KR102439581B1 - Organic light emitting diode including Novel Organic compounds in light emitting layer - Google Patents

Abstract

The present invention relates to an organic light emitting device comprising an organic compound represented by [Formula A] or [Formula B], and more particularly, to an organic light emitting device comprising two light emitting layers between a first electrode and a second electrode, It relates to an organic light emitting device using an organic compound represented by the [Formula A] or [Formula B] in at least one of the light emitting layers, wherein the [Formula A] and [Formula B] are the same as described in the detailed description of the invention do.

Description

Organic light emitting diode including Novel Organic compounds in light emitting layer

The present invention relates to an organic light emitting device comprising a novel compound that can be used in an organic light emitting device in a light emitting layer, and more particularly, to an organic light emitting device comprising two light emitting layers between a first electrode and a second electrode, and among the two light emitting layers By introducing the novel organic compound into at least one, it relates to an organic light emitting device capable of realizing device characteristics of high luminous efficiency, low voltage driving, and long life.

An organic light emitting diode (OLED) is a display using a self-emission phenomenon, has a large viewing angle, can be lightweight and compact compared to a liquid crystal display, and has advantages such as a fast response speed and thus a full-color (full-color) display. ) is expected to be applied to displays or lighting.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered 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, an electron injection layer, and the like. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons It lights up when it falls back to the ground state. 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.

A material used as an organic layer in an organic light emitting device may be classified into a light emitting material and a charge transport material, for example, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like, according to functions. The light emitting material can be classified into a high molecular type and a low molecular type according to the molecular weight, and can be classified into a fluorescent material derived from a singlet excited state of an electron and a phosphorescent material derived from a triplet excited state of an electron according to the light emission mechanism. .

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength moves to a longer wavelength due to intermolecular interaction, and there is a problem in that the color purity is lowered or the efficiency of the device is decreased due to the emission attenuation effect, so that the increase in color purity and energy A host-dopant system can be used as a luminescent material to increase the luminous efficiency through transition.

The principle is that when a small amount of a dopant having a smaller energy band gap than that of the host forming the emission layer is mixed in the emission layer, excitons generated in the emission 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 band of the dopant, light having a desired wavelength can be obtained according to the type of the dopant used.

Among these light emitting layers, a heterocyclic compound has been recently studied as a host compound, and as a related prior art, Korean Patent Publication No. 10-2016-0089693 (2016.07.28) discloses a structure in which a dibenzofuran ring is bonded to an anthracene ring. It is described with respect to a compound and an organic light emitting device including the same, and in addition, in Patent Publication No. 10-2017-0055743 (2017.05.22), aryl on 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, although various types of compounds for use in the light emitting layer of the organic light emitting device have been prepared including the prior art, it is still applicable for the organic light emitting device, and has high efficiency, low voltage driving and long life. The need for the development of an organic light emitting device is continuously demanded.

Laid-Open Patent Publication No. 10-2016-0089693 (2016.07.28) Laid-open Patent Publication No. 10-2017-0055743 (2017.05.22)

Therefore, the first technical task to be achieved by the present invention is to use a novel organic compound that can be used as a host material for the light emitting layer in the organic light emitting device, to provide a high efficiency, low voltage driving and long life organic light emitting diode (OLED) will provide

The present invention in order to achieve the above technical problems, a first electrode; and a second electrode opposite to the first electrode. a first light emitting layer comprising a first host and a first dopant between the first electrode and the second electrode; and a second light emitting layer comprising a second host and a second dopant; sequentially, wherein at least one of the first host and the second host is a compound represented by the following [Formula A] or [Formula B] 1 It provides an organic light emitting device, characterized in that it comprises more than one species.

[Formula A] [Formula B]

In the [Formula A] and [Formula B],

Wherein R ₁ to R ₁₄ are the same or different, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted A cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted 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, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, a halogen group any one selected from;

The linking groups L ₁ and L ₂ are the same or different from each other, and are each independently 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, and ;

Wherein n1 and n2 are each the same or different, and each independently an integer of 0 to 2, when each of them is 2, each linking group L ₁ and L ₂ are the same or different from each other,

Wherein R and R' are the same or different, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C 3 to 30 cycloalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C2 to C50 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine group, substituted or an unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, or a halogen group. any one selected;

Wherein n3 and n4 are each the same or different, and independently of each other are integers of 1 to 9, but when each of them is 2 or more, each R and R' are the same or different from each other, and

In the above [Formula A] and [Formula B], 'substitution' in 'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, and 1 to 24 carbon atoms. Halogenated alkyl group, C1-C24 alkenyl group, C1-C24 alkynyl group, C3-C24 cycloalkyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C7-C24 aryl group Alkyl group, C7-C24 alkylaryl group, C2-C24 heteroaryl group, C2-C24 heteroarylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C12-C24 heteroaryl group Diarylamino group, diheteroarylamino group having 2 to 24 carbon atoms, aryl (heteroaryl)amino group having 7 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, arylsilyl group having 6 to 24 carbon atoms, aryl having 6 to 24 carbon atoms It means being 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.

In the case of the organic light emitting device having two light emitting layers in the organic light emitting device according to the present invention and introducing the organic compound represented by Formula A or Formula B into at least one of them, compared to the organic light emitting device according to the prior art It is possible to provide an organic light emitting device exhibiting more high efficiency, low voltage driving, and long lifespan.

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

Hereinafter, the present invention will be described in more detail. In each drawing of the present invention, the size or dimension of the structures is enlarged or reduced than the actual size for clarity of the present invention, and the known components are omitted to reveal the characteristic configuration, so it is not limited to the drawings. .

In addition, since the size and thickness of each component shown in the drawings are arbitrarily indicated for convenience of description, the present invention is not necessarily limited to the illustrated bar, and the thickness is enlarged to clearly express various layers and regions in the drawings. indicated. And in the drawings, for convenience of explanation, the thickness of some layers and regions is exaggerated. When a part, such as a layer, film, region, plate, etc., is "on" another part, it includes not only the case where it is "on" another part, but also the case where there is another part in between.

In addition, throughout the specification, when a part "includes" a certain component, this means that other components may be further included rather than excluding other components unless otherwise stated. In addition, throughout the specification, "on" means to be located above or below the target part, and does not necessarily mean to be located above the gravitational direction.

The present invention is a first electrode; and a second electrode opposite to the first electrode. a first light emitting layer comprising a first host and a first dopant between the first electrode and the second electrode; and a second light emitting layer comprising a second host and a second dopant; sequentially, wherein at least one of the first host and the second host is a compound represented by the following [Formula A] or [Formula B] 1 It provides an organic light emitting device, characterized in that it comprises more than one species.

[Formula A] [Formula B]

In the [Formula A] and [Formula B],

Wherein R ₁ to R ₁₄ are the same or different, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted A cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted 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, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, a halogen group any one selected from;

The linking groups L ₁ and L ₂ are the same or different from each other, and are each independently 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, and ;

Wherein n1 and n2 are each the same or different, and each independently an integer of 0 to 2, when each of them is 2, each linking group L ₁ and L ₂ are the same or different from each other,

Wherein R and R' are the same or different, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C 3 to 30 cycloalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C2 to C50 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine group, substituted or an unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, or a halogen group. any one selected;

Wherein n3 and n4 are each the same or different, and independently of each other are integers of 1 to 9, but when each of them is 2 or more, each R and R' are the same or different from each other, and

In [Formula A] and [Formula B], 'substitution' in 'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, and 1 to 24 carbon atoms. Halogenated alkyl group, C1-C24 alkenyl group, C1-C24 alkynyl group, C3-C24 cycloalkyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C7-C24 aryl group Alkyl group, C7-C24 alkylaryl group, C2-C24 heteroaryl group, C2-C24 heteroarylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C12-C24 Diarylamino group, diheteroarylamino group having 2 to 24 carbon atoms, aryl (heteroaryl)amino group having 7 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, arylsilyl group having 6 to 24 carbon atoms, aryl having 6 to 24 carbon atoms It means being 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 group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms", "substituted or unsubstituted aryl group having 5 to 50 carbon atoms" in the present invention, The range of carbon number of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms means the total number of carbon atoms constituting the alkyl portion or the aryl portion when viewed as unsubstituted without considering the portion substituted by the substituent. will be. For example, a phenyl group substituted with a butyl group 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.

The aryl group, which is a substituent used in the compound of the present invention, is an organic radical derived from an aromatic hydrocarbon by removal of one hydrogen. When the aryl group has a substituent, it is fused with neighboring substituents to form an additional ring. 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, and aromatic groups such as a pyrenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a peryleneyl group, a chrysenyl group, a naphthacenyl group, a fluoranthenyl group, and the like, wherein at least one hydrogen atom of the aryl group is deuterium An atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH(R), -N(R')(R''), R' and R" are independently of each other the number of carbon atoms an alkyl group of 1 to 10, in this case referred to as an "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 a heteroarylalkyl group of 2 to 24.

The heteroaryl group as a substituent used in the compound of the present invention includes 1, 2, or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te, and the remaining ring atoms are carbon atoms having 2 to 24 carbon atoms. of a ring aromatic system, wherein the rings may be fused to form a ring. And one or more hydrogen atoms in the heteroaryl group may be substituted with the same substituents as in the case 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 heterocyclic ring preferably has 1 to 3 aromatic carbons in the aromatic hydrocarbon including N, O, P, It may be substituted with one or more heteroatoms selected from Si, S, Ge, Se, and Te.

The 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 substituent as in the case of the aryl group.

'cyclo' in the cycloalkyl group as 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, for example, specific examples of the cycloalkyl group include cyclopropyl, cyclo butyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decahydronaphthyl, norbornyl, bornyl, isobornyl, etc. and 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 a cycloalkyl group, and specific examples thereof include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso -amyloxy, hexyloxy, cyclobutyloxy, cyclopentyloxy, adamantanoxy, dicyclopentanoxy, bornyloxy, isobornyloxy, etc., wherein at least one hydrogen atom of 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 as a substituent used in the compound of the present invention include phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl naphthylethyl, and the like, and at least one hydrogen atom of the arylalkyl group is the aryl It can be substituted with the same substituent as in the case of the group.

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

In addition, in the present invention, an alkenyl group means an alkyl substituent including one carbon-carbon double bond formed by two carbon atoms, and an alkynyl group is one 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 induced by the removal of two hydrogens in an alkane molecule, which is a linear or branched saturated hydrocarbon, and a specific example of the alkylene group is a methylene group. , an ethylene group, a propylene group, an isopropylene group, an isobutylene group, a sec-butylene group, a tert-butylene group, a pentylene group, an iso-amylene group, a hexylene group, and the like, and at least one hydrogen of the alkylene group Atoms can be substituted with the same substituents as in the case of the above aryl group.

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

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

In the present invention, the organic compound represented by [Formula A] and [Formula B] is a compound used as a host in the light emitting layer, and the organic compound represented by [Formula A] is a specific compound in a substituted or unsubstituted pyrene ring. It is technically characterized in that the linking group L1 is bonded to the position (see Structural Formula C below) and the 1st position of the substituted or unsubstituted dibenzofuran group is bonded to the linking group L1, and the organic compound represented by the above [Formula B] The technical feature is that the linking group L2 is bonded to a specific position (see Structural Formula C below) in the substituted or unsubstituted pyrene ring, and the 2-position of the substituted or unsubstituted dibenzofuran group is bonded to the linking group L2.

