KR102469862B1 - Novel Organic compounds and Organic light emitting diode including the same - Google Patents

Abstract

The present invention relates to a novel heterocyclic compound that can be used in an organic light emitting device and an organic light emitting device including the same, wherein [Formula A] and [Formula B] are the same as described in the detailed description of the invention.

Description

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

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

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

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

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

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

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

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

However, despite the fact that various types of compounds for use in the light emitting layer of organic light emitting devices, including the prior art, have been prepared, novel materials having high efficiency, low voltage driving and long lifespan while being applicable to organic light emitting devices are still being developed. The need for development of a compound and an organic light emitting device including the same is a situation that is continuously demanded.

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

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

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

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

[Formula A] [Formula B]

In [Formula A] and [Formula B],

Wherein R ₁ to R ₁₄ are the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, 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, Substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, cyano group, nitro group, halogen group Any one selected from;

The linking groups L ₁ and L ₂ are each the same as or different from each other, and are 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 represents an integer of 0 to 2, when each of them is 2, each of the linking groups L ₁ and L ₂ are the same as or different from each other,

Wherein R and R′ are the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted carbon atom Cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, 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. is any one selected;

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

In [Formula A] and [Formula B], 'substitution' in 'substituted or unsubstituted' is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, and a carbon number 1 to 24 Halogenated alkyl group, C1-24 alkenyl group, C1-24 alkynyl group, C3-24 cycloalkyl group, C1-24 heteroalkyl group, C6-24 aryl group, C7-24 aryl Alkyl group, C7-24 alkylaryl group, C2-24 heteroaryl group, C2-24 heteroarylalkyl group, C1-24 alkoxy group, C1-24 alkylamino group, C12-24 carbon atom group Diarylamino group, C2-24 diheteroarylamino group, C7-24 aryl (heteroaryl) amino group, C1-24 alkylsilyl group, C6-24 arylsilyl group, C6-24 aryl It means that it is substituted with one or more substituents selected from the group consisting of an oxy group and an arylthionyl group having 6 to 24 carbon atoms.

When the novel organic compound represented by Formula A or Formula B according to the present invention is used as a host material in an organic light emitting device, organic light emitting devices exhibit higher efficiency, lower voltage driving, and longer lifespan than organic light emitting devices according to the prior art. element can be provided.

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

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

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

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

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

[Formula A] [Formula B]

In [Formula A] and [Formula B],

Wherein R ₁ to R ₁₄ are the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, 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, Substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, cyano group, nitro group, halogen group Any one selected from;

The linking groups L ₁ and L ₂ are each the same as or different from each other, and are 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 represents an integer of 0 to 2, when each of them is 2, each of the linking groups L ₁ and L ₂ are the same as or different from each other,

Wherein R and R′ are the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted carbon atom Cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, 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. is any one selected;

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

In [Formula A] and [Formula B], 'substitution' in 'substituted or unsubstituted' is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, and a carbon number 1 to 24 Halogenated alkyl group, C1-24 alkenyl group, C1-24 alkynyl group, C3-24 cycloalkyl group, C1-24 heteroalkyl group, C6-24 aryl group, C7-24 aryl Alkyl group, C7-24 alkylaryl group, C2-24 heteroaryl group, C2-24 heteroarylalkyl group, C1-24 alkoxy group, C1-24 alkylamino group, C12-24 carbon atom group Diarylamino group, C2-24 diheteroarylamino group, C7-24 aryl (heteroaryl) amino group, C1-24 alkylsilyl group, C6-24 arylsilyl group, C6-24 aryl It means that it is substituted with one or more substituents selected from the group consisting of an oxy group and an arylthionyl group having 6 to 24 carbon atoms.

