WO2020256480A1

WO2020256480A1 - Organic light-emitting device

Info

Publication number: WO2020256480A1
Application number: PCT/KR2020/007989
Authority: WO
Inventors: 허동욱; 홍성길; 허정오; 최지영; 홍완표; 이우철; 이재구
Original assignee: 주식회사 엘지화학
Priority date: 2019-06-19
Filing date: 2020-06-19
Publication date: 2020-12-24
Also published as: CN113661584B; KR102344204B1; CN113661584A; KR20200145762A

Abstract

The present invention relates to an organic light-emitting device comprising: an anode; a cathode provided opposite the anode; and a light-emitting layer provided between the anode and the cathode, wherein the light-emitting layer includes a compound represented by chemical formula 1, and the organic light-emitting device satisfies equation 1 and comprises, between the light-emitting layer and the cathode, a first organic material layer including a compound represented by chemical formula 2.

Description

Organic light emitting element

The present application relates to an organic light emitting device.

This application claims the benefit of the filing date of the Korean Patent Application No. 10-2019-0072950 filed with the Korean Intellectual Property Office on June 19, 2019, the entire contents of which are incorporated herein.

The organic light emission phenomenon is one example of converting current into visible light by an internal process of a specific organic molecule. The principle of the organic light emission phenomenon is as follows. When an organic material layer is placed between the anode and the cathode, when a current is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and the anode, respectively. The electrons and holes injected into the organic material layer recombine to form excitons, and the excitons fall back to the ground state to emit light. An organic light-emitting device using this principle may generally be composed of an organic material layer including a cathode and an anode, and an organic material layer positioned therebetween, for example, a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.

Materials used in organic light-emitting devices are pure organic materials or complex compounds in which organic materials and metals form a complex, and depending on the purpose, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. Can be divided into Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state upon oxidation is mainly used. Meanwhile, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state upon reduction is mainly used. As the light-emitting layer material, a material having both p-type and n-type properties, that is, a material having a stable form in both oxidation and reduction states, is preferable, and a material with high luminous efficiency that converts excitons to light when formed is preferred. desirable.

In addition to the above-mentioned, it is preferable that the material used in the organic light-emitting device additionally has the following properties.

First, it is preferable that the material used in the organic light emitting device has excellent thermal stability. This is because joule heat is generated by the movement of electric charges in the organic light-emitting device. Since NPB, which is currently mainly used as a material for a hole transport layer, has a glass transition temperature of 100°C or less, it is difficult to use it in an organic light emitting diode that requires a high current.

Second, in order to obtain a high-efficiency organic light-emitting device capable of low voltage driving, holes or electrons injected into the organic light-emitting device must be smoothly transferred to the light-emitting layer, and holes and electrons injected into the light-emitting layer must not escape out of the light-emitting layer. For this, the material used in the organic light emitting device must have an appropriate band gap and HOMO or LUMO energy level. In the case of PEDOT:PSS, which is used as a hole transport material in an organic light emitting device manufactured by the current solution coating method, the LUMO energy level is lower than the LUMO energy level of the organic material used as the light emitting layer material. Is having difficulty.

In addition, materials used in organic light-emitting devices must have excellent chemical stability, charge mobility, and interfacial properties with electrodes or adjacent layers. That is, the material used in the organic light-emitting device should be less deformed by moisture or oxygen. In addition, by having an appropriate hole or electron mobility, the density of holes and electrons in the emission layer of the organic light-emitting device should be balanced to maximize the formation of excitons. In addition, for the stability of the device, the interface with the electrode including metal or metal oxide must be improved.

Therefore, in the technical field, the development of organic materials having the above requirements is required.

The present specification relates to an organic light emitting device.

The present invention is an anode; Cathode; And an emission layer provided between the anode and the cathode,

The emission layer includes a compound represented by Formula 1 below,

The organic light-emitting device further includes a first organic material layer comprising a compound represented by Formula 2 below between the emission layer and the cathode,

It provides an organic light emitting device that satisfies the following formula 1.