[Structural Formula C]

In the [Formula A] and [Formula B] in the organic light emitting device according to the present invention, the compound represented by Formula A may include at least one deuterium, and the compound represented by Formula B is at least one deuterium may include.

More specifically, at least one of R ₁ to R ₇ in [Formula A] is a substituent containing deuterium, and at least one of R ₈ to R ₁₄ in [Formula B] is a substituent containing deuterium can

In addition, in the organic light emitting device according to the present invention, the compound represented by Formula A may include at least one or more deuterium, and the compound represented by Formula B may include at least one or more deuterium. At least one R in Formula A] may be a substituent containing deuterium, and at least one R' in [Formula B] may be a substituent containing deuterium.

In addition, in one embodiment according to the present invention, R ₁ to R _14, R, R' are the same or different and each independently represent hydrogen, deuterium, a substituted or unsubstituted C 1 to C 10 alkyl group, substituted or unsubstituted A substituted or unsubstituted C 6 to C 18 aryl group, a substituted or unsubstituted C 2 to C 18 heteroaryl group, a substituted or unsubstituted C 3 to C 18 cycloalkyl group, or a substituted or unsubstituted C 1 to C 15 alkylsilyl group , may be a substituent selected from a substituted or unsubstituted C6-C20 arylsilyl group, a cyano group, and a halogen group.

In addition, as an embodiment according to the present invention, at least one of R ₁ to R ₇ in [Formula A] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and R ₈ to in [Formula B] At least one of R ₁₄ may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

In addition, as an embodiment according to the present invention, the linking groups L ₁ and L ₂ in Formulas A and B may each be a single bond, or any one selected from the following [Structural Formula 1] to [Structural Formula 5].

[Structural formula 1] [Structural formula 2] [Structural formula 3]

[Structural formula 4] [Structural formula 5]

Hydrogen or deuterium may be bonded to the carbon site of the aromatic ring in [Structural Formula 1] to [Structural Formula 5].

In addition, according to an embodiment of the present invention, the linking groups L ₁ and L ₂ may each be a single bond.

Also, according to an embodiment of the present invention, n3 and n4 in Formulas A and B may be 1, respectively.

In addition, as an embodiment according to the present invention, at least one R in [Formula A] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and at least one R' in [Formula B] is substituted Or it may be an unsubstituted aryl group having 6 to 18 carbon atoms, and in this case, preferably, n3 and n4 in Formulas A and B are each 1, and R in [Formula A] is substituted or unsubstituted It is a cyclic aryl group having 6 to 18 carbon atoms, and R' in [Formula B] may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

In addition, as an embodiment according to the present invention, the organic compound represented by the [Formula A] or [Formula B] is It may be a compound represented by any one of the following [Formula A-1] or [Formula B-1].

[Formula A-1] [Formula B-1]

In this case, in the [Formula A-1] and [Formula B-1], the substituents R ₁ to R _{14, the} linking groups L ₁ and L ₂ , n1 and n2 are as previously defined in [Formula A] or [Formula B] same,

The substituents R and R' are substituted or unsubstituted aryl groups having 6 to 18 carbon atoms.

In addition, in one embodiment according to the present invention, n3 and n4 in Formulas A and B are each 1, and at least one of R ₁ to R _{7 and} R in [Formula A] is deuterium substituted carbon number of 6 to 18 aryl group, and at least one of R ₈ to R _{14 and} R' in [Formula B] may be an aryl group having 6 to 18 carbon atoms substituted with deuterium.

In addition, as an embodiment of the present invention, n3 and n4 in Formulas A and B are each 1, and R in [Formula A] is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms. , R' in [Formula B] may be a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.

In addition, the compound represented by [Formula A] or [Formula B] according to the present invention may be any one compound selected from [Formula 1] to [Formula 240].

Formula 1 Formula 2 Formula 3

Formula 4 Formula 5 Formula 6

Formula 7 Formula 8 Formula 9

Formula 10 Formula 11 Formula 12

Formula 13 Formula 14 Formula 15

Formula 16 Formula 17 Formula 18

Formula 19 Formula 20 Formula 21

Formula 22 Formula 23 Formula 24

Formula 25 Formula 26 Formula 27

Formula 28 Formula 29 Formula 30

Formula 31 Formula 32 Formula 33

Formula 34 Formula 35 Formula 36

Formula 37 Formula 38 Formula 39

Formula 40 Formula 41 Formula 42

Formula 43 Formula 44 Formula 45

Formula 46 Formula 47 Formula 48

Formula 49 Formula 50 Formula 51

Formula 52 Formula 53 Formula 54

Formula 55 Formula 56 Formula 57

Formula 58 Formula 59 Formula 60

Formula 61 Formula 62 Formula 63

Formula 64 Formula 65 Formula 66

Formula 67 Formula 68 Formula 69

Formula 70 Formula 71 Formula 72

Formula 73 Formula 74 Formula 75

Formula 76 Formula 77 Formula 78

Formula 79 Formula 80 Formula 81

Formula 82 Formula 83 Formula 84

Formula 85 Formula 86 Formula 87

Formula 88 Formula 89 Formula 90

Formula 91 Formula 92 Formula 93 Formula

Formula 94 Formula 95 Formula 96

Formula 97 Formula 98 Formula 99

Formula 100 Formula 101 Formula 102

Formula 103 Formula 104 Formula 105

Formula 106 Formula 107 Formula 108

Formula 109 Formula 110 Formula 111

Chemical formula 112 Chemical formula 113 Chemical formula 114

Formula 115 Formula 116 Formula 117 Formula

Formula 118 Formula 119 Formula 120

Chemical formula 121 Chemical formula 122 Chemical formula 123

Formula 124 Formula 125 Formula 126

Formula 127 Formula 128 Formula 129

Formula 130 Formula 131 Formula 132

Formula 133 Formula 134 Formula 135

Formula 136 Formula 137 Formula 138

Formula 139 Formula 140 Formula 141

Formula 142 Formula 143 Formula 144

Formula 145 Formula 146 Formula 147 Formula

Formula 148 Formula 149 Formula 150

Formula 151 Formula 152 Formula 153

Formula 154 Formula 155 Formula 156

Formula 157 Formula 158 Formula 159

Formula 160 Formula 161 Formula 162

Formula 163 Formula 164 Formula 165

Formula 166 Formula 167 Formula 168

Formula 169 Formula 170 Formula 171

Formula 172 Formula 173 Formula 174

Formula 175 Formula 176 Formula 177

Formula 178 Formula 179 Formula 180

Formula 181 Formula 182 Formula 183

Formula 184 Formula 185 Formula 186

Formula 187 Formula 188 Formula 189

Formula 190 Formula 191 Formula 192

Formula 193 Formula 194 Formula 195 Formula

Formula 196 Formula 197 Formula 198

Formula 199 Formula 200 Formula 201

Formula 202 Formula 203 Formula 204

Formula 205 Formula 206 Formula 207

Formula 208 Formula 209 Formula 210

Formula 211 Formula 212 Formula 213

Formula 214 Formula 215 Formula 216

Formula 217 Formula 218 Formula 219

Formula 220 Formula 221 Formula 222

Formula 223 Formula 224 Formula 225

Formula 226 Formula 227 Formula 228

Formula 229 Formula 230 Formula 231

Formula 232 Formula 233 Formula 234

Formula 235 Formula 236 Formula 237

Formula 238 Formula 239 Formula 240

Meanwhile, in the present invention, "(organic layer) includes one or more organic compounds" means "one organic compound belonging to the scope of the present invention or two or more different types belonging to the scope of the organic compound. may include 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 a hole injection function and a hole transport function at the same time, a light emitting layer, an electron transport layer, and an electron injection layer.

In the present invention, at least one of a hole transport layer and a hole injection layer is provided between the first electrode and the first light emitting layer, and at least one of an electron transport layer and an electron injection layer is provided between the second light emitting layer and the second electrode Preferably, an organic light emitting device in which a hole transport layer and a hole injection layer are respectively provided between the first electrode and the first light emitting layer, and an electron transport layer and an electron injection layer are respectively provided between the second light emitting layer and the second electrode can provide

In addition, in the organic light-emitting device according to the present invention, at least one of the first dopant in the first light-emitting layer or the second dopant in the second light-emitting layer is at least one compound represented by any one of the following [Formula D1] to [Formula D10] may include, and preferably, both the first dopant in the first light-emitting layer and the second dopant in the second light-emitting layer are the same or different, and any one selected from the above [Formula D1] to [Formula D10] The above compounds can be used.

[Formula D1]

[Formula D2]

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

Two carbon atoms adjacent to each other in the aromatic ring of A ₃₁ and 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. to form;

The linking groups L ₂₁ to L ₃₂ are the same or different, and are each independently a single bond, a substituted or unsubstituted C 1 to C 60 alkylene group, a substituted or unsubstituted C 2 to C 60 alkenylene group, 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-C60 cycloalkylene group It is selected from an arylene group or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;

W and W' are the same or different from each other and are each independently 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 , Ar ₂₁ to Ar ₂₈ are the same or different, and are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, or a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted C5 to 30 of a cycloalkenyl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C1-C30 alkylthioxy group, substituted or unsubstituted C5-C30 arylthioxy group, substituted or unsubstituted C1-C30 alkylamine group, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, 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 substituted or unsubstituted carbon number Any one selected from a 1 to 30 alkyl germanium group, a substituted or unsubstituted C 1 to C 30 aryl germanium group, a cyano group, a nitro group, and a halogen group,

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, S , Ge, Se, may be substituted with any 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 these is 2 or more, each of the connecting groups L ₂₁ to L ₃₂ is the same as or different from each other,

Wherein x1 is 1, y1, z1 and z2 are each the same or different, and are each independently an integer of 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;

In Formula D1, two carbon atoms adjacent to each other in ring A ₃₂ are combined with * in Formula Q ₁₁ to form a condensed ring,

In Formula D2, two adjacent carbon atoms in the A ₃₁ ring combine with * of the structural formula Q ₁₂ to form a condensed ring, and two adjacent carbon atoms in the A ₃₂ ring combine with the * in the structural formula Q ₁₁ Combined to form a condensed ring.

[Formula D3]

In the [Formula D3],

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

wherein T1 to T3 are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocycle 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;

wherein R61 to R70 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted carbon number A 3 to 30 cycloalkyl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or An unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C5-C30 arylthioxy group, a substituted or unsubstituted C1-C30 alkylamine group, a 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 It may be combined with one or more rings selected from T1 to T3 to additionally form an alicyclic or aromatic monocyclic or polycyclic ring.