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

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

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

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

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

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

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

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

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

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

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

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

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

On the other hand, as a more preferred example for 'substitution' in the 'substituted or unsubstituted' in [Formula A] and [Formula B], this is a deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, a carbon number of 1 to 12 alkyl group, C1-12 halogenated alkyl group, C2-12 alkenyl group, C2-12 alkynyl group, C3-12 cycloalkyl group, C1-12 heteroalkyl group, C6-18 Aryl group, C7-20 arylalkyl group, C7-20 alkylaryl group, C2-18 heteroaryl group, C2-18 heteroarylalkyl group, C1-12 alkoxy group, C1-12 Alkylamino group, C12-18 diarylamino group, C2-18 diheteroarylamino group, C7-18 aryl (heteroaryl) amino group, C1-12 alkylsilyl group, C6-18 aryl 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 [Chemical Formula A] has a linking group L1 bonded to a specific position (see Structural Formula C below) in a substituted or unsubstituted pyrene ring, and dibenzofuran substituted or unsubstituted to the linking group L1 The technical feature is that the 1-position of the group is bonded, and in addition, the organic compound represented by [Formula B] has a linking group L2 bonded to a specific position (see structural formula C below) in the substituted or unsubstituted pyrene ring, It is technically characterized in that the 2-position of the substituted or unsubstituted dibenzofuran group is bonded to the linking group L2.

[Structural Formula C]

In [Formula A] and [Formula B] according to the present invention, the compound represented by Formula A may contain at least one deuterium, and the compound represented by Formula B may contain at least one deuterium. have.

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 present invention, when the compound represented by Formula A may contain at least one deuterium and the compound represented by Formula B may include at least one deuterium, in [Formula A] At least one R is a substituent containing deuterium, and at least one R' in [Formula B] may be a substituent containing deuterium.

In addition, as an embodiment according to the present invention, the R ₁ to R _{14 ,} R , and R′ are each the same or different and independently of each other, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted Cyclic aryl group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 15 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms group, a cyano group, and a substituent selected from 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 in [Formula B], R ₈ to 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 Formula A and Formula B may each be a single bond or any one selected from [Formula 1] to [Formula 5] below.

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

[Structural Formula 4] [Structural Formula 5]

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

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

Also, as an embodiment according to the present invention, n3 and n4 in Formula A and Formula 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. In this case, preferably, n3 and n4 in Formula A and Formula B are each 1, and R in [Formula A] is substituted or unsubstituted It is a ringed 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 [Formula A] or [Formula B] 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]

At this time, in [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,

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

In addition, as an embodiment according to the present invention, n3 and n4 in Formula A and Formula B are each 1, and at least one of R ₁ to R _{7 and} R in [Formula A] has 6 carbon atoms substituted with deuterium. to 18 aryl groups, 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 according to the present invention, n3 and n4 in Formula A and Formula B are each 1, and R in [Formula A] is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms and , 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 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 118 Formula 119 Formula 120

Formula 121 Formula 122 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 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 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

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

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

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

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

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

[Formula D1]

[Formula D2]

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

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

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

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

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

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

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

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

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

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

[Formula D3]

In the above [Formula D3],

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

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

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

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

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

[Formula D4] [Formula D5]

In [Formula D4] and [Formula D5],

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

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

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

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

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

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

[Formula D6] [Formula D7]

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

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

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

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

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

[Formula D8] [Formula D9]

[Formula D10]

In [Formula D8] to [Formula D10],

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

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

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

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

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

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

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

In Formula D9,

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

In the formula D10,

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

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

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

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

<d 1> <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>

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

[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]

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

<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 typically selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

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

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

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

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

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

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

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

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

The hole injection layer material may be used without particular limitation as long as it is commonly used in the art, 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) or the like can 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 preventing electrons injected from the electron injection layer from entering the hole transport layer through the light emitting layer to improve the lifespan and efficiency of the device, and may be formed at an appropriate portion between the light emitting layer and the hole injection layer. And, preferably, it may be formed between the light emitting layer and the hole transport layer.

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

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

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

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

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

TAZ BAlq

<Compound 201> <Compound 202> BCP

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

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

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

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

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

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

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

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

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

(Example)