[Formula 1]

[Formula 2]

In Formula 1,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,

Ar3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

R1 is hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

m is an integer from 0 to 7,

When m is 2 or more, R1 is the same as or different from each other,

In Formula 2,

X1 to X3 are N or CR, and at least one of X1 to X3 is N,

R is hydrogen or deuterium, or can be combined with adjacent Ar5 or Ar6 to form a ring,

Ar5 and Ar6 not bonded to R are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L5 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

L6 is a direct bond; -O-; A substituted or unsubstituted arylene group; A divalent or trivalent substituted or unsubstituted heterocyclic group; Or a trivalent substituted or unsubstituted aryl group,

L7 is a substituted or unsubstituted arylene group; A substituted or unsubstituted heteroarylene group; A trivalent substituted or unsubstituted aryl group; Or a trivalent heterocyclic group,

a and c are each 1 or 2, a+c≤3, b is 1 or 2,

When a to c are each 2, the structures in parentheses are the same as or different from each other,

n is an integer of 1 to 3,

[Equation 1]

P _EI _- P _H > 1.0

In Formula 1, P _H refers to the dipole moment value of the compound of Formula 1, and P _EI refers to the dipole moment value of the compound of Formula 2.

An organic light-emitting device comprising the compound of Formula 1 according to the present invention in the emission layer and the compound of Formula 2 in the first organic material layer emits blue light, and the compound of Formula 2 increases the dipole moment value including CN. Therefore, it is easy to control the speed of electrons transferred from the electron transport layer to the light emitting layer. Therefore, it has characteristics of low driving voltage, high luminous efficiency and high lifespan.

1 to 7 illustrate examples of an organic light-emitting device according to an exemplary embodiment of the present specification.

[Explanation of code]

101: substrate

201: anode

301: light emitting layer

302: second light-emitting layer

303: third light-emitting layer

401: first organic material layer

402: electron injection and transport layer

403: hole blocking layer

501: cathode

601: second organic material layer

701: third organic material layer

702: fourth organic material layer

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

When a member is referred to herein as being “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

In the entire specification of the present application, the term "combination of these" included in the expression of the Makushi format refers to one or more mixtures or combinations selected from the group consisting of the components described in the expression of the Makushi format, and the component It means to include one or more selected from the group consisting of.

Hereinafter, the substituents of the present specification will be described in detail below, but are not limited thereto.

In this specification,

Means a site bonded to another substituent or a bonding portion.

In the present specification, the term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and 2 or more When substituted, two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group; Alkyl group; Cycloalkyl group; Alkoxy group; Alkenyl group; Aryloxy group; Aralkyl group; Silyl group; Phosphine oxide group; Amine group; Aryl group; And substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group, or substituted or unsubstituted with two or more substituents connected among the above-exemplified substituents.

Connection of two or more substituents among the exemplified substituents may mean a case in which the same or different substituents are successively connected, such as a heterocyclic group substituted with an aryl group substituted with an alkyl group. In addition, the connection of three substituents is not only that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, but also (substituent 2) and (substituent 3) are connected to (substituent 1). Include.

In the present specification, the alkyl group may be a straight chain, branched chain or cyclic chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3- Dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2- Propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but these Is not limited to

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the alkynyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include an alkynyl group such as ethynyl, propynyl, 2-methyl-2propynyl, 2-butynyl, and 2-pentynyl, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. Does not.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. May be, but is not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the phosphine oxide group specifically includes diphenylphosphine oxide group, dinaphthylphosphine oxide, etc., but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Monoalkylamine group; Dialkylamine group; N-alkylarylamine group; Monoarylamine group; Diarylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

When the fluorenyl group is substituted,

,

,

,

Etc. However, it is not limited thereto.

The aryl group may be substituted with an alkyl group and may function as an arylalkyl group. The alkyl group may be selected from the above examples.

