 g of <6-c> was obtained by synthesizing in the same manner except that <6-b> was used instead of <3-a> used in Synthesis Example 3-2. (Yield 94.9%)

Synthesis Example 6-4. Synthesis of <6-d>

<6-d>

41.2 g of <6-d> was obtained by synthesizing in the same manner except that <6-c> was used instead of <3-b> used in Synthesis Example 3-3. (Yield 89..5%)

Synthesis Example 6-5. Synthesis of <6-e>

<6-e>

30.1 g of <6-e> was obtained by synthesizing in the same manner except that <6-d> was used instead of <3-c> used in Synthesis Example 3-4. (Yield 78%)

Synthesis Example 6-5. Synthesis of [A-92]

[A-92]

[A-92] 15 [A-92] 15 got g. (Yield 62.3%)

MS(MALDI-TOF) : m/z 506.25[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, as a hole injection layer on the ITO, electron acceptors [Acceptor-1] and [Formula F] of the following structural formula were deposited at a deposition rate A film (100 Å) was formed by performing binary deposition at a deposition rate of [Acceptor-1] : [Formula F] = 2 : 98. [Formula F] was formed as a hole transport layer (550 Å), and then [Formula G] was formed as a film (50 Å) as an electron blocking layer. The light emitting layer is formed by mixing the compound of the present invention and the dopant [BD-1] (2 wt%) described below to form a film (200 Å), and then forming a film (50 Å) of [Formula H] as a hole blocking layer , [Formula E-1] and [Formula E-2] as an electron transport layer, 250 Å at a ratio of 1: 1, and [Formula E-2] as an electron injection layer, 10 Å, and Al (1000 Å), in this order, to form organic films. A light emitting device was manufactured. 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]

Comparative Examples 1 to 4

The organic light emitting device for the comparative example was fabricated and tested in the same manner except that the following [BH-1] and [BH-2] were used instead of the compound according to the present invention used as a host in the device structure of the above example, The emission characteristics of the organic light emitting device were measured at 0.4 mA. The structures of [BH-1] and [BH-2] are as follows.

[BH-1] [BH-2]

division host EQE T97 Example 1 A-1 9.4 240 Example 2 A-2 9.2 245 Example 3 A-6 9.5 250 Example 4 A-14 9.4 265 Example 5 A-21 9.8 265 Example 6 A-33 10.0 270 Example 7 A-39 9.6 275 Example 8 A-54 10.0 267 Example 9 A-92 9.8 270 Comparative Example 1 BH-1 8.4 180 Comparative Example 2 BH-2 8.9 210

As shown in [Table 1], the organic light emitting compound according to the present invention has both high efficiency and long lifespan characteristics evenly better than Comparative Examples 1 and 2 according to the prior art, so as an organic light emitting device. It shows high applicability.

Claims (20)

An organic light emitting compound represented by the following [Formula A].
[Formula A]