Synthesis Example 1. Synthesis of Chemical 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 100 g (0.278 mol) of 1,6-dibromopyrene, 33.9 g (0.278 mol) of phenylboronic acid, tetrakistriphenylphosphine palladium (Pd[PPh ₃ ] ₄ ) 6.4 g (0.006 mol), sodium carbonate 88.3 g (0.833 mol), toluene 1400 ml and water 420 ml were added and refluxed for 9 hours. After the reaction is completed, the resulting solid is filtered and discarded after cooling to room temperature, and the filtrate is extracted with ethyl acetate and water, and the organic layer is subjected to anhydrous treatment. After anhydrous treatment and concentration under reduced pressure, the mixture was separated 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 20 g (0.076 mol) of 6-bromo-1-dibenzofuranol, 11.6 g (0.091 mol) of phenylboronic acid (D5), tetrakistriphenylphosphine palladium (Pd[ PPh ₃ ] ₄ ) 1.8 g (0.002 mol), potassium carbonate 17.9 g (0.129 mol), toluene 140 ml, ethanol 35 ml and water 65 ml were added and refluxed for 5 hours. After the reaction is completed, the mixture is cooled to room temperature, extracted with ethyl acetate and water, and the organic layer is subjected to anhydrous treatment. The organic layer was concentrated under reduced pressure and recrystallized with ethyl acetate and heptane to obtain <1-b> 15.2 g (yield: 75.4%).

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

[Scheme 3]

<1-c>

A 500 ml round bottom flask is purged with nitrogen, 15.2 g (0.058 mol) of <1-b>, 6 g (0.076 mol) of pyridine, and 150 ml of dichloromethane are added, and the temperature is cooled below 0 °C. After cooling, 18.1 g (0.064 mol) of trifluoromethane sulfonic anhydride was slowly added dropwise. After the dropwise addition, the temperature of the reaction solution was raised to room temperature and stirred until the reaction was completed. After the reaction was completed, extraction was performed with dichloromethane and water, and 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 <1-c> 20 g (0.050 mol), bispinacoldiboron 16.6 g (0.065 mol), bisdiphenylphosphinoferrocendichloropalladium 0.8 g (0.001 mol), calcium acetate 9.9 g (0.101 mol) and 200 ml of 1,4-dioxane were added and refluxed for 12 hours. After 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 <1-d> 14.8 g (yield: 78.4%).

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 were 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 Chemical Formula 34

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

[Scheme 6]

<2-a>

<2-a> (yield: 79.3%) was obtained in the same manner except that phenylboronic acid (D5) was used instead of the 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 for using 1,7-dibromodibenzofuran.

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

[Scheme 8]

<2-c>

<2-c> (yield: 72.8%) was obtained by synthesizing 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%)

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 <3-a> (72.0% yield) was obtained by synthesizing in the same manner except that 6-bromo-2-dibenzofuranol was used instead and 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 by synthesizing 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]

[Formula 52] (yield 58.0%) was obtained by synthesizing in the same manner except for using <3-c> instead of <2-c> in Synthesis Example 2-4.

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]

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

MS(MALDI-TOF): m/z 449.18[M] ⁺

Synthesis Example 5. Synthesis of Formula 136

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

[Scheme 15]

<5-a>

A 1000 ml round-bottom flask was purged with nitrogen, 50 ml (0.477 mol) of a 30 wt% aqueous solution of hydrogen peroxide, 45 g (0.454 mol) of phenol (D5), 57.6 g (0.227 mol) of iodine, and 450 ml of water were added and heated at 50 ° C for 24 hours. Stir for an hour. When the reaction is complete, an aqueous solution of sodium thiosulfate is added, stirred, and the reaction solution is extracted with ethyl acetate and water, treated with 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 were added and refluxed for 8 hours. When the reaction is complete, the mixture is cooled to room temperature, extracted with ethyl acetate and water, and the organic layer is subjected to anhydrous treatment. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain <5-b> 28.6 g (yield: 64.1%).

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

[Scheme 17]

<5-c>

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 added to a 500 ml round bottom flask and refluxed for 12 hours. When the reaction is complete, after cooling the temperature to room temperature, slowly add 200 ml of 2 N-hydrochloric acid aqueous solution, stir sufficiently, and extract with ethyl acetate and water. The organic layer was concentrated and then 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>

21 g (0.104 mol) of <5-c> and 120 ml of dichloromethane were added to a 500 ml round bottom flask, and the reaction solution was cooled below 0°C. 52 g (0.208 mol) of borontribromide was slowly added dropwise, paying attention to the temperature. After the dropwise addition, the temperature of the reaction solution was raised to room temperature and stirred until the reaction was completed. When the reaction is complete, 100 ml of water is slowly added dropwise to the reaction solution, followed by sufficient stirring. The reaction solution was extracted with dichloromethane and water, treated with anhydrous, concentrated under reduced pressure, and separated by column chromatography to obtain <5-d> 15 g (yield: 76.8%).