In the present specification, the heteroaryl group includes one or more atoms and heteroatoms other than carbon, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a pyrimidine group, a triazine group, a triazole group, a quinolinyl group, a quinazoline group, Carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthroline group, isoxazole group, thiadiazole group, And a dibenzofuran group, but is not limited thereto.

In the present specification, an arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

In the present specification, a heteroarylene group refers to a heteroaryl group having two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heteroaryl group may be applied.

In the present specification, the meaning of "two adjacent groups are bonded to each other to form a ring" means a substituted or unsubstituted hydrocarbon ring by bonding with an adjacent group; Or it means to form a substituted or unsubstituted heterocycle.

In the present specification, the ring is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or the aryl group, except for the non-monovalent one.

In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.

In the present specification, the heterocycle includes one or more atoms and heteroatoms other than carbon, and specifically, the heterocycle may include one or more atoms selected from the group consisting of O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group except that it is not monovalent.

In one embodiment of the present specification, the first organic material layer is provided in contact with the emission layer.

In the exemplary embodiment of the present specification, the emission layer including Formula 1 is a blue emission layer.

In the exemplary embodiment of the present specification, the light-emitting layer including Formula 1 further includes a dopant.

In the exemplary embodiment of the present specification, the light emitting layer including Formula 1 further includes a dopant, and the dopant is an amine compound.

In the exemplary embodiment of the present specification, the light emitting layer including Formula 1 further includes a dopant, and the dopant is a pyrene-based amine compound.

In an exemplary embodiment of the present specification, the light emitting layer including Formula 1 includes Formula 1 and a dopant in a weight ratio of 1:1 to 99:1.

In the exemplary embodiment of the present specification, the light emitting layer including Formula 1 includes Formula 1 and a dopant in a weight ratio of 2:1 to 50:1.

In the exemplary embodiment of the present specification, the light emitting layer including Formula 1 includes Formula 1 and a dopant in a weight ratio of 25:1.

In an exemplary embodiment of the present specification, the first organic material layer includes an electron transport layer; Or an electron injection and transport layer.

In the exemplary embodiment of the present specification, the first organic material layer is an electron injection and transport layer.

In the exemplary embodiment of the present specification, the first organic material layer is an electron injection and transport layer, and further includes a metal complex.

In the exemplary embodiment of the present specification, the first organic material layer is an electron injection and transport layer, and further includes a lithium-based complex.

In the exemplary embodiment of the present specification, the first organic material layer is an electron injection and transport layer, and further includes lithium quinolate.

In the exemplary embodiment of the present specification, the first organic material layer further includes a metal complex.

In the exemplary embodiment of the present specification, the first organic material layer further includes a lithium-based complex.

In the exemplary embodiment of the present specification, the first organic material layer further includes lithium quinolate.

In the exemplary embodiment of the present specification, the first organic material layer includes the compound of Formula 2 and the metal complex in a weight ratio of 99:1 to 1:99.

In the exemplary embodiment of the present specification, the first organic material layer includes the compound of Formula 2 and the metal complex in a weight ratio of 2:1 to 1:2.

In the exemplary embodiment of the present specification, the first organic material layer includes the compound of Formula 2 and the metal complex in a weight ratio of 1: 1.

In an exemplary embodiment of the present specification, the first organic material layer includes an electron transport layer; Or an electron injection and transport layer, and includes a hole blocking layer between the first organic material layer and the emission layer.

In an exemplary embodiment of the present specification,

if a is 1 and c is 1,

b is 1 or 2, L7 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, and when b is 2, L7 is the same as or different from each other,

L6 is a direct bond; -O-; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

if a is 1 and c is 2,

b is 1, L7 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

L6 is a trivalent substituted or unsubstituted aryl group,

if a is 2 and c is 1,

b is 1, L7 is a trivalent substituted or unsubstituted aryl group; Or a trivalent heterocyclic group, and L6 is a direct bond; -O-; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with deuterium; A phenanthrene group unsubstituted or substituted with deuterium; Biphenyl group unsubstituted or substituted with deuterium; Or a terphenyl group unsubstituted or substituted with deuterium.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with deuterium; A phenanthrene group unsubstituted or substituted with deuterium; Biphenyl group; Or terphenyl group.