[Formula D4] [Formula D5]

In the [Formula D4] and [Formula D5],

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

The 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]

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

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

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

[Formula D8] [Formula D9]

[Formula D10]

In the [Formula D8] to [Formula D10],

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

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

The linking group Y is any one selected from NR ₃ , CR4R5, O, S, and Se,

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

The R ₃ to R ₅ may be combined with each of the Q ₂ ring or the Q ₃ ring to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,

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

The ring formed by 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 Cy1, substituted or unsubstituted carbon number 1 to 10 alkylene groups,

In the formula D9,

The '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 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, in Cy1 to which the nitrogen (N) atom is bonded Except for carbon atoms, it is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,

Here, the 'substitution' in the 'substituted or unsubstituted' in the [Formula D1] to [Formula D10] is deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, 1 carbon number to 24 halogenated alkyl group, C2-C24 alkenyl group, C2-C24 alkynyl group, C3-C24 cycloalkyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C7-C7 24 arylalkyl group, C7-C24 alkylaryl group, C2-C24 heteroaryl group, C2-C24 heteroarylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C12 A diarylamino group having to 24, a diheteroarylamino group having 2 to 24 carbon atoms, an aryl (heteroaryl)amino group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms It means to be substituted with one or more substituents selected from the group consisting of an aryloxy group having 6 to 24 carbon atoms and an arylthionyl group having 6 to 24 carbon atoms. A 1 to 12 alkyl group, a halogenated alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a heteroalkyl group having 1 to 12 carbon atoms, 6 to carbon atoms 18 aryl group, C7 to C20 arylalkyl group, C7 to C20 alkylaryl group, C2 to C18 heteroaryl group, C2 to C18 heteroarylalkyl group, C1 to C12 alkoxy group, C1 to 12 alkylamino group, C12 to C18 diarylamino group, C2 to C18 diheteroarylamino group, C7 to C18 aryl (heteroaryl)amino group, C1 to C12 alkylsilyl group, C6 to C18 of an arylsilyl group, an aryloxy group having 6 to 18 carbon atoms, and 6 carbon atoms. to 18 may be substituted with one or more substituents selected from the group consisting of arylthionyl groups.

In addition, in the case of the boron compound represented by any one of the [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 heterocycle is substituted As possible substituents, deuterium, 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, or an arylamino group having 6 to 24 carbon atoms may be substituted, wherein the C1-C24 arylamino group may be substituted. Each alkyl group or aryl group in the alkylamino group and the arylamino group having 6 to 24 carbon atoms may be connected to each other, and more preferred substituents include an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, and an alkylamino group having 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 connected to each other.

On the other hand, as a specific example of the compound represented by any one of the [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, the compound represented by any one of the following d 1 to d 239 can be

<d 1 > <d 2 > <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 > <d 71 > <d 72>

<d 73 > <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>

<d 235 > <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>

In addition, 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 one selected.

[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] [D 235] [D 236]

[D 237] [D 238] [D 239] [D 240]

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

[D 245] [D 246] [D 247] [D 248]

[D 249] [D 250] [D 251] [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] [D 300]

[D 301] [D 302] [D 303] [D 304]

[D 305] [D 306] [D 307] [D 308]

[D 309] [D 310] [D 311] [D 312]

[D 313] [D 314] [D 315] [D 316]

[D 317] [D 318] [D 319] [D 320]

[D 321] [D 322] [D 323] [D 324]

[D 325] [D 326] [D 327] [D 328]

[D 329] [D 330] [D 331] [D 332]

[D 333] [D 334] [D 335] [D 336]

[D 337] [D 338] [D 339] [D 340]

[D 341] [D 342] [D 343] [D 344]

[D 345] [D 346] [D 347]

[D 348] [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]

[D 414] [D 415] [D 416]

[D 417] [D 418] [D 419]

[D 420] [D 421] [D 422]

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

[D 426] [D 427] [D 428]

[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]

[D 444] [D 445] [D 446]

[D 447] [D 448] [D 449]

[D 450] [D 451] [D 452]

[D 453] [D 454] [D 455]

[D 456] [D 457] [D 458]

[D 459] [D 460] [D 461]

[D 462] [D 463] [D 464]

[D 465] [D 466] [D 467]

[D 468] [D 469] [D 470]

[D 471] [D 472] [D 473]

[D 474] [D 475] [D 476]

In addition, 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 <D 501> to <D 587>. .

<D 501> <D 502> <D 503>

<D 504> <D 505> <D 506>

<D 507> <D 508> <D 509>

<D 510> <D 511> <D 512>

<D 513> <D 514> <D 515>

<D 516> <D 517> <D 518>

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

<D 522> <D 523> <D 524>

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

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

<D 531> <D 532> <D 533>

<D 534> <D 535> <D 536>

<D 537> <D 538> <D 539>

<D 540> <D 541> <D 542>

<D 543> <D 544> <D 545>

<D 546> <D 547> <D 548>

<D 549> <D 550> <D 551>

<D 552> <D 553> <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 generally selected from about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

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

In addition, as a preferred embodiment of the organic light emitting device according to the present invention, the first light emitting layer may include at least one compound selected from among the compounds represented by the [Formula A] or [Formula B]. have.

Here, when the first light emitting layer in the organic light emitting device according to the present invention contains any one compound selected from compounds represented by [Formula A] or [Formula B], the second light emitting layer has the following [Formula E] An anthracene derivative represented by can be used as a host.

[Formula E]

In the above [Formula E],

The substituents R ₄₁ to R ₅₆ are the same or different, and are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted A cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, Any one selected from a cyano group, a nitro group, a halogen group,

The substituent Ar ₅ is a substituted or unsubstituted C 6 to C 50 aryl group, or a substituted or unsubstituted C 2 to C 50 heteroaryl group,

The linking group L ₁ is any one 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 of 1 to 2, and when n is 2 or more, each linking group L1 is the same as or different from each other,

'Substitution' in the 'substituted or unsubstituted' in [Formula E] is deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, C2-C24 alkenyl group, C2-C24 alkynyl group, C3-C24 cycloalkyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C7-C24 arylalkyl group, C7 to 24 alkylaryl group, C2-C24 heteroaryl group, C2-C24 heteroarylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C12-C24 diarylamino group, A diheteroarylamino group having 2 to 24 carbon atoms, an aryl (heteroaryl)amino group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, an aryloxy group having 6 to 24 carbon atoms. It means being substituted with one or more substituents selected from the group consisting of 6 to 24 arylthionyl groups.

In addition, the anthracene derivative represented by Formula E in the second light emitting layer in the present invention may contain at least one deuterium. In this case, at least one of the substituents R ₄₁ to R ₅₆ , or Ar5 may be a deuterium-substituted aryl group having 6 to 18 carbon atoms.

In addition, as a preferred embodiment of the organic light emitting device according to the present invention, when the second light emitting layer includes the anthracene derivative represented by the [Formula E] as a host, the anthracene derivative represented by the [Formula E] is more As a preferred structure, an anthracene derivative represented by the following [Formula E-1] or [Formula E-2] may be used.

[Formula E-1]

[Formula E-2]

In the [Formula E-1] and [Formula E-2],

The substituents R ₄₁ to R _{48 and} R ₄₉ to R ₅₅ are the same or different, and each independently represent hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, or a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to any one selected from an arylsilyl group, a cyano group, a nitro group, and a halogen group of 30;

The substituent Ar ₅ is a substituted or unsubstituted C 6 to C 50 aryl group, or a substituted or unsubstituted C 2 to C 50 heteroaryl group,

The linking group L ₁₁ is any one 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 k is an integer of 1 to 2, when k is 2 or more, each connecting group L ₁₁ is the same as or different from each other,

'Substitution' in the 'substituted or unsubstituted' in [Formula E-1] and [Formula E-2] is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro 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 cycloalkyl group having 3 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms. An arylalkyl group having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, A diarylamino group having 12 to 24 carbon atoms, a diheteroarylamino group having 2 to 24 carbon atoms, an aryl (heteroaryl)amino group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, and an arylsilyl group having 6 to 24 carbon atoms. It means being substituted with one or more substituents selected from the group consisting of an aryloxy group having 6 to 24 and an arylthionyl group having 6 to 24 carbon atoms.

In addition, as a more preferred example of 'substitution' in 'substituted or unsubstituted' in [Formula E], [Formula E-1] and [Formula E-2], it is a deuterium, a cyano group, a halogen group , hydroxy group, nitro group, alkyl group having 1 to 12 carbon atoms, halogenated alkyl group having 1 to 12 carbon atoms, alkenyl group having 2 to 12 carbon atoms, alkynyl group having 2 to 12 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, cycloalkyl group having 1 to 12 carbon atoms of a heteroalkyl group, an aryl group having 6 to 18 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, a heteroaryl group having 2 to 18 carbon atoms, a heteroarylalkyl group having 2 to 18 carbon atoms, 1 to carbon atoms 12 alkoxy group, C 1 to C 12 alkylamino group, C 12 to C 18 diarylamino group, C 2 to C 18 diheteroarylamino group, C 7 to C 18 aryl (heteroaryl) amino group, C 1 to C 12 alkyl It may be substituted with one or more substituents selected from the group consisting of a silyl group, an arylsilyl group having 6 to 18 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, and an arylthionyl group having 6 to 18 carbon atoms.

Here, the compound represented by [Formula E-1] or [Formula E-2] is the 1st or 2nd position of either phenyl ring of dibenzofuran or the other side of dibenzofuran, as shown in Figure 1 below. It is characterized in that the 1' or 2' position of the phenyl ring is bonded to the 9th position of the anthracenyl group or the linking group L ₁₁ .

[그림 1]

[Figure 1]

Meanwhile, in the present invention, the substituent Ar ₅ in the anthracene derivative represented by any one of [Formula E], [Formula E-1] and [Formula E-2] may be a substituent represented by [Structural Formula C-1] below. have.

[Structural formula C-1]

In this case, R ₆₁ to R ₆₅ in the [Structural Formula C-1] are the same or different, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 50 of an aryl group, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number Any one selected from an arylsilyl group of 6 to 30, a halogen group,

'-*' in [Formula C-1] is a binding site bonded to the 10th position of the anthracenyl group in [Formula E], [Formula E-1] or [Formula E-2].

As an embodiment, as a preferred example of the organic light emitting device according to the present invention, the linking group L ₁₁ in the [Formula E-1] or [Formula E-2] is a single bond, or a substituted or unsubstituted C 6 to 14 may be an arylene group of, in this case, k is an integer of 1 to 2, but when k is 2 or more, each L ₁₃ is the same as or different from each other.

In addition, as an embodiment of the present invention, in Formula E, Ar5 may be a substituent containing at least one deuterium, preferably an aryl group having 6 to 50 carbon atoms containing at least one deuterium, more preferably Preferably, an aryl group having 6 to 40 carbon atoms including deuterium, more preferably an aryl group having 6 to 30 carbon atoms including deuterium, more preferably an aryl group having 6 to 24 carbon atoms including deuterium, more preferably It may be an aryl group having 6 to 18 carbon atoms including deuterium, and more preferably a phenyl group substituted with deuterium.

In addition, as an embodiment according to the present invention, at least one of R ₄₁ to R ₄₈ in Formula E may be deuterium, preferably at least 2 or more, more preferably at least 4 or more, and more preferably may be all eight deuterium.

In addition, as an embodiment of the present invention, at least one of R ₄₉ to R ₅₆ in Formula E may be a substituent containing deuterium, preferably an aryl group having 6 to 50 carbon atoms including deuterium, and more Preferably, an aryl group having 6 to 40 carbon atoms including deuterium, more preferably an aryl group having 6 to 30 carbon atoms including deuterium, more preferably an aryl group having 6 to 24 carbon atoms including deuterium, more preferably may be an aryl group having 6 to 18 carbon atoms including deuterium, and more preferably, one or two of R49 to R56 in Formula E may be an aryl group having 6 to 18 carbon atoms substituted with deuterium.