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

[Scheme 19]

<5-e>

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

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), bispinacoldiboron 23.8 g (0.094 mol), bisdiphenylphosphinoferrocendichloropalladium 2.5 g (0.003 mol), calcium acetate 9.5 g (0.125 mol) and 200 ml of 1,4-dioxane were added and refluxed for 12 hours. After 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 <5-f> 15 g (yield: 80.6%).

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

[Scheme 21]

[Formula 136]

[Formula 136] synthesized in the same manner except for using <5-f> instead of <2-c> in Synthesis Example 2-4 (Yield 60.3%) was obtained.

MS(MALDI-TOF) : m/z 453.21[M] ⁺

Synthesis Example 6. Synthesis of Formula 1

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

[Scheme 22]

<6-a>

<6-a> (yield: 57%) was obtained by synthesizing in the same manner, except that phenylboronic acid was used instead of phenylboronic acid (D5) used in Synthesis Example 1-2.

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

[Scheme 23]

<6-b>

<6-b> (yield: 86.8%) was obtained by synthesizing in the same manner except that <6-a> was used instead of <1-b> used in Synthesis Example 1-3.

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

[Scheme 24]

<6-c>

<6-c> (yield: 79.2%) was obtained by synthesizing in the same manner except that <6-b> was used instead of <1-c> used in Synthesis Example 1-4.

Synthesis Example 6-4. Synthesis of [Formula 1]

[Scheme 25]

[Formula 1]

[Formula 1] ( Yield 52.5%) was obtained.

MS(MALDI-TOF): m/z 444.15[M] ⁺

Synthesis Example 7. Synthesis of Formula 23

Synthesis Example 7-1. Synthesis of [Formula 23]

[Scheme 26]

[Formula 23]

[Formula 23] (yield: 53.8%) was obtained by synthesizing in the same manner except that <6-c> was used instead of <1-d> used in Synthesis Example 1-5.

MS(MALDI-TOF) : m/z 520.18[M] ⁺

Synthesis Example 8. Synthesis of Formula 41

Synthesis Example 8-1. Synthesis of [Formula 41]

[Scheme 27]

[Formula 41]

[Formula 41] (yield: 54.2%) was obtained by synthesizing in the same manner except that <2-a> was used instead of <1-a> used in Synthesis Example 1-5.

MS(MALDI-TOF) : m/z 530.25[M] ⁺

Synthesis Example 9. Synthesis of Formula 57

Synthesis Example 9-1. Synthesis of [Formula 57]

[Scheme 28]

[Formula 57]

[Formula 57] (yield: 53.5%) was obtained by synthesizing in the same manner except that <3-c> was used instead of <1-d> used in Synthesis Example 1-5.

MS(MALDI-TOF) : m/z 520.18[M] ⁺

Examples 1 to 13: Manufacturing of organic light emitting device

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 1x10 ^-7 torr, films were formed on the ITO in the order of DNTPD (700 Å) and α-NPD (300 Å). As the light emitting layer, a film (300 Å) is formed by mixing the host compound according to the present invention and the dopant (BD) (3 wt%) described below, and then [E-1] and [E-2] are formed as electron transport layers. [E-2] (10Å) as an electron injection layer, and Al (1,000Å) were formed in this order at a ratio of (1:1) to manufacture an organic light emitting device. The emission characteristics of the organic light emitting device were measured at 0.4 mA.

[DNTPD] [α-NPD] [BD]

[E-1] [E-2]

Comparative Examples 1 to 4

The organic light emitting device for the comparative example was fabricated and tested in the same manner except that the following [BH1] and [BH2] were used instead of the compound according to the present invention used as a host in the device structure of the above example, and the organic light emitting device The luminescence characteristics of were measured at 0.4 mA. The structures of [BH1] and [BH2] are as follows.