In the exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a heteroaryl group containing a substituted or unsubstituted O or S having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a C2-C20 heteroaryl group.

In the exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a C2-C20 heteroaryl group.

In the exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a heteroaryl group containing O or S having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar3 is an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; Or a C2-C20 heteroaryl group.

In the exemplary embodiment of the present specification, Ar3 is an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; Or a C2-C20 heteroaryl group.

In the exemplary embodiment of the present specification, Ar3 is an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; Or a heteroaryl group containing O or S having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar3 is an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; Or a heteroaryl group containing O or S having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar3 is a phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with deuterium; A phenanthrene group unsubstituted or substituted with deuterium; Biphenyl group unsubstituted or substituted with deuterium; Terphenyl group unsubstituted or substituted with deuterium; Dibenzofuran group; Or a dibenzothiophene group.

In the exemplary embodiment of the present specification, Ar3 is a phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with deuterium; A phenanthrene group unsubstituted or substituted with deuterium; Biphenyl group; Dibenzofuran group; Or a dibenzothiophene group.

In the exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or it is a naphthylene group.

In the exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; Or it is selected from the following structural formula.

In the above structural formula, the dotted line means the bonding position.

In the exemplary embodiment of the present specification, R1 is hydrogen; Or deuterium.

In the exemplary embodiment of the present specification, m is 7, R1 is the same as or different from each other, and each independently hydrogen or deuterium.

In the exemplary embodiment of the present specification, m is 7, R1 is the same as each other and is hydrogen or deuterium.

In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, when R is not combined with Ar5 or Ar6, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

When R is bonded to Ar5 or Ar6, Ar5 or Ar6 not bonded is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, when R is not bonded with Ar5 or Ar6, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 2 to C 20 heteroaryl group,

When R is bonded to Ar5 or Ar6, Ar5 or Ar6 not bonded is hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroaryl group.

In the exemplary embodiment of the present specification, when R is not bonded to Ar5 or Ar6, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C 2 to C 20 heteroaryl group,

When R is bonded to Ar5 or Ar6, Ar5 or Ar6 not bonded is hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroaryl group.

In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted pyridine group; Or a substituted or unsubstituted spirofluorenexanthene group.

In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; Pyridine group; Or a spirofluorenezanthene group.

In the exemplary embodiment of the present specification, R is Ar5 or Ar6 not bonded, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R is Ar5 or Ar6 not bonded, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R and Ar5 or Ar6 are not bonded, and Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted pyridine group; Or a substituted or unsubstituted spirofluorenexanthene group.

In the exemplary embodiment of the present specification, R and Ar5 or Ar6 are not bonded, and Ar5 and Ar6 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; Pyridine group; Or a spirofluorenezanthene group.

In the exemplary embodiment of the present specification, R and Ar5 or Ar6 are bonded, and Ar5 or Ar6 not bonded is hydrogen.

In the exemplary embodiment of the present specification, R and Ar5 may be bonded to each other to form a quinoline ring.

In an exemplary embodiment of the present specification, of Formula 1

The structure is

Can be

In an exemplary embodiment of the present specification, of Formula 1

The structure may be a phenanthroline group unsubstituted or substituted with an aryl group or a heterocyclic group.

In an exemplary embodiment of the present specification, of Formula 1

The structure may be a phenanthroline group.

In an exemplary embodiment of the present specification, of Formula 1

The structure is

Can be

In the exemplary embodiment of the present specification, a and c are 1, and L5 and L7 are the same as or different from each other, and each independently a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroarylene group.

In the exemplary embodiment of the present specification, a and c are 1, and L5 and L7 are the same as or different from each other, and each independently a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted divalent terphenyl group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent fluorenyl group; A substituted or unsubstituted divalent dibenzofuran group; A substituted or unsubstituted divalent dibenzothiophene group; Or a substituted or unsubstituted divalent spirofluoroxanthene group.