In addition, as an embodiment according to the present invention, the anthracene derivative represented by Formula E may have a deuterated degree of 20% or more, Preferably it may be 30% or more, more preferably it may be 35% or more, more preferably it may be 40% or more, more preferably 45% or more, and more preferably 50% or more.

On the other hand, when looking in detail with respect to the degree of deuteration used in the present specification, in general, the "deuterated derivative" of compound X has the same structure as compound X, but a hydrogen atom bonded to a carbon atom, a nitrogen atom or an oxygen atom in the compound X. with at least one deuterium (D) replacing (H).

In this case, the term "yy % deuterated" or "yy % deuterated" refers to the ratio of deuterium to the sum of all hydrogens and deuterium directly bonded to a carbon atom, nitrogen atom, or oxygen atom in compound X. refers to

Therefore, if two out of six hydrogens in benzene are deuterated, the degree of deuteration in the compound C6H4D2 can be regarded as 2/(4+2) X 100 = 33% deuteration.

When deuterium is substituted in the anthracene derivative compound in the present invention, the degree of deuteration thereof is the carbon atom in the anthracene derivative relative to the sum of all hydrogens directly bonded to carbon atoms in the anthracene derivative and all deuterium directly bonded to carbon atoms in the anthracene derivative. It means that the ratio of all deuterium directly bonded to is expressed as a percentage.

For example, in the case of an anthracene derivative represented by the following compound Z, since there are 5 deuteriums in the phenyl group bonded to the anthracene group and 5 deuteriums in the phenyl group bonded to dibenzofuran, there are 10 deuteriums in total, and the anthracene group has 8 hydrogen atoms. 6 hydrogen atoms bonded to aromatic carbon atoms in both 6-membered rings of dibenzofuran are bonded, and the degree of deuteration thereof can be expressed as 100*10/(10+8+6) = 41.7%.

[화합물 Z]

[Compound Z]

On the other hand, in the case of a specific substituent, since the degree of deuteration may be different for each individual substituent, the degree of deuteration may be expressed by calculating the average degree of substitution.

As an example, considering the case of an anthracene group partially substituted with deuterium, an anthracene derivative in which deuterium is bonded to all carbon atoms may be prepared according to reaction conditions and used as a deuterium-substituted anthracene group, but depending on the reaction conditions Accordingly, a product in which a compound in which hydrogen is bonded to a carbon atom(s) at a specific position or a specific moiety and a compound in which deuterium is bonded may be obtained in the form of a mixture, and it may be very difficult to separate them, In this case, you can calculate the degree of deuterium substitution according to the overall structural formula by obtaining the average degree of substitution of deuterium.

In the present invention, by using the anthracene derivative substituted with deuterium as described above among the anthracene derivatives represented by the above [Formula E], the lifespan of the organic light emitting diode can be further improved.

The anthracene derivative represented by [Formula E] in the organic light emitting device according to the present invention may be any one selected from the following <Compound 201> to <Compound 506>.

<Compound 201> <Compound 202> <Compound 203>

<Compound 204> <Compound 205> <Compound 206>

<Compound 207> <Compound 208> <Compound 209>

<Compound 210> <Compound 211> <Compound 212>

<Compound 213> <Compound 214> <Compound 215>

<Compound 216> <Compound 217> <Compound 218>

<Compound 219> <Compound 220> <Compound 221>

<Compound 222> <Compound 223> <Compound 224>

<Compound 225> <Compound 226> <Compound 227>

<Compound 228> <Compound 229> <Compound 230>

<Compound 231> <Compound 232> <Compound 233>

<Compound 234> <Compound 235> <Compound 236>

<Compound 237> <Compound 238> <Compound 239>

<Compound 240> <Compound 241> <Compound 242>

<Compound 243> <Compound 244> <Compound 245>

<Compound 246> <Compound 247> <Compound 248>

<Compound 249> <Compound 250> <Compound 251>

<Compound 252> <Compound 253> <Compound 254>

<Compound 255> <Compound 256> <Compound 257>

<Compound 258> <Compound 259> <Compound 260>

<Compound 261> <Compound 262> <Compound 263>

<Compound 264> <Compound 265> <Compound 266>

<Compound 267> <Compound 268> <Compound 269>

<Compound 270> <Compound 271> <Compound 272>

<Compound 273> <Compound 274> <Compound 275>

<Compound 276> <Compound 277> <Compound 278>

<Compound 279> <Compound 280> <Compound 281>

<Compound 282> <Compound 283> <Compound 284>

<Compound 285> <Compound 286> <Compound 287>

<Compound 288> <Compound 289> <Compound 290>

<Compound 291> <Compound 292> <Compound 293>

<Compound 294> <Compound 295> <Compound 296>

<Compound 297> <Compound 298> <Compound 299>

<Compound 300> <Compound 301> <Compound 302>

<Compound 303> <Compound 304> <Compound 305>

<Compound 306> <Compound 307> <Compound 308>

<Compound 309> <Compound 310> <Compound 311>

<Compound 312> <Compound 313> <Compound 314>

<Compound 315> <Compound 316> <Compound 317>

<Compound 318> <Compound 319> <Compound 320>

<Compound 321> <Compound 322> <Compound 323>

<Compound 324> <Compound 325> <Compound 326>

<Compound 327> <Compound 328> <Compound 329>

<Compound 330> <Compound 331> <Compound 332>

<Compound 333> <Compound 334> <Compound 335>

<Compound 336> <Compound 337> <Compound 338>

<Compound 339> <Compound 340> <Compound 341>

<Compound 342> <Compound 343> <Compound 344>

<Compound 345> <Compound 346> <Compound 347>

<Compound 348> <Compound 349> <Compound 350>

<Compound 351> <Compound 352> <Compound 353>

<Compound 354> <Compound 355> <Compound 356>

<Compound 357> <Compound 358> <Compound 359>

<Compound 360> <Compound 361> <Compound 362>

<Compound 363> <Compound 364> <Compound 365>

<Compound 366> <Compound 367> <Compound 368>

<Compound 369> <Compound 370> <Compound 371>

<Compound 372> <Compound 373> <Compound 374>

<Compound 375> <Compound 376> <Compound 377>

<Compound 378> <Compound 379> <Compound 380>

<Compound 381> <Compound 382> <Compound 383>

<Compound 384> <Compound 385> <Compound 386>

<Compound 387> <Compound 388> <Compound 389>

<Compound 390> <Compound 391> <Compound 392>

<Compound 393> <Compound 394> <Compound 395>

<Compound 396> <Compound 397> <Compound 398>

<Compound 399> <Compound 400> <Compound 401>

<Compound 402> <Compound 403> <Compound 404>

<Compound 405> <Compound 406> <Compound 407>

<Compound 408> <Compound 409> <Compound 410>

<Compound 411> <Compound 412> <Compound 413>

<Compound 414> <Compound 415> <Compound 416>

<Compound 417> <Compound 418> <Compound 419>

<Compound 420> <Compound 421> <Compound 422>

<Compound 423> <Compound 424> <Compound 425>

<Compound 426> <Compound 427> <Compound 428>

<Compound 429> <Compound 430> <Compound 431>

<Compound 432> <Compound 433> <Compound 434>

<Compound 435> <Compound 436> <Compound 437>

<Compound 438> <Compound 439> <Compound 440>

<Compound 441> <Compound 442> <Compound 443>

<Compound 444> <Compound 445> <Compound 446>

<Compound 447> <Compound 448> <Compound 449>

<Compound 450> <Compound 451> <Compound 452>

<Compound 453> <Compound 454> <Compound 455>

<Compound 456> <Compound 457> <Compound 458>

<Compound 459> <Compound 460> <Compound 461>

<Compound 462> <Compound 463> <Compound 464>

<Compound 465> <Compound 466> <Compound 467>

<Compound 468> <Compound 469> <Compound 470>

<Compound 471> <Compound 472> <Compound 473>

<Compound 474> <Compound 475> <Compound 476>

<Compound 477> <Compound 478> <Compound 479>

<Compound 480> <Compound 481> <Compound 482>

<Compound 483> <Compound 484> <Compound 485>

<Compound 486> <Compound 487> <Compound 488>

<Compound 489> <Compound 490> <Compound 491>

<Compound 492> <Compound 493> <Compound 494>

<Compound 495> <Compound 496> <Compound 497>

<Compound 498> <Compound 499> <Compound 500>

<Compound 501> <Compound 502> <Compound 503>

<Compound 504> <Compound 505> <Compound 506>

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

1 is a diagram illustrating a 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 a first light emitting layer 50-A and a second light emitting layer (50-A) including an anode 20, a hole transport layer 40, a host and a dopant ( 50-B), an electron transport layer 60 and an organic light emitting device comprising a cathode 80 in sequential order, wherein the anode is a first electrode and the cathode is a second electrode, a hole transport layer between the anode and the light emitting layer and corresponds to an organic light emitting device including an electron transport layer between the light emitting layer and the cathode.

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

Referring to FIG. 1, the organic light emitting device of the present invention and a manufacturing method thereof will be described as follows.

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

A hole injection layer 30 is formed by vacuum thermal evaporation 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 the 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, 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 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) may be used. However, the present invention is not necessarily limited thereto.

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

Subsequently, the first light-emitting layer 50-A and the second light-emitting layer 50-B may be sequentially stacked on the hole transport layer 40 or the electron blocking layer by a vacuum deposition method or a spin coating method.

Here, each of the first light-emitting layer and the second light-emitting layer may be formed of a host and a dopant, and materials constituting them are as described above.

That is, the light-emitting layer is a first light-emitting layer (50-A) and a second light-emitting layer (50-B) using the same or different host and dopant materials through a separate deposition process or coating process, respectively, the first light-emitting layer and Each of the second light emitting layers may be formed.

More preferably, the first light emitting layer includes at least one compound represented by Formula A or Formula B as a fluorescent host, and the second light emitting layer includes at least one anthracene derivative represented by Formula E. In addition, as each of the fluorescent dopants in the first light emitting layer and the second light emitting layer, any one or more materials selected from Chemical Formulas D1 to D10 may be used as the same or different materials independently of each other.

In addition, as a host material usable in the first light-emitting layer and the second light-emitting layer in the present invention, the host material (BH1) used in the first light-emitting layer is the lowest unoccupied molecule compared to the host material (BH2) used in the second light-emitting layer. By using a material having a lower orbital function (LUMO) and a higher molecular orbital function (HOMO), injection of holes and/or electrons compared to the host (BH2) used in the second light emitting layer It is desirable to have this easy structure.

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

In addition, in the present invention, The deposition thickness ratio of the first light emitting layer (including the compound represented by Formula A or B) and the second light emitting layer (including the anthracene derivative represented by Formula E) is 100 when the sum of the thicknesses of the first light emitting layer and the second light emitting layer is 100 The thickness of the first light emitting layer may be preferably in the range of 10% to 70%, and more preferably in the range of 20% to 50%.