[Structural Formula A]
In the above [Formula A],
R ₁ to R ₁₂ are the same or different, and independently of each other, hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted An alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms Any one selected from;
However, at least one of R ₁ to R ₁₂ is a single bond connected to the linking group L in [Formula A], and binds the chrysene ring in Formula A with Formula A;
In the above [structural formula A],
The linking group L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms;
Wherein n is an integer from 0 to 3, when n is 2 or more, each linking group L is the same as or different from each other,
R ₁₃ to R ₁₈ are the same or different, and independently of each other, hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted An alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms Any one selected from, wherein one of R ₁₃ to R ₁₈ is a single bond connected to the linking group L,
The R ₁₃ to R ₁₈ may be linked to groups adjacent to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,
In [Formula A] and [Structural Formula A], 'substitution' in 'substituted or unsubstituted' 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 group, C1-24 alkenyl group, C1-24 alkynyl group, C3-24 cycloalkyl group, C1-24 heteroalkyl group, C6-24 aryl group, C7-24 aryl Alkyl group, C7-24 alkylaryl group, C2-24 heteroaryl group, C2-24 heteroarylalkyl group, C1-24 alkoxy group, C1-24 alkylamino group, C12-24 carbon atom group Diarylamino group, C2-24 diheteroarylamino group, C7-24 aryl (heteroaryl) amino group, C1-24 alkylsilyl group, C6-24 arylsilyl group, C6-24 aryl It means that it is substituted with one or more substituents selected from the group consisting of an oxy group and an arylthionyl group having 6 to 24 carbon atoms.
According to claim 1,
An organic light-emitting compound, characterized in that at least one of the substituents R _{2 ,} R ₆ , R ₈ and R ₁₂ in the chrysene ring of Formula A is a single bond bonded to the linking group L in Formula A.
According to claim 2,
The substituent R ₆ or R ₈ in the chrysene ring of Formula A is a single bond bonded to the linking group L in the structural formula A, or R ₆ and R ₈ are simultaneously single bonds bonded to the linking group L in the structural formula A. organic light emitting compound
According to claim 1,
The substituent R ₆ in the chrysene ring of Formula A is a single bond bonded to the linking group L in Formula A,
Substituents R _{2 ,} R ₈ and R ₁₂ are each the same as or different from each other and independently of each other hydrogen, heavy hydrogen, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms An organic light emitting compound, characterized in that any one selected from.
According to claim 4,
The substituent R ₆ is a single bond bonded to the linking group L in structural formula A,
The organic light emitting compound, wherein the substituent R ₁₂ is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
According to claim 4,
An organic light emitting compound, characterized in that at least one of the substituents R _{2 ,} R ₈ and R ₁₂ in the chrysene ring of Formula A is any one selected from [Structure Formula 1] to [Structural Formula 5] below.
[Formula 1] [Formula 2] [Formula 3]

[Structural Formula 4] [Structural Formula 5]

In Structural Formulas 1 to 5, the carbon site of the aromatic ring is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 14 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and a substituted or unsubstituted carbon atom having 2 to 20 carbon atoms. One or more substituents selected from the group consisting of heteroaryl groups of may be bonded.
According to claim 1,
The organic light-emitting compound, characterized in that the compound represented by the formula A contains at least one deuterium.
According to claim 7,
At least one of R _{2 ,} R ₆ , R ₈ and R ₁₂ is a substituent containing deuterium;
Alternatively, at least one of R ₁₃ to R ₁₈ is deuterium or a substituent containing deuterium; organic light emitting compound characterized in that.
According to claim 4,
The linking group L in Formula A is an organic light emitting compound, characterized in that a single bond.
According to claim 1,
An organic light-emitting compound, characterized in that at least one of R ₁₃ to R ₁₈ not connected to L in [Structural Formula A] is not hydrogen.
According to claim 10,
In [Formula A], at least one of R ₁₃ to R ₁₈ not connected to L is any one selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms and a substituted and unsubstituted heteroaryl group having 2 to 30 carbon atoms An organic light emitting compound, characterized in that one.
According to claim 11,
An organic light emitting compound, characterized in that at least one of R ₁₃ to R ₁₈ not connected to L in [Structural Formula A] is any one selected from the following [Structural Formula 1] to [Structural Formula 6].
[Formula 1] [Formula 2] [Formula 3]

[Formula 4] [Formula 5] [Formula 6]

In Structural Formulas 1 to 6, the carbon site of the aromatic ring is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 14 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and a substituted or unsubstituted carbon atom having 2 to 20 carbon atoms. One or more substituents selected from the group consisting of heteroaryl groups of may be bonded.
According to claim 1,
The organic light emitting compound, characterized in that the linking group L is a single bond or any one selected from the following [Formula 6] to [Formula 10].
[Formula 6] [Formula 7] [Formula 8]

[Structural Formula 9] [Structural Formula 10]

In the linking group L, hydrogen or deuterium may be bonded to the carbon site of the aromatic ring.
According to claim 1,
The organic light emitting compound, characterized in that the compound is any one selected from the group represented by the following [A-1] to [A-115].