In the exemplary embodiment of the present specification, L5 is a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroarylene group.

In the exemplary embodiment of the present specification, L5 is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted divalent terphenyl group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent fluorenyl group; A substituted or unsubstituted divalent dibenzofuran group; A substituted or unsubstituted divalent dibenzothiophene group; Or a substituted or unsubstituted divalent spirofluoroxanthene group.

In the exemplary embodiment of the present specification, L5 is a direct bond; Phenylene group; Biphenylylene group; Or it is a naphthylene group.

In the exemplary embodiment of the present specification, L7 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; A substituted or unsubstituted C2 to C20 heteroarylene group; A trivalent substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a trivalent C2-C20 heterocyclic group.

In the exemplary embodiment of the present specification, a and c are 1, and L7 is a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted divalent terphenyl group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent fluorenyl group; A substituted or unsubstituted divalent dibenzofuran group; A substituted or unsubstituted divalent dibenzothiophene group; Or a substituted or unsubstituted divalent spirofluoroxanthene group.

In the exemplary embodiment of the present specification, L6 is a direct bond; -O-; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; A substituted or unsubstituted C2 to C20 heteroarylene group; Or a trivalent substituted or unsubstituted aryl group having 2 to 30 carbon atoms.

In the exemplary embodiment of the present specification, L6 is a direct bond; -O-; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted divalent terphenyl group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent fluorenyl group; A substituted or unsubstituted divalent dibenzofuran group; A substituted or unsubstituted divalent dibenzothiophene group; Or a substituted or unsubstituted divalent spirofluoroxanthene group.

In the exemplary embodiment of the present specification, L6 is a direct bond; -O-; Phenylene group; Biphenylylene group; Naphthylene group; A divalent fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Or a divalent spirofluoroxanthene group.

In the exemplary embodiment of the present specification, "substituted or unsubstituted" is an alkyl group; Aryl group; And substituted with one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted with a substituent to which two or more substituents are connected among the substituents.

In the definition of L5 to L7 in the present specification, "substituted or unsubstituted" is an alkyl group; Aryl group; And substituted with one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted with a substituent to which two or more substituents are connected among the substituents.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is selected from the following structural formula.

In an exemplary embodiment of the present specification, the compound represented by Formula 2 is selected from the following structural formula.

In the exemplary embodiment of the present specification, the emission layer further includes a compound represented by Formula 3 below.

[Formula 3]

In Chemical Formula 3,

X10 is B or P(=O),

Y1 is O, S or NRa, Y2 is O, S or NRb,

Cy1 to Cy3 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,

Ra is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with Cy1 or Cy3 to form a substituted or unsubstituted ring,

Rb is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with Cy2 or Cy3 to form a substituted or unsubstituted ring.

In the exemplary embodiment of the present specification, the compound represented by Formula 3 may be selected from the following structural formula.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

For example, the structure of an organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3.

1 illustrates a structure of an organic light emitting diode in which an anode 201, a light emitting layer 301, a first organic material layer 401, and a cathode 501 are sequentially stacked on a substrate 101.

FIG. 2 illustrates a structure of an organic light-emitting device in which an anode 201, an emission layer 301, an electron injection and transport layer 402, and a cathode 501 are sequentially stacked on a substrate 101.

3 illustrates a structure of an organic light emitting diode in which an anode 201, a light emitting layer 301, a hole blocking layer 403, an electron injection and transport layer 402, and a cathode 501 are sequentially stacked on a substrate 101. have.

1 to 3 illustrate an organic light emitting device and are not limited thereto.

In the exemplary embodiment of the present specification, at least one additional light emitting layer may be further included between the anode and the cathode.

In the exemplary embodiment of the present specification, at least one additional emission layer may be further included between the anode and the cathode, and the maximum emission wavelengths of the emission layer and at least one additional emission layer are different from each other.