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 may be used as it functions to stably transport electrons injected from an electron injection electrode (Cathode). Examples of known electron transport materials include quinoline derivatives, in particular tris(8-quinolinolate)aluminum (Alq ₃ ), Liq, TAZ, BAlq, beryllium bis(benzoquinolin-10-noate) (beryllium bis(benzoquinolin) Materials such as -10-olate: Bebq2), E 201, E 202, BCP, and oxadiazole derivatives PBD, BMD, BND, etc. may be used, but the present invention is not limited thereto.

TAZ BALQ

E 201 E 202 BCP

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

As the material for forming the electron injection layer, any known material for forming the electron injection layer such as CsF, NaF, LiF, Li ₂ O, and BaO may be used. Although the deposition conditions of the electron injection layer vary depending on the compound used, in general, the electron injection layer may be selected from the same range of conditions as those of the hole injection layer.

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

In addition, in the present invention, the cathode may use a material having a small work function 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) or the like, or a transmissive 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 that emits 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 additionally formed light emitting layer may be a fluorescent material or a phosphorescent material.

Also, in the present invention, one or more layers selected from each of the above layers may be formed by a monomolecular deposition process or a solution process.

Here, the deposition process means 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 mixing a material used as a material for a solvent and forming a thin film through 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 flat-panel lighting, either monochromatic or white; and a monochromatic or white flexible lighting device; may be used in any one device selected from the group consisting of:

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

(Example)

<Preparation of host compound>

Synthesis Example 1. Synthesis of Formula 19

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

[Scheme 1]

<1-a>

A 3000 ml round-bottom flask was purged with nitrogen, and 1,6-dibromopyrene 100 g (0.278 mol), phenylboronic acid 33.9 g (0.278 mol), tetrakistriphenylphosphinepalladium (Pd[PPh ₃ ] ₄ ) 6.4 g (0.006 mol), 88.3 g (0.833 mol) of sodium carbonate, 1400 ml of toluene and 420 ml of water are added and refluxed for 9 hours. Upon completion of the reaction, the resulting solid is filtered and discarded after cooling to room temperature, the filtrate is extracted with ethyl acetate and water, and the organic layer is anhydrous. After anhydrous treatment, concentration under reduced pressure, and separation by column chromatography to obtain <1-a> 45.4 g (yield 45.7%).

Synthesis Example 1-2. Synthesis of <1-b>

[Scheme 2]

<1-b>

A 500 ml round bottom flask was purged with nitrogen, and 6-bromo-1-dibenzofuranol 20 g (0.076 mol), phenylboronic acid (D5) 11.6 g (0.091 mol), tetrakistriphenylphosphinepalladium (Pd[ PPh ₃ ] ₄ ) 1.8 g (0.002 mol), 17.9 g (0.129 mol) of potassium carbonate, 140 ml of toluene, 35 ml of ethanol, and 65 ml of water are added and refluxed for 5 hours. Upon completion of the reaction, after cooling to room temperature, extraction is performed with ethyl acetate and water, and the organic layer is anhydrous. The organic layer was concentrated under reduced pressure and recrystallized from ethyl acetate and heptane to obtain 15.2 g (yield 75.4%) of <1-b>.

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

[Scheme 3]

<1-c>

A 500 ml round-bottom flask is purged with nitrogen, and <1-b> 15.2 g (0.058 mol), 6 g (0.076 mol) of pyridine, and 150 ml of dichloromethane are added, and the temperature is cooled to 0 °C or less. After cooling, 18.1 g (0.064 mol) of trifluoromethane sulfonic anhydride is slowly added dropwise. After the dropwise addition, the reaction solution is heated to room temperature and stirred until the reaction is complete. Upon completion of the reaction, the mixture was extracted with dichloromethane and water, the organic layer was anhydrous, distilled under reduced pressure, and separated by column chromatography to obtain <1-c> 20 g (yield 87.3%).

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

[Scheme 4]

<1-d>

A 300 ml round-bottom flask was purged with nitrogen and <1-c> 20 g (0.050 mol), 16.6 g (0.065 mol) of bispinacol diboron, 0.8 g (0.001 mol) of bisdiphenylphosphinoferrocenedichloropalladium (0.001 mol), calcium acetate 9.9 g (0.101 mol) and 200 ml of 1,4-dioxane are added and refluxed for 12 hours. When the reaction was completed, the reaction solution was cooled to room temperature, filtered through Celite, and the filtrate was concentrated and separated by column chromatography to obtain 14.8 g (yield 78.4%) of <1-d>.

Synthesis Example 1-5. Synthesis of [Formula 19]

[Scheme 5]

[Formula 19]

A 300 ml round-bottom flask was purged with nitrogen and <1-a> 10.7 g (0.030 mol), <1-d> 13.7 g (0.036 mol), tetrakistriphenylphosphine palladium 0.7 g (0.001 mol), potassium carbonate 7.4 g (0.053 mol), 80 ml of toluene, 20 ml of ethanol, and 26 ml of water are added and refluxed for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted with ethyl acetate and water. After anhydrous treatment, the organic layer was concentrated and separated by column chromatography to obtain 8.4 g (yield 53.4%) of [Formula 19].

MS(MALDI-TOF) : m/z 525.21[M] ⁺

Synthesis Example 2. Synthesis of Formula 34

Synthesis Example 2-1. Synthesis of <2-a>

[Scheme 6]

<2-a>

<2-a> (yield 79.3%) was obtained by synthesis in the same manner except that phenylboronic acid (D5) was used instead of phenylboronic acid used in Synthesis Example 1-1.

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

[Scheme 7]

<2-b>

6-bromo-1-dibenzofuranol used in Synthesis Example 1-2 Instead, <2-b> (yield 54%) was obtained by synthesizing in the same manner except that 1,7-dibromodibenzofuran was used.

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

[Scheme 8]

<2-c>

<2-c> (yield 72.8%) was obtained by synthesis in the same manner except that <2-b> was used instead of <1-c> used in Synthesis Example 1-4.

Synthesis Example 2-4. Synthesis of [Formula 34]

[Scheme 9]

[Formula 34]

[Formula 34] (Yield) 63.7%) was obtained.

MS(MALDI-TOF) : m/z 530.25[M] ⁺

Synthesis Example 3. Synthesis of Formula 52

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

[Scheme 10]

<3-a>

6-bromo-1-dibenzofuranol used in Synthesis Example 1-2 Instead, 6-bromo-2-dibenzofuranol was used, and <3-a> (yield 72.0%) was obtained by the same method except that phenylboronic acid was used instead of phenylboronic acid (D5).

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

[Scheme 11]

<3-b>

<3-b> (yield 85.2%) was obtained in the same manner except that <3-a> was used instead of <1-b> used in Synthesis Example 1-3.

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

[Scheme 12]

<3-c>

<3-c> (yield 76.8%) was obtained by synthesizing in the same manner except that <3-b> was used instead of <1-c> used in Synthesis Example 1-4.

Synthesis Example 3-4. Synthesis of [Formula 52]

[Scheme 13]

[Formula 52]

In Synthesis Example 2-4, except that <3-c> was used instead of <2-c>, it was synthesized in the same manner to obtain [Formula 52] (yield 58.0%).

MS(MALDI-TOF) : m/z 525.21[M] ⁺

Synthesis Example 4. Synthesis of Formula 131

Synthesis Example 4-1. Synthesis of [Formula 131]

[Scheme 14]

[Formula 131]

In Synthesis Example 2-4, except that 1-dibenzofuranboronic acid was used instead of <2-c>, it was synthesized in the same manner to obtain [Formula 131] (yield 61.4%).

MS(MALDI-TOF): m/z 449.18[M] ⁺

Synthesis Example 5. Synthesis of Chemical Formula 136

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

[Scheme 15]

<5-a>

A 1000 ml round-bottom flask was purged with nitrogen, and 50 ml (0.477 mol) of a 30wt% aqueous solution of hydrogen peroxide, 45 g (0.454 mol) of phenol (D5), 57.6 g (0.227 mol) and 450 ml of water were added and heated at 50 °C for 24 hours. time to stir. When the reaction is complete, an aqueous sodium thiosulfate solution is added, stirred, and the reaction solution is extracted with ethyl acetate and water, treated anhydrous, and concentrated under reduced pressure. After concentration, it was separated by column chromatography to obtain <5-a> 45 g (yield 44.3%).

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

[Scheme 16]

<5-b>

A 1000 ml round bottom flask was purged with nitrogen and <5-a> 45 g (0.201 mol), 2-fluoro-6-methoxyphenylboronic acid 41 g (0.241 mol), tetrakistriphenylphosphine palladium 7 g ( 0.006 mol), potassium carbonate 47.2 g (0.341 mol), toluene 315 ml, ethanol 80 ml and water 170 ml, and reflux for 8 hours. Upon completion of the reaction, the mixture is cooled to room temperature, extracted with ethyl acetate and water, and the organic layer is anhydrous. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 28.6 g of <5-b> (yield 64.1%).

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

[Scheme 17]

<5-c>

In a 500 ml round-bottom flask, 28.6 g (0.129 mol) of <5-b>, 44.5 g (0.322 mol) of potassium carbonate, and 143 ml of 1-methyl-2-pyrrolidine were put and refluxed for 12 hours. After completion of the reaction, after cooling to room temperature, 200 ml of 2 N-hydrochloric acid solution is slowly added, and after sufficient stirring, the mixture is extracted with ethyl acetate and water. The organic layer was concentrated and separated by column chromatography to obtain <5-c> 21 g (yield 80.7%).

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

[Scheme 18]

<5-d>

In a 500 ml round-bottom flask, put 21 g (0.104 mol) of <5-c> and 120 ml of dichloromethane, and cool the reaction solution to 0 °C or less. 52 g (0.208 mol) of borontribromide is slowly added dropwise, paying attention to the temperature. After the dropwise addition, the reaction solution is heated to room temperature and stirred until completion of the reaction. When the reaction is completed, 100 ml of water is slowly added dropwise to the reaction solution, and then sufficiently stirred. The reaction solution was extracted with dichloromethane and water, treated anhydrous, concentrated under reduced pressure, and separated by column chromatography to obtain 15 g of <5-d> (yield 76.8%).

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

[Scheme 19]

<5-e>

A 500 ml round-bottom flask was purged with nitrogen, and <5-d> 15.0 g (0.080 mol), 8.2 g (0.104 mol) of pyridine, and 150 ml of dichloromethane were added, and the temperature of the reaction solution was cooled to 0 °C or less. After cooling, 24.7 g (0.088 mol) of trifluoromethanesulfonic anhydride is slowly added dropwise. After the dropwise addition, the reaction solution was heated to room temperature and stirred until the reaction was completed. Upon completion of the reaction, the mixture was extracted with dichloromethane and water, the organic layer was anhydrous, concentrated under reduced pressure, and separated by column chromatography to obtain <5-e> 20 g (yield 78.4%).

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

[Scheme 20]

<5-f>

A 500 ml round-bottom flask was purged with nitrogen and <5-e> 20 g (0.062 mol), 23.8 g (0.094 mol) of bispinacoldiboron, 2.5 g (0.003 mol) of bisdiphenylphosphinoferrocenedichloropalladium, calcium acetate Add 9.5 g (0.125 mol) and 200 ml of 1,4-dioxane and reflux for 12 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature, filtered through Celite, and the filtrate was concentrated and separated by column chromatography to obtain 15 g (yield 80.6%) of <5-f>.