[BH1] [BH2]

host V cd/A CIEx CIEy Example 1 Formula 1 3.9 8.78 0.134 0.102 Example 2 Formula 19 3.7 9.18 0.134 0.101 Example 3 Formula 23 3.8 8.90 0.134 0.101 Example 4 Formula 34 3.6 9.33 0.133 0.102 Example 5 Formula 41 3.6 9.40 0.133 0.101 Example 6 Formula 52 3.8 9.08 0.134 0.101 Example 7 Formula 57 3.8 8.86 0.134 0.102 Example 8 Formula 131 3.9 8.92 0.133 0.101 Example 9 Formula 136 3.8 8.97 0.133 0.102 Comparative Example 1 [BH1] 4.1 8.67 0.133 0.103 Comparative Example 2 [BH2] 4.0 8.52 0.133 0.102

host LT97 CIEx CIEy Example 10 Formula 41 210 0.133 0.101 Example 11 Formula 50 181 0.134 0.101 Example 12 Formula 35 194 0.133 0.101 Example 13 Formula 136 270 0.134 0.102 Comparative Example 3 [BH1] 143 0.133 0.103 Comparative Example 4 [BH2] 148 0.133 0.102

As shown in Table 1, the organic light emitting device using the compound having a pyrene group bonded to the 1st or 2nd position of the dibenzofuran group in the light emitting layer according to the present invention is located at the 3rd or 4th position of the dibenzofuran group. It can be driven at a lower voltage than the organic light emitting devices in Comparative Examples 1 and 2, in which BH 1 or BH 2, a compound in which a pyrene group is bonded, is used in the light emitting layer, and shows excellent luminous efficiency. In Figure 2, the organic light-emitting device using the compound having a pyrene group bonded to the 1st or 2nd position of the dibenzofuran group according to the present invention in the light emitting layer has a pyrene group at the 3rd or 4th position of the dibenzofuran group. The organic light emitting device according to the present invention has high applicability by showing superior characteristics of long life compared to the organic light emitting device using the compound of Comparative Examples 3 to 4 using the combined compound BH 1 or BH 2 in the light emitting layer. Able to know.

Claims (19)

A compound represented by the following [Formula A] or [Formula B].
[Formula A] [Formula B]

In [Formula A] and [Formula B],
R ₁ to R ₁₄ are the same or different and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted Any one selected from a cycloalkyl group having 3 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, and a halogen group,
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 [Formula B] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms;
The linking groups L ₁ and L ₂ are each the same as or different from each other, and are independently single bonds or any one selected from the following [Formula 1] to [Formula 2],
[Structural Formula 1] [Structural Formula 2]

In the linking group, hydrogen or deuterium may be bonded to the carbon site of the aromatic ring;
Wherein n1 and n2 are each the same or different, and each independently represents an integer of 0 to 2, when each of them is 2, each of the linking groups L ₁ and L ₂ are the same as or different from each other,
Wherein R and R' are the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted Any one selected from a cycloalkyl group having 3 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, and a halogen group,
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 a substituted or unsubstituted aryl group having 6 to 18 carbon atoms;
wherein n3 and n4 are the same or different, and each independently represents an integer of 1 to 9, and when each of them is 2 or more, each of R and R' is the same as or different from each other;
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;
Alternatively, at least one R in [Formula A] is a substituent containing deuterium, and at least one R' in [Formula B] is a substituent containing deuterium;
In [Formula A] and [Formula B], 'substitution' in 'substituted or unsubstituted' means heavy hydrogen, a halogen group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, and a carbon atom having 3 to 24 carbon atoms. In the group consisting of a cycloalkyl group having 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, an alkylsilyl group having 1 to 24 carbon atoms, and an arylsilyl group having 6 to 24 carbon atoms It means being substituted with one or more selected substituents.
delete delete delete delete delete According to claim 1,
The linking groups L ₁ and L ₂ are each a single bond.
delete According to claim 1,
In Formula A and Formula 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 a compound characterized in that a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.
According to claim 1,
The organic compound represented by [Formula A] or [Formula B] A compound characterized in that it is a compound represented by any one of the following [Formula A-1] or [Formula B-1].
[Formula A-1] [Formula B-1]