In the exemplary embodiment of the present specification, the light-emitting layer and at least one additional light-emitting layer are positioned side by side between the anode and the cathode. Positioning side by side means that the positions of the two light emitting layers are the same distance from the anode or the cathode, meaning that they are positioned side by side on the same position.

In the exemplary embodiment of the present specification, the light-emitting layer and the at least one additional light-emitting layer are arranged in a vertical or horizontal direction on a surface facing the anode and the cathode.

In the exemplary embodiment of the present specification, one of the light-emitting layer and one or more additional light-emitting layers includes a fluorescent dopant, and any one of the other light-emitting layers includes a phosphorescent dopant.

In the exemplary embodiment of the present specification, of the emission layer and the at least one additional emission layer, the emission layer includes a fluorescent dopant, and the at least one additional emission layer includes a phosphorescent dopant.

In the exemplary embodiment of the present specification, a second emission layer may be further included between the anode and the cathode.

In the exemplary embodiment of the present specification, a second emission layer is further included between the anode and the cathode, and the emission layer and the second emission layer have different wavelength bands.

In the exemplary embodiment of the present specification, a second emission layer is further included between the anode and the cathode, and maximum emission wavelengths of the emission layer and the second emission layer are different.

In the exemplary embodiment of the present specification, a second emission layer is further included between the anode and the cathode, one of the emission layer and the second emission layer includes a fluorescent dopant, and the other emission layer includes a phosphorescent dopant.

In the exemplary embodiment of the present specification, a second emission layer is further included between the anode and the cathode, the emission layer includes a phosphorescent dopant, and the second emission layer includes a fluorescent dopant.

In the exemplary embodiment of the present specification, a second emission layer is further included between the anode and the cathode, the emission layer includes a fluorescent dopant, and the second emission layer includes a phosphorescent dopant.

In the exemplary embodiment of the present specification, a second emission layer may be further included between the anode and the cathode, and the emission layer and the second emission layer may be positioned side by side.

In the exemplary embodiment of the present specification, a second emission layer is further included between the anode and the cathode, the emission layer and the second emission layer may be positioned side by side, and the emission layer and the second emission layer have different wavelength bands.

In the exemplary embodiment of the present specification, a second emission layer is further included between the anode and the cathode, the emission layer and the second emission layer may be positioned side by side, and the maximum emission wavelengths of the emission layer and the second emission layer are different from each other. .

In the exemplary embodiment of the present specification, a second emission layer is further included between the anode and the cathode, and the emission layer and the second emission layer may be arranged in a vertical or horizontal direction on a surface opposite to the anode and the cathode.

In the exemplary embodiment of the present specification, a second emission layer is further included between the anode and the cathode, and the emission layer and the second emission layer may be arranged in a vertical or horizontal direction on a surface opposite to the anode and the cathode, and the The light emitting layer and the second light emitting layer have different wavelength bands.

In the exemplary embodiment of the present specification, a second emission layer is further included between the anode and the cathode, and the emission layer and the second emission layer may be arranged in a vertical or horizontal direction on a surface opposite to the anode and the cathode, and the The maximum emission wavelengths of the emission layer and the second emission layer are different from each other.

In the exemplary embodiment of the present specification, a second emission layer 302 is further included between the anode 201 and the cathode 501, and the emission layer and the second emission layer are horizontally opposite to the anode and the cathode. The structure of the organic light emitting device in this case may be shown in FIG. 4, and a second organic material layer 601 may be further included between the light emitting layer of FIG. 4 and the second light emitting layer.

In the exemplary embodiment of the present specification, the second organic material layer in FIG. 4 is a hole transport layer. It includes a hole injection layer, or a layer that simultaneously transports and injects holes.

In the exemplary embodiment of the present specification, the compound of Formula 1 may be included in the emission layer 301 in FIG. 4, and the compound of Formula 1 may be included in the second emission layer 302.

In the exemplary embodiment of the present specification, the compound of Formula 1 is included in the emission layer 301 and the second emission layer 302 in FIG. 4.