Synthesis Example 5-7. Synthesis of [Formula 136]

[Scheme 21]

[Formula 136]

In Synthesis Example 2-4, except that <5-f> was used instead of <2-c>, it was synthesized in the same manner as [Formula 136] (yield 60.3%) was obtained.

MS(MALDI-TOF) : m/z 453.21[M] ⁺

Synthesis Example 6. Synthesis of Formula 41

Synthesis Example 6-1. Synthesis of [Formula 41]

[Scheme 22]

[Formula 41]

It was synthesized in the same manner except that <2-a> was used instead of <1-a> used in Synthesis Example 1-5 to obtain [Formula 41] (yield 54.2%).

MS(MALDI-TOF) : m/z 530.25[M] ⁺

Synthesis Example 7. Synthesis of Chemical Formula 57

Synthesis Example 7-1. Synthesis of [Formula 57]

[Scheme 23]

[Formula 57]

It was synthesized in the same manner except that <3-c> was used instead of <1-d> used in Synthesis Example 1-5 to obtain [Formula 57] (yield 53.5%).

MS(MALDI-TOF) : m/z 520.18[M] ⁺

<Preparation of dopant compound>

Synthesis Example 8. Synthesis of D202

Synthesis Example 8-1. Synthesis of <8-a>

[Scheme 24]

<8-a>

In a 100 mL reactor, 3.1 g (16 mmol) of 1-bromo-3-chlorobenzene, 5.8 g (16 mmol) of aniline, 0.1 g (1 mmol) of palladium acetate, 3 g (32 mmol) of sodium tert-butoxide, bis 0.2 g (1 mmol) of (diphenylphosphino)-1,1'-binaphthyl and 45 mL of toluene are added, and the mixture is stirred under reflux for 24 hours. After the reaction was completed, the filtrate was concentrated by filtration and separated by column chromatography to obtain 5.2 g of <8-a>. (Yield 82%)

Synthesis Example 8-2. Synthesis of <8-b>

[Scheme 25]

<8-b>

In a 250 mL reactor, 20 g (98 mmol) of <8-a>, 20.9 g (98 mmol) of 3-bromobenzothiophene, 0.5 g (2 mmol) of palladium acetate, 18.9 g (196 mmol) of sodium tert-butoxide , 0.8 g (4 mmol) of tri-tert-butylphosphine and 200 mL of toluene are added, and the mixture is stirred under reflux for 5 hours. After completion of the reaction, the filtrate was concentrated by filtration and separated by column chromatography to obtain 24.7 g of <8-b>. (yield 75%)

Synthesis Example 8-3. Synthesis of <8-c>

[Scheme 26]

<8-c>

In a 100 mL reactor, 5.4 g (16 mmol) of <8-b>, 5.8 g (16 mmol) of aniline, 0.1 g (1 mmol) of palladium acetate, 3 g (32 mmol) of sodium tert-butoxide, and bis(diphenylphos) Pino)-1,1'-binaphthyl 0.2 g (1 mmol) and toluene 45 mL are added, and the mixture is stirred under reflux for 24 hours. After completion of the reaction, the filtrate was concentrated by filtration and separated by column chromatography to obtain 4.6 g of <8-c>. (Yield 73%)

Synthesis Example 8-4. Synthesis of <8-d>

[Scheme 27]

<8-d>

Synthesis in the same manner except that <8-c> was used instead of <8-a> used in Synthesis Example 8-2 and 1-bromo-2-iodobenzene was used instead of 3-bromobenzothiophene Thus, <8-d> was obtained. (yield 77%)

Synthesis Example 8-5. Synthesis of <D 202>

[Scheme 28]

<D 202>

In a 300 mL reactor, put 12.6 g (23 mmol) of <8-d> and 120 mL of tert-butylbenzene. At -78°C, 42.5 mL (68 mmol) of n-butyllithium is added dropwise. After dropwise addition, the mixture was stirred at 60°C for 3 hours. After that, the heptane is removed by blowing nitrogen at 60 °C. 11.3 g (45 mmol) of boron tribromide is added dropwise at -78°C. After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and 5.9 g (45 mmol) of N,N-diisopropylethylamine was added dropwise at 0°C. After dropwise addition, the mixture was stirred at 120 °C for 2 hours. After completion of the reaction, an aqueous sodium acetate solution was added at room temperature and stirred. After extraction with ethyl acetate, the organic layer was concentrated and separated by column chromatography to obtain 1.1 g of <D202>. (yield 10%)

MS (MALDI-TOF): m/z 476.15 [M ⁺ ]

Synthesis Example 9. Synthesis of D 265

Synthesis Example 9-1. Synthesis of <9-a>

[Scheme 29]

<9-a>

<9-a> was obtained in the same manner as in Synthesis Example 8-1, except that 1-bromo-2,3-dichlorobenzene was used instead of 1-bromo-3-chlorobenzene. (Yield 71%)

Synthesis Example 9-2. Synthesis of <9-b>

[Scheme 30]

<9-b>

Synthesis in the same manner except that diphenylamine was used instead of <8-a> used in Synthesis Example 8-2 and 1-bromo-3-iodobenzene was used instead of 1-bromo-3-chlorobenzene Thus, <9-b> was obtained. (yield 77%)

Synthesis Example 9-3. Synthesis of <9-c>

[Scheme 31]

<9-c>

<9-a> was used instead of <8-a> used in Synthesis Example 8-2, and <9-b> was used instead of 1-bromo-3-chlorobenzene. -c> was obtained. (yield 75%)

Synthesis Example 9-4. Synthesis of <9-d>

[Scheme 32]

<9-d>

In a 1 L reactor, 30 g (174 mmol) of 3-bromoaniline, 25.5 g (209 mmol) of phenylbronic acid, 4 g (3 mmol) of tetrakis(triphenylphosphine)palladium, 48.2 g (349 mmol) of potassium carbonate , Add 150 mL of 1,4-dioxane, 150 mL of toluene, and 90 mL of distilled water, and stir under reflux for 4 hours. After completion of the reaction, the layers were separated at room temperature, the organic layer was concentrated under reduced pressure, and then separated by column chromatography to obtain <9-d> 24 g. (yield 80%)

Synthesis Example 9-5. Synthesis of <9-e>

[Scheme 33]

<9-e>

<9-e> was synthesized in the same manner as in Synthesis Example 8-1, except that 3-bromobenzofuran was used instead of 1-bromo-3-chlorobenzene and <9-d> was used instead of aniline. got it (Yield 68%)

Synthesis Example 9-6. Synthesis of <9-f>

[Scheme 34]

<9-f>

<9-c> was used instead of <8-a> used in Synthesis Example 8-2, and <9-e> was used instead of 1-bromo-3-chlorobenzene. -f> was obtained. (Yield 68%)

Synthesis Example 9-7. Synthesis of <D 265>

[Scheme 35]

<D 265>

In a 250 mL reactor, put 21 g (37 mmol) of <9-f>, tert-butylbenzene. At -78 °C, 42.4 mL (74 mmol) of tertiary butyl lithium is added dropwise. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Thereafter, nitrogen is blown at 60 °C to remove pentane. At -78 °C, 7.1 mL (74 mmol) of boron tribromide is added dropwise. After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and 6 g (74 mmol) of N,N-diisopropylethylamine was added dropwise at 0°C. After dropwise addition, the mixture was stirred at 120 °C for 2 hours. After completion of the reaction, an aqueous sodium acetate solution was added at room temperature and stirred. After extraction with ethyl acetate, the organic layer was concentrated and separated by column chromatography to obtain <D 265> 2.0 g. (Yield 17%)

MS (MALDI-TOF): m/z 703.28 [M ⁺ ]

Synthesis Example 10. Synthesis of Formula D 459

Synthesis Example 10-1. Synthesis of <10-a>

[Scheme 36]

<10-a>

4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole was used instead of <8-a> used in Synthesis Example 8-2, and 3-bromobenzothiophene was used instead of <10-a> was obtained by synthesis in the same manner except that 1-bromo-2,3-dichloro-5-methylbenzene was used. (Yield 32%)

Synthesis Example 10-2. Synthesis of <10-b>

[Scheme 37]

<10-b>

<10-b> was obtained in the same manner as in Synthesis Example 8-1, except that 3-(1-naphthyl)-1-bromobenzene was used instead of 1-bromo-3-chlorobenzene. (yield 77%)

Synthesis Example 10-3. Synthesis of <10-c>

[Scheme 38]

<10-c>

Synthesis in the same manner except that <10-b> was used instead of <8-a> used in Synthesis Example 8-2 and 1-bromo-3-iodobenzene was used instead of 3-bromobenzothiophene Thus, <10-c> was obtained. (Yield 64%)

Synthesis Example 10-4. Synthesis of <10-d>

[Scheme 39]

<10-d>

<10-d> was obtained by the same method as in Synthesis Example 8-1, except that <10-c> was used instead of 1-bromo-3-chlorobenzene. (yield 75%)

Synthesis Example 10-5. Synthesis of <10-e>

[Scheme 40]

<10-e>

<10-e was synthesized in the same manner except that <10-d> was used instead of <8-a> used in Synthesis Example 8-2 and <10-a> was used instead of 3-bromobenzothiophene > was obtained. (Yield 65%)

Synthesis Example 10-6. Synthesis of <D 459>

[Scheme 41]

<D 459>

<D459> was obtained by synthesizing in the same manner except that <10-e> was used instead of <9-f> used in Synthesis Example 9-7. (Yield 11%)

MS (MALDI-TOF): m/z 759.38 [M ⁺ ]

Examples 1 to 46: Preparation of an organic light emitting device including a first light emitting layer and a second light emitting layer

The light emitting area of the ITO glass was patterned to have a size of 2 mm x 2 mm and then washed. After the ITO glass was mounted in a vacuum chamber and the base pressure was set to 1x10 ^-7 torr, a film was formed on the ITO in order of DNTPD (700 Å) and α-NPD (300 Å). In the light emitting layer, a first light emitting layer and a second light emitting layer are sequentially formed, but the first light emitting layer is a pyrene compound (compound represented by Formula A or Formula B) according to the present invention and the following BD dopant compound (1 wt%) mixed to form a film (50 Å), and the second light emitting layer is formed by mixing an anthracene compound (compound represented by Formula E) according to the present invention and the following BD dopant compound (1 wt%) (150 Å), and then the electron transport layer [E-1] and [E-2] as (1:1) ratio (300Å), as an electron injection layer [E-2] (10Å), Al (1,000Å) by forming a film in the order of the organic light emitting device was prepared. The emission characteristics of the organic light emitting device were measured at 0.4 mA.