In [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,
Substituents R and R' are substituted or unsubstituted aryl groups having 6 to 18 carbon atoms.
According to claim 1,
In Formula A and Formula B, n3 and n4 are each 1,
In [Formula A], at least one of R ₁ to R _{7 and} R is an aryl group having 6 to 18 carbon atoms substituted with deuterium,
A compound characterized in that at least one of R ₈ to R _{14 and} R' in [Formula B] is a deuterium-substituted aryl group having 6 to 18 carbon atoms.
delete According to claim 1,
[Formula 19], [Formula 20], [Formula 34], [Formula 35], [Formula 41], [Formula 45], [Formula 49], [Formula 50], [Formula 52], [ A compound characterized in that it is any one selected from the group represented by Formula 79], [Formula 144] to [Formula 237].

Formula 19 Formula 20

Formula 34 Formula 35

Formula 41 Formula 45

Formula 49 Formula 50

Formula 52 Formula 79

Formula 144

Formula 145 Formula 146 Formula 147

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 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
a first electrode;
a second electrode facing the first electrode; and
An organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains a compound of any one item selected from claims 1, 7, 9 to 11, and 13. An organic light emitting device comprising more than one species.
15. The method of claim 14,
The organic layer comprises at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer.
According to claim 15,
An organic light emitting device, characterized in that the organic layer interposed between the first electrode and the second electrode includes a light emitting layer, the light emitting layer is made of a host and a dopant, and the compound is used as a host.
17. The method of claim 16,
The dopant is an organic light emitting device, characterized in that at least one selected from the following [Formula D1] to [Formula D10] is used.
[Formula D1]

[Formula D2]

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

[Formula D3]

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

[Formula D4] [Formula D5]

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

[Formula D6] [Formula D7]

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

[Formula D8] [Formula D9]

[Formula D10]

In [Formula D8] to [Formula D10],
Wherein X is any one selected from B, P, P = O,
The Q1 to Q3 are the same as T ₁ to T ₃ in [Formula D3],
The linking group Y is any one selected from NR ₃ , CR 4 R 5 , O, S, and Se;
The substituents R3 to R5 are each the same as R61 to R70 in [Formula D3],
The R ₃ to R ₅ may each be bonded to the Q ₂ ring or the Q ₃ ring to further form an alicyclic or aromatic monocyclic or polycyclic ring,
The R ₄ and R ₅ may be linked to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,
The ring formed by the Cy1 has a nitrogen (N) atom, an aromatic carbon atom in the Q1 ring to which the nitrogen (N) atom is bonded, and an aromatic carbon atom in the Q1 ring to be bonded to the Cy1, substituted or unsubstituted carbon atoms 1 to 10 alkylene groups,
In Formula D9,
'Cy2' may be added to Cy1 to form a saturated hydrocarbon ring, and the ring formed by Cy2 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, except for carbon atoms included in Cy1,
In the formula D10,
The ring formed by the Cy3 is an aromatic carbon atom in the Q3 ring to be bonded to Cy3, an aromatic carbon atom in Q3 to be bonded to a nitrogen (N) atom, a nitrogen (N) atom, and in Cy1 to which the nitrogen (N) atom is bonded. Excluding carbon atoms, it is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,
Here, 'substitution' in the 'substituted or unsubstituted' in [Formula D1] to [Formula D10] is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a carbon number 1 -24 halogenated alkyl group, C2-24 alkenyl group, C2-24 alkynyl group, C3-24 cycloalkyl group, C1-24 heteroalkyl group, C6-24 aryl group, C7-24 Arylalkyl group having 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, and 12 carbon atoms to 24 diarylamino group, C2 to 24 diheteroarylamino group, C7 to 24 aryl (heteroaryl) amino group, C1 to 24 alkylsilyl group, C6 to 24 arylsilyl group, C6 to 24 It means that it is substituted with one or more substituents selected from the group consisting of an aryloxy group of 24 and an arylthionyl group of 6 to 24 carbon atoms.
According to claim 15,
At least one layer selected from the respective layers is an organic light emitting device, characterized in that formed by a deposition process or a solution process.
According to claim 14,
The organic light emitting diode may include a flat panel display device; flexible display devices; devices for monochromatic or white flat lighting; And, a monochromatic or white flexible lighting device; characterized in that used in any one device selected from the organic light emitting device.

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