In the exemplary embodiment of the present specification, a second emission layer 302 is further included between the anode 201 and the cathode 501, and the second emission layer is arranged horizontally on a surface opposite to the anode and the cathode. In this case, the second emission layer 302 may be arranged between the emission layer 301 and the anode 201, and a second organic material layer 601 may be provided between the anode and the second emission layer. A third organic material layer 701 may be provided between the emission layer and the second emission layer.

The structure is illustrated in FIG. 5. The structure of FIG. 5 is an anode 201, a second organic material layer 601, a second light-emitting layer 302, a third organic material layer 701, a light-emitting layer 301, a first organic material layer 401, and a cathode on the substrate 101. 501 is an organic light-emitting device in which 501 is sequentially stacked.

In the exemplary embodiment of the present specification, a second emission layer 302 is further included between the anode 201 and the cathode 501, and the second emission layer is arranged horizontally on a surface opposite to the anode and the cathode. I can. In this case, the second emission layer may be arranged between the emission layer and the first organic material layer. A second organic material layer may be provided between the anode and the emission layer, and a third organic material layer 701 may be provided between the second emission layer and the first organic material layer. The structure is illustrated in FIG. 6.

In the exemplary embodiment of the present specification, at least one additional emission layer may be further included between the emission layer and the cathode.

In the exemplary embodiment of the present specification, at least one emission layer may be further included between the emission layer and the first organic material layer.

In the exemplary embodiment of the present specification, at least one additional light emitting layer may be further included between the light emitting layer and the anode.

In the exemplary embodiment of the present specification, when at least one additional light emitting layer is further included between the light emitting layer and the anode, the wavelength bands of each light emitting layer are different from each other.

In the exemplary embodiment of the present specification, when one or more additional emission layers are further included between the emission layer and the anode, the maximum emission wavelengths of each emission layer are different from each other.

In the exemplary embodiment of the present specification, when one or more additional light-emitting layers are further included between the light-emitting layer and the anode, at least one light-emitting layer includes a fluorescent dopant, and the other one or more light-emitting layers includes a phosphorescent dopant.

In the exemplary embodiment of the present specification, 1 to 3 emission layers may be further included between the emission layer and the anode.

In the exemplary embodiment of the present specification, a second emission layer may be further included between the emission layer and the anode.

In the exemplary embodiment of the present specification, a second emission layer may be further included between the emission layer and the anode, and a second organic material layer may be further included between the emission layer and the second emission layer.

In the exemplary embodiment of the present specification, a second emission layer may be further included between the emission layer and the anode, a second organic material layer is further included between the emission layer and the second emission layer, and the emission layer and the second emission layer are different from each other. Have a wavelength band

In the exemplary embodiment of the present specification, a second emission layer may be further included between the emission layer and the anode, a second organic material layer is further included between the emission layer and the second emission layer, and maximum light emission of the emission layer and the second emission layer The wavelengths are different from each other.

In the exemplary embodiment of the present specification, a second emission layer may be further included between the emission layer and the anode, a second organic material layer is further included between the emission layer and the second emission layer, and the emission layer includes a phosphorescent dopant. , The second emission layer includes a fluorescent dopant.

In the exemplary embodiment of the present specification, a second emission layer may be further included between the emission layer and the anode, a second organic material layer is further included between the emission layer and the second emission layer, and the emission layer includes a fluorescent dopant, The second light-emitting layer includes a phosphorescent dopant.

In the exemplary embodiment of the present specification, a second emission layer may be further included between the emission layer and the anode, and a third emission layer may be further included between the second emission layer and the anode.

In one embodiment of the present specification, further comprising a second emission layer between the emission layer and the anode, further comprising a third emission layer between the second emission layer and the anode, wherein the emission layer, the second emission layer, and the third emission layer are They have different wavelength bands.

In the exemplary embodiment of the present specification, further comprising a second emission layer between the emission layer and the anode, further comprising a third emission layer between the second emission layer and the anode, wherein the emission layer, the second emission layer, the third emission layer The maximum emission wavelengths are different from each other.