[DNTPD] [α-NPD]

[E-1] [E-2]

first light emitting layer second light emitting layer EQE T97 V host dopant host dopant Example 1 Formula 19 D 202 compound 219 D 202 13.0 315 3.6 Example 2 Formula 19 D 202 compound 307 D 202 13.6 320 3.8 Example 3 Formula 19 D 202 compound 433 D 202 13.2 308 3.7 Example 4 Formula 34 D 202 compound 254 D 202 12.7 301 3.7 Example 5 Formula 34 D 202 compound 307 D 202 12.9 312 3.8 Example 6 Formula 34 D 202 compound 433 D 202 12.4 300 3.6 Example 7 Formula 52 D 202 compound 219 D 202 12.6 309 3.6 Example 8 Formula 52 D 202 compound 254 D 202 13.0 314 3.7 Example 9 Formula 52 D 202 compound 307 D 202 13.3 305 3.7 Example 10 Formula 131 D 202 compound 219 D 202 13.0 311 3.6 Example 11 Formula 131 D 202 compound 254 D 202 12.5 307 3.8 Example 12 Formula 131 D 202 compound 433 D 202 12.6 300 3.8 Example 13 Formula 136 D 202 compound 219 D 202 12.6 306 3.6 Example 14 Formula 136 D 202 compound 307 D 202 12.8 311 3.7 Example 15 Formula 136 D 202 compound 433 D 202 12.1 302 3.7 Example 16 Formula 19 D 265 compound 219 D 265 12.8 281 3.6 Example 17 Formula 19 D 265 compound 307 D 265 13.2 295 3.6 Example 18 Formula 19 D 265 compound 433 D 265 12.5 290 3.6 Example 19 Formula 34 D 265 compound 254 D 265 11.9 280 3.8 Example 20 Formula 34 D 265 compound 307 D 265 12.3 283 3.8 Example 21 Formula 34 D 265 compound 433 D 265 11.8 287 3.8 Example 22 Formula 52 D 265 compound 219 D 265 12.7 291 3.8 Example 23 Formula 52 D 265 compound 254 D 265 11.9 292 3.7 Example 24 Formula 52 D 265 compound 307 D 265 11.6 288 3.7 Example 25 Formula 131 D 265 compound 219 D 265 12.4 284 3.8 Example 26 Formula 131 D 265 compound 254 D 265 12.1 280 3.8 Example 27 Formula 131 D 265 compound 433 D 265 11.9 290 3.6 Example 28 Formula 136 D 265 compound 219 D 265 11.8 286 3.8 Example 29 Formula 136 D 265 compound 307 D 265 12.0 294 3.8 Example 30 Formula 136 D 265 compound 433 D 265 11.5 290 3.7 Example 31 Formula 19 D 459 compound 219 D 459 12.0 286 3.8 Example 32 Formula 19 D 459 compound 307 D 459 12.5 300 3.7 Example 33 Formula 52 D 459 compound 254 D 459 11.9 295 3.6 Example 34 Formula 52 D 459 compound 307 D 459 11.6 280 3.7 Example 35 Formula 136 D 459 compound 307 D 459 12.0 292 3.8 Example 36 Formula 136 D 459 compound 433 D 459 11.5 288 3.7 Example 37 Formula 41 D 202 compound 403 D 202 14.2 345 3.6 Example 38 Formula 41 D 459 compound 403 D 459 14.0 330 3.6 Example 39 chemical formula 57 D 202 compound 403 D 202 11.9 264 3.8 Example 40 Formula 41 D 202 compound 486 D 202 13.9 327 3.6 Example 41 Formula 41 D 202 compound 498 D 202 13.8 324 3.7 Example 42 Formula 19 D 202 compound 461 D 202 11.9 292 3.7 Example 43 chemical formula 57 D 202 compound 461 D 202 11.4 260 3.8 Example 44 Formula 34 D 202 compound 463 D 202 11.7 262 3.7 Example 45 Formula 41 d 98 compound 403 d 141 13.6 318 3.7 Example 46 Formula 19 D 202 compound 498 D 459 12.7 305 3.7

Comparative Examples 1 to 18

The organic light emitting device for Comparative Examples 1 to 18 was prepared in the same manner except that the compounds described in the following table were used in addition to the compounds used in the first light emitting layer and the second light emitting layer of Examples 1 to 46, and the organic light emitting device was prepared. The light emitting characteristics of the light emitting device were measured at 0.4 mA.

first light emitting layer second light emitting layer EQE T97 V host dopant host dopant Comparative Example 1 Formula 19 D 202 Formula 34 D 202 8.7 190 4.0 Comparative Example 2 Formula 52 D 265 Formula 131 D 265 8.5 185 4.1 Comparative Example 3 BH1 D 202 Formula 19 D 202 7.7 180 4.0 Comparative Example 4 BH1 D 265 Formula 34 D 265 7.4 180 4.0 Comparative Example 5 BH1 D 202 BH1 D 202 6.5 170 4.2 Comparative Example 6 BH1 D 459 BH1 D 459 6.3 160 4.0 Comparative Example 7 compound 219 D 202 BH2 D 202 7.6 185 3.9 Comparative Example 8 compound 307 D 265 BH2 D 265 7.3 178 3.8 Comparative Example 9 compound 219 D 202 compound 433 D 202 8.4 194 3.8 Comparative Example 10 compound 307 D 265 compound 254 D 265 8.0 182 3.9 Comparative Example 11 BH2 D 202 BH2 D 202 5.9 175 4.0 Comparative Example 12 BH2 D 459 BH2 D 459 5.6 170 4.0 Comparative Example 13 Formula 19 D 202 BH2 D 202 7.7 184 3.9 Comparative Example 14 Formula 131 D 265 BH2 D 265 7.5 179 3.9 Comparative Example 15 BH1 D 202 compound 307 D 202 9.4 210 3.8 Comparative Example 16 BH1 D 265 compound 433 D 265 8.9 200 3.8 Comparative Example 17 BH1 D 202 BH2 D 202 6.1 182 4.0 Comparative Example 18 BH1 D 459 BH2 D 459 5.8 175 4.0

[BH1] [BH2]

As shown in Tables 1 and 2, the organic light emitting device according to the present invention has superior luminous efficiency than the organic light emitting device using the compounds of Comparative Examples according to the prior art, and exhibits low voltage driving and long life characteristics. It can be seen that the applicability is high.

Claims (24)

a first electrode; and
a second electrode opposite the first electrode; includes,
a first light emitting layer including a first host and a first dopant between the first electrode and the second electrode; and a second light emitting layer including a second host and a second dopant;
At least one of the first host and the second host is an organic light emitting diode comprising at least one compound represented by the following [Formula A] or [Formula B].

[Formula A] [Formula B]

In the [Formula A] and [Formula B],
Wherein R ₁ to R ₁₄ are the same or different, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted A cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted 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, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, a halogen group any one selected from;
The linking groups L ₁ and L ₂ are the same or different from each other, and are each independently 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, and ;
Wherein n1 and n2 are each the same or different, and each independently an integer of 0 to 2, when each of them is 2, each linking group L ₁ and L ₂ are the same or different from each other,
Wherein R and R' are the same or different, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C 3 to 30 cycloalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C2 to C50 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine group, substituted or an unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, or a halogen group. any one selected;
Wherein n3 and n4 are each the same or different, and independently of each other are integers of 1 to 9, but when each of them is 2 or more, each R and R' are the same or different from each other, and

In [Formula A] and [Formula B], 'substitution' in 'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, and 1 to 24 carbon atoms. Halogenated alkyl group, C1-C24 alkenyl group, C1-C24 alkynyl group, C3-C24 cycloalkyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C7-C24 aryl group Alkyl group, C7-C24 alkylaryl group, C2-C24 heteroaryl group, C2-C24 heteroarylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C12-C24 Diarylamino group, diheteroarylamino group having 2 to 24 carbon atoms, aryl (heteroaryl)amino group having 7 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, arylsilyl group having 6 to 24 carbon atoms, aryl having 6 to 24 carbon atoms It means being 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,
The compound represented by Formula A contains at least one deuterium,
The compound represented by Formula B is an organic light emitting device, characterized in that it contains at least one deuterium.
3. The method of claim 2,
At least one of R ₁ to R ₇ in [Formula A] is a substituent containing deuterium,
At least one of R ₈ to R ₁₄ in the [Formula B] is an organic light emitting device, characterized in that it is a substituent containing deuterium.
3. The method of claim 2,
At least one R in [Formula A] is a substituent containing deuterium,
At least one R' in [Formula B] is an organic light emitting device, characterized in that it is a substituent containing deuterium.
The method of claim 1,
At least one of R ₁ to R ₇ in [Formula A] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms,
At least one of R ₈ to R ₁₄ in the [Formula B] is an organic light emitting device, characterized in that it is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.
The method of claim 1,
The linking groups L ₁ and L ₂ in Formulas A and B are each a single bond, or an organic light emitting device, characterized in that it is any one selected from the following [Structural Formula 1] to [Structural Formula 5].
[Structural formula 1] [Structural formula 2] [Structural formula 3]

[Structural formula 4] [Structural formula 5]

Hydrogen or deuterium may be bonded to the carbon site of the aromatic ring in the linking group.
7. The method of claim 6,
The connecting groups L ₁ and L ₂ are each an organic light emitting device, characterized in that a single bond.
The method of claim 1,
At least one R in [Formula A] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms,
At least one R' in [Formula B] is an organic light emitting device, characterized in that it is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.
9. The method of claim 8,
In Formulas A and B, n3 and n4 are each 1,
R in [Formula A] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms,
R' in [Formula B] is an organic light emitting device, characterized in that it is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.
The method of claim 1,
The organic compound represented by the [Formula A] or [Formula B] is An organic light emitting device, characterized in that the compound represented by any one of the following [Formula A-1] or [Formula B-1].
[Formula A-1] [Formula B-1]

In the [Formula A-1] and [Formula B-1],
The substituents R ₁ to R _{14, the} linking groups L ₁ and L ₂ , n1 and n2 are the same as defined in [Formula A] or [Formula B] in claim 1,
The substituents R and R' are substituted or unsubstituted aryl groups having 6 to 18 carbon atoms.
The method of claim 1,
In Formulas A and B, n3 and n4 are each 1,
At least one of R ₁ to R _{7 and} R in [Formula A] is an aryl group having 6 to 18 carbon atoms substituted with deuterium,
At least one of R ₈ to R _{14 and} R' in [Formula B] is an organic light emitting device, characterized in that it is an aryl group having 6 to 18 carbon atoms substituted with deuterium.
The method of claim 1,
In Formulas A and B, n3 and n4 are each 1,
R in [Formula A] is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms,
R' in [Formula B] is an organic light emitting device, characterized in that it is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.
The method of claim 1,
The compound is an organic light emitting device, characterized in that any one selected from the group represented by the following [Formula 1] to [Formula 240].