[A-1][A-2][A-3]

[A-4][A-5][A-6]

[A-7][A-8][A-9]

[A-10][A-11][A-12]

[A-13][A-14][A-15]

[A-16][A-17][A-18]

[A-19][A-20][A-21]

[A-22][A-23][A-24]

[A-25][A-26][A-27]

[A-28][A-29][A-30]

[A-31][A-32][A-33]

[A-34][A-35][A-36]

[A-37][A-38][A-39]

[A-40][A-41][A-42]

[A-43][A-44][A-45]

[A-46][A-47][A-48]

[A-49][A-50][A-51]

[A-52][A-53][A-54]

[A-55][A-56][A-57]

[A-58][A-59][A-60]

[A-61][A-62][A-63]

[A-64][A-65][A-66]

[A-67][A-68][A-69]

[A-70][A-71][A-72]

[A-73][A-74][A-75]

[A-76][A-77][A-78]

[A-79][A-80][A-81]

[A-82][A-83][A-84]

[A-85][A-86][A-87]

[A-88][A-89][A-90]

[A-91][A-92][A-93]

[A-94][A-95][A-96]

[A-97][A-98][A-99]

[A-100][A-101][A-102]

[A-103][A-104][A-105]

[A-106][A-107][A-108]

[A-109][A-110][A-111]

[A-112][A-113][A-114]

[A-115]
a first electrode;
a second electrode facing the first electrode; and
An organic light emitting device comprising: an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one compound selected from claims 1 to 14.
According to claim 15,
The organic layer comprises 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.
17. The method of claim 16,
An organic light emitting device, characterized in that 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 compound is used as a host.
18. The method of claim 17,
The dopant is an organic light emitting device, characterized in that at least one selected from the following [Formula D1] to [Formula D10] is used.
[Formula D1]

[Formula D2]

In [Formula D1] and [Formula D2], A ₃₁ , A ₃₂ , E ₁ and F ₁ are each the same or different, and independently of each other, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or It is an unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms;
The two carbon atoms adjacent to each other in the aromatic ring of A ₃₁ and the two carbon atoms adjacent to each other in the aromatic ring of A ₃₂ form a 5-membered ring with the carbon atoms connected to the substituents R ₅₁ and R ₅₂ , respectively. form;
The linking groups L ₂₁ to L ₃₂ are each the same or different, and independently of each other, a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted C6 to 60 carbon atoms It is selected from an arylene group or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
W and W' are any one selected from NR ₅₃ , CR ₅₄ R ₅₅ , SiR ₅₆ R ₅₇ , GeR ₅₈ R ₅₉ , O, S, and Se;
The substituents R ₅₁ to R ₅₉ and Ar ₂₁ to Ar ₂₈ are the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms A cycloalkenyl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, substituted or unsubstituted alkylamine having 1 to 30 carbon atoms substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, substituted or unsubstituted carbon atoms Any one selected from an alkyl germanium group having 1 to 30, a substituted or unsubstituted aryl germanium group having 1 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group,
The R ₅₁ and R ₅₂ may be connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring are N, O, P, Si, or S. , Ge, Se, may be substituted with one or more heteroatoms selected from Te;
wherein p11 to p14, r11 to r14 and s11 to s14 are each an integer of 1 to 3, and when each of them is 2 or more, the linking groups L ₂₁ to L ₃₂ are the same as or different from each other;
wherein x1 is 1, y1, z1 and z2 are each the same or different, and are independently integers from 0 to 1;
Ar ₂₁ and Ar ₂₂ , Ar ₂₃ and Ar ₂₄ , Ar ₂₅ and Ar ₂₆ , and Ar ₂₇ and Ar ₂₈ may be connected to each other to form a ring;
Two carbon atoms adjacent to each other in the A ₃₂ ring in Formula D1 combine with * in Structural Formula Q ₁₁ to form a condensed ring,
In Chemical Formula D2, two adjacent carbon atoms in the A ₃₁ ring combine with * in Structural Formula Q ₁₂ to form a condensed ring, and two adjacent carbon atoms in the A ₃₂ ring are combined with * in Structural Formula Q ₁₁ and They can combine to form a condensed ring.