Formula 1 Formula 2 Formula 3

Formula 4 Formula 5 Formula 6

Formula 7 Formula 8 Formula 9

Formula 10 Formula 11 Formula 12

Formula 13 Formula 14 Formula 15

Formula 16 Formula 17 Formula 18

Formula 19 Formula 20 Formula 21

Formula 22 Formula 23 Formula 24

Formula 25 Formula 26 Formula 27

Formula 28 Formula 29 Formula 30

Formula 31 Formula 32 Formula 33

Formula 34 Formula 35 Formula 36

Formula 37 Formula 38 Formula 39

Formula 40 Formula 41 Formula 42

Formula 43 Formula 44 Formula 45

Formula 46 Formula 47 Formula 48

Formula 49 Formula 50 Formula 51

Formula 52 Formula 53 Formula 54

Formula 55 Formula 56 Formula 57

Formula 58 Formula 59 Formula 60

Formula 61 Formula 62 Formula 63

Formula 64 Formula 65 Formula 66

Formula 67 Formula 68 Formula 69

Formula 70 Formula 71 Formula 72

Formula 73 Formula 74 Formula 75

Formula 76 Formula 77 Formula 78

Formula 79 Formula 80 Formula 81

Formula 82 Formula 83 Formula 84

Formula 85 Formula 86 Formula 87 Formula

Formula 88 Formula 89 Formula 90

Formula 91 Formula 92 Formula 93 Formula 93

Formula 94 Formula 95 Formula 96

Formula 97 Formula 98 Formula 99

Formula 100 Formula 101 Formula 102

Formula 103 Formula 104 Formula 105

Formula 106 Formula 107 Formula 108

Formula 109 Formula 110 Formula 111

Formula 112 Formula 113 Formula 114

Formula 115 Formula 116 Formula 117 Formula

Formula 118 Formula 119 Formula 120

Chemical formula 121 Chemical formula 122 Chemical formula 123

Formula 124 Formula 125 Formula 126

Formula 127 Formula 128 Formula 129

Formula 130 Formula 131 Formula 132

Formula 133 Formula 134 Formula 135

Formula 136 Formula 137 Formula 138

Formula 139 Formula 140 Formula 141

Formula 142 Formula 143 Formula 144

Formula 145 Formula 146 Formula 147 Formula

Formula 148 Formula 149 Formula 150

Formula 151 Formula 152 Formula 153

Formula 154 Formula 155 Formula 156

Formula 157 Formula 158 Formula 159

Formula 160 Formula 161 Formula 162

Formula 163 Formula 164 Formula 165

Formula 166 Formula 167 Formula 168

Formula 169 Formula 170 Formula 171

Formula 172 Formula 173 Formula 174

Formula 175 Formula 176 Formula 177

Formula 178 Formula 179 Formula 180

Formula 181 Formula 182 Formula 183

Formula 184 Formula 185 Formula 186

Formula 187 Formula 188 Formula 189

Formula 190 Formula 191 Formula 192

Formula 193 Formula 194 Formula 195 Formula

Formula 196 Formula 197 Formula 198

Formula 199 Formula 200 Formula 201

Formula 202 Formula 203 Formula 204

Formula 205 Formula 206 Formula 207

Formula 208 Formula 209 Formula 210

Formula 211 Formula 212 Formula 213

Formula 214 Formula 215 Formula 216

Formula 217 Formula 218 Formula 219

Formula 220 Formula 221 Formula 222

Formula 223 Formula 224 Formula 225

Formula 226 Formula 227 Formula 228

Formula 229 Formula 230 Formula 231

Formula 232 Formula 233 Formula 234

Formula 235 Formula 236 Formula 237

Formula 238 Formula 239 Formula 240
According to claim 1,
At least one of a hole transport layer and a hole injection layer is provided between the first electrode and the first light emitting layer, and at least one of an electron transport layer and an electron injection layer is provided between the second light emitting layer and the second electrode organic light emitting device.
According to claim 1,
At least one of the first dopant in the first light emitting layer and the second dopant in the second light emitting layer is an organic light emitting device, characterized in that at least one compound selected from the following [Formula D1] to [Formula D10] is used.
[Formula D1]

[Formula D2]

In the [Formula D1] and [Formula D2], A ₃₁ , A ₃₂ , E ₁ and F ₁ are each the same or different, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or an unsubstituted aromatic heterocycle having 2 to 40 carbon atoms;
Two carbon atoms adjacent to each other in the aromatic ring of A ₃₁ and 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. to form;
The linking groups L ₂₁ to L ₃₂ are the same or different, and are each independently a single bond, a substituted or unsubstituted C 1 to C 60 alkylene group, a substituted or unsubstituted C 2 to C 60 alkenylene group, 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-C60 cycloalkylene group It is selected from an arylene group or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
wherein 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 , Ar ₂₁ to Ar ₂₈ are the same or different, and are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, or a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 of a cycloalkenyl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted an aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine having 1 to 30 carbon atoms group, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, 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 substituted or unsubstituted carbon number Any one selected from a 1 to 30 alkyl germanium group, a substituted or unsubstituted C 1 to C 30 aryl germanium group, a cyano group, a nitro group, and a halogen group,
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, S , Ge, Se, may be substituted with any 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 these is 2 or more, each of the connecting groups L ₂₁ to L ₃₂ is the same as or different from each other,
Wherein x1 is 1, y1, z1 and z2 are each the same or different, and are each independently an integer of 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;
In Formula D1, two carbon atoms adjacent to each other in ring A ₃₂ are combined with * in Formula Q ₁₁ to form a condensed ring,
In Formula D2, two adjacent carbon atoms in the A ₃₁ ring combine with * of the structural formula Q ₁₂ to form a condensed ring, and two adjacent carbon atoms in the A ₃₂ ring combine with the * in the structural formula Q ₁₁ Combined to form a condensed ring.

[Formula D3]

In the [Formula D3],
Wherein X ₁ is any one selected from B, P, P = O
wherein T1 to T3 are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocycle 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;
wherein R61 to R70 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted carbon number A 3 to 30 cycloalkyl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or An unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C5-C30 arylthioxy group, a substituted or unsubstituted C1-C30 alkylamine group, a 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 It may be combined with one or more rings selected from T1 to T3 to additionally form an alicyclic or aromatic monocyclic or polycyclic ring.

[Formula D4] [Formula D5]

In the [Formula D4] and [Formula D5],
Wherein X ₂ is any one selected from B, P, P = O
The 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]

Wherein X ₃ is any one selected from B, P, P = O
The 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 , R ₇₁ to R ₇₂ are each the same as R61 to R70 in [Formula D3],
R ₇₁ and R ₇₂ are each connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, or combine with the T ₇ or T ₉ ring to additionally form an alicyclic or aromatic monocyclic or polycyclic ring can do.

[Formula D8] [Formula D9]

[Formula D10]

In the [Formula D8] to [Formula D10],
Wherein X is any one selected from B, P, P = O,
The Q1 to Q3 are each the same as T ₁ to T ₃ in [Formula D3],
The linking group Y is any one selected from NR ₃ , CR4R5, O, S, and Se,
The substituents R3 to R5 are the same as those of R61 to R70 in [Formula D3], respectively,
The R ₃ to R ₅ may be combined with each of the Q ₂ ring or the Q ₃ ring to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,
The R ₄ and R ₅ may be connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,
The ring formed by 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 Cy1, substituted or unsubstituted carbon number 1 to 10 alkylene groups,
In the formula D9,
The '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 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, in Cy1 to which the nitrogen (N) atom is bonded Except for carbon atoms, it is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,
Here, the 'substitution' in the 'substituted or unsubstituted' in the [Formula D1] to [Formula D10] is deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, 1 carbon number to 24 halogenated alkyl group, C2-C24 alkenyl group, C2-C24 alkynyl group, C3-C24 cycloalkyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C7-C7 24 arylalkyl group, C7-C24 alkylaryl group, C2-C24 heteroaryl group, C2-C24 heteroarylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C12 A diarylamino group having to 24, a diheteroarylamino group having 2 to 24 carbon atoms, an aryl (heteroaryl)amino group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms It means substituted with one or more substituents selected from the group consisting of an aryloxy group of 24 and an arylthionyl group having 6 to 24 carbon atoms.
The method of claim 1,
The first light emitting layer includes at least one compound represented by Formula A or Formula B,
An organic light emitting device, characterized in that the anthracene derivative represented by the following formula (E) is used as a host in the second light emitting layer.
[Formula E]

In the above [Formula E],
The substituents R ₄₁ to R ₅₆ are the same or different, and are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted A cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, Any one selected from a cyano group, a nitro group, a halogen group,
The substituent Ar ₅ is a substituted or unsubstituted C 6 to C 50 aryl group, or a substituted or unsubstituted C 2 to C 50 heteroaryl group,
The linking group L ₁ is any one 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 of 1 to 2, and when n is 2 or more, each linking group L1 is the same as or different from each other,
'Substitution' in the 'substituted or unsubstituted' in [Formula E] is deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, C2-C24 alkenyl group, C2-C24 alkynyl group, C3-C24 cycloalkyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C7-C24 arylalkyl group, C7 to 24 alkylaryl group, C2-C24 heteroaryl group, C2-C24 heteroarylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C12-C24 diarylamino group, A diheteroarylamino group having 2 to 24 carbon atoms, an aryl (heteroaryl)amino group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, an aryloxy group having 6 to 24 carbon atoms. It means being substituted with one or more substituents selected from the group consisting of 6 to 24 arylthionyl groups.
17. The method of claim 16,
The anthracene derivative represented by Formula E is an organic light emitting device, characterized in that it is an anthracene compound represented by Formula E-1 or Formula E-2 below.
[Formula E-1]

[Formula E-2]

In the [Formula E-1] and [Formula E-2],
The substituents R ₄₁ to R _{48 and} R ₄₉ to R ₅₅ are the same or different, and each independently represent hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, or a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to any one selected from an arylsilyl group, a cyano group, a nitro group, and a halogen group,
The substituent Ar ₅ is a substituted or unsubstituted C 6 to C 50 aryl group, or a substituted or unsubstituted C 2 to C 50 heteroaryl group,
The linking group L ₁₁ is any one 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 k is an integer of 1 to 2, when k is 2 or more, each connecting group L ₁₁ is the same as or different from each other,
'Substitution' in the 'substituted or unsubstituted' in [Formula E-1] and [Formula E-2] is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro 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 cycloalkyl group having 3 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms. An arylalkyl group having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, A diarylamino group having 12 to 24 carbon atoms, a diheteroarylamino group having 2 to 24 carbon atoms, an aryl (heteroaryl)amino group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, and an arylsilyl group having 6 to 24 carbon atoms. It means being substituted with one or more substituents selected from the group consisting of an aryloxy group having 6 to 24 and an arylthionyl group having 6 to 24 carbon atoms.
17. The method of claim 16,
The anthracene derivative represented by Formula E in the second light emitting layer contains at least one deuterium.
17. The method of claim 16,
In Formula E, at least one of R ₄₁ to R ₄₈ is deuterium.
17. The method of claim 16,
In Formula E, Ar ₅ is an organic light emitting device, characterized in that it is a substituent containing at least one deuterium.
17. The method of claim 16,
At least one of R ₄₉ to R ₅₆ in Formula E is an organic light emitting device, characterized in that it is a substituent containing deuterium.
17. The method of claim 16,
Formula E is an organic light emitting device, characterized in that the degree of deuterium is 20% or more.
16. The method of claim 15,
The first dopant in the first light-emitting layer and the second dopant in the second light-emitting layer are the same or different, respectively, and at least one compound selected from [Formula D1] to [Formula D10] is used. device.
15. The method of claim 14,
The organic light emitting device may include a flat panel display device; flexible display devices; devices for flat-panel lighting, either monochromatic or white; And, Monochromatic or white flexible lighting device; Organic light emitting device, characterized in that used in any one device selected from.

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