[Formula D3]

In the above [Formula D3],
Wherein X ₁ Is any one selected from B, P, P=O
T1 to T3 are the same as or different from each other, and independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms;
Y1 is any one selected from N-R61, CR62R63, O, S, and SiR64R65;
Y2 is any one selected from N-R66, CR66R68, O, S, and SiR69R70;
R61 to R70 are each the same as or different from each other, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted carbon atom A cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted Unsubstituted C1-C30 alkylthioxy group, substituted or unsubstituted C5-C30 arylthioxy group, substituted or unsubstituted C1-C30 alkylamine group, substituted or unsubstituted C5-C30 Any one selected from an arylamine group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, and a halogen group, wherein R61 to R70 are each An alicyclic or aromatic monocyclic or polycyclic ring may be additionally formed by combining with one or more rings selected from T1 to T3.

[Formula D4] [Formula D5]

In [Formula D4] and [Formula D5],
X ₂ is any one selected from B, P, and P=O;
T ₄ to T ₆ are the same as T ₁ to T ₃ in [Formula D3],
Y4 is any one selected from N-R61, CR62R63, O, S, and SiR64R65;
Y5 is any one selected from N-R66, CR66R68, O, S, SiR69R70
Y6 is any one selected from N-R71, CR72R73, O, S, and SiR74R75;
R61 to R75 are the same as R61 to R70 in [Formula D3].

[Formula D6] [Formula D7]

X ₃ is any one selected from B, P, and P=O;
T ₇ to T ₉ are the same as T ₁ to T ₃ in [Formula D3],
Y ₆ is any one selected from N-R61, CR62R63, O, S, and SiR64R65;
The substituents R ₆₁ to R ₆₅ and R ₇₁ to R ₇₂ are each the same as R61 to R70 in [Formula D3],
R ₇₁ and R ₇₂ are connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, or combined with the T ₇ ring or T ₉ ring to additionally form an alicyclic or aromatic monocyclic or polycyclic ring. can do.

Formula D8] [Formula D9]

[Formula D10]

In [Formula D8] to [Formula D10],
Wherein X is any one selected from B, P, P = O,
The Q1 to Q3 are the same as T ₁ to T ₃ in [Formula D3],
The linking group Y is any one selected from NR ₃ , CR 4 R 5 , O, S, and Se;
The substituents R3 to R5 are the same as R61 to R70 in [Formula D3], respectively,
The R ₃ to R ₅ may each be bonded to the Q ₂ ring or the Q ₃ ring to further form an alicyclic or aromatic monocyclic or polycyclic ring,
The R ₄ and R ₅ may be linked to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,
The ring formed by the Cy1 has a nitrogen (N) atom, an aromatic carbon atom in the Q1 ring to which the nitrogen (N) atom is bonded, and an aromatic carbon atom in the Q1 ring to be bonded to the Cy1, substituted or unsubstituted carbon atoms 1 to 10 alkylene groups,
In Formula D9,
'Cy2' may be added to Cy1 to form a saturated hydrocarbon ring, and the ring formed by Cy2 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, except for carbon atoms included in Cy1,
In the above formula D10,
The ring formed by the Cy3 is an aromatic carbon atom in the Q3 ring to be bonded to Cy3, an aromatic carbon atom in Q3 to be bonded to a nitrogen (N) atom, a nitrogen (N) atom, and in Cy1 to which the nitrogen (N) atom is bonded. Excluding carbon atoms, it is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,
Here, 'substitution' in the 'substituted or unsubstituted' in [Formula D1] to [Formula D10] is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a carbon number 1 -24 halogenated alkyl group, C2-24 alkenyl group, C2-24 alkynyl group, C3-24 cycloalkyl group, C1-24 heteroalkyl group, C6-24 aryl group, C7-24 Arylalkyl group having 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, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, and 12 carbon atoms to 24 diarylamino group, C2 to 24 diheteroarylamino group, C7 to 24 aryl (heteroaryl) amino group, C1 to 24 alkylsilyl group, C6 to 24 arylsilyl group, C6 to 24 It means that it is substituted with one or more substituents selected from the group consisting of an aryloxy group of 24 and an arylthionyl group of 6 to 24 carbon atoms.
According to claim 16,
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 15,
The organic light emitting diode may include a flat panel display device; flexible display devices; devices for monochromatic or white flat lighting; devices for flexible lighting in monochromatic or white; vehicle display devices; And a display device for virtual or augmented reality; organic light emitting device characterized in that used in any one device selected from.

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