In the exemplary embodiment of the present specification, further comprising a second emission layer between the emission layer and the anode, further comprising a third emission layer between the second emission layer and the anode, the emission layer, the second emission layer, the third emission layer One contains a phosphorescent dopant and the other contains a fluorescent dopant.

In the exemplary embodiment of the present specification, further comprising a second emission layer between the emission layer and the anode, further comprising a third emission layer between the second emission layer and the anode, the emission layer, the second emission layer, the third emission layer One contains a fluorescent dopant and the other contains a phosphorescent dopant.

In one embodiment of the present specification, further comprising a second emission layer between the emission layer and the anode, further comprising a third emission layer between the second emission layer and the anode, wherein the emission layer, the second emission layer, and the third emission layer are All contain fluorescent dopants.

In one embodiment of the present specification, further comprising a second emission layer between the emission layer and the anode, further comprising a third emission layer between the second emission layer and the anode, wherein the emission layer, the second emission layer, and the third emission layer are It is a blue fluorescent light emitting layer.

In the exemplary embodiment of the present specification, further comprising a second emission layer between the emission layer and the anode, further comprising a third emission layer between the second emission layer and the anode, between the emission layer, the second emission layer, and the third emission layer One or more organic material layers may be further included in

In the exemplary embodiment of the present specification, a second emission layer is further included between the emission layer and the anode, and a third emission layer is further included between the second emission layer and the anode.

In addition, one or more organic material layers may be further included between the emission layer and the second emission layer, between the second emission layer and the third emission layer, and between the third emission layer and the anode.

The structure is illustrated in FIG. 7, and on the substrate 101, the anode 201, the second organic material layer 601, the third light emitting layer 303, the fourth organic material layer 702, the second light emitting layer 302, 3 An organic light-emitting device in which an organic material layer 701, an emission layer 301, a first organic material layer 401, and a cathode 501 are sequentially stacked.

In the exemplary embodiment of the present specification, the organic light emitting device is a light emitting layer, a hole injection layer, and a hole transport layer. It further includes one or two or more layers selected from the group consisting of an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

In the exemplary embodiment of the present specification, the organic light emitting device further includes a hole transport layer, and may include two or more types of hole transport materials. In the exemplary embodiment of the present specification, the organic light emitting device may further include a hole transport layer, and may be formed by sequentially depositing different hole transport materials.

In the exemplary embodiment of the present specification, the organic light-emitting device further includes a two-layer hole transport layer, and the two-layer hole transport layer includes different hole transport materials.

In the exemplary embodiment of the present specification, the organic light-emitting device further includes two hole transport layers, and the two hole transport layers include amine compounds different from each other. In another exemplary embodiment, the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes a composition including the compound.

For example, the organic light emitting device of the present specification may be manufactured by sequentially laminating an anode, a light emitting layer, a first organic material layer, and a cathode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, an anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate. And, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be produced by depositing a material that can be used as a cathode thereon. In addition to such a method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In the exemplary embodiment of the present specification, the organic material layer including the material is formed using spin coating.

In another exemplary embodiment, the organic material layer containing the composition is formed by a printing method.

In the state of the present specification, the printing method includes, for example, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing, but is not limited thereto.

As the anode material, a material having a large work function is preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO:Al or SnO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

The cathode material is generally preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and is generated from the light emitting layer. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer.The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer such as poly(3,4-ethylene dioxythiophene)-polystyrene sulfonate, and a block copolymer having a conjugated portion and a non-conjugated portion, but are limited thereto. It is not.

The light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

In addition to the material of Formula 1, the emission layer may include an additional host material and a dopant material. In addition, not only the emission layer, but also one or more additional emission layers, the second emission layer, and the third emission layer may include the compound of Formula 1 or other host materials and topants. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. In addition, a polymer compound may be used, and a polymer compound such as poly-1,4-phenylene or polyfluorene may be used, but is not limited thereto.

Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compound is substituted or unsubstituted A compound in which at least one arylvinyl group is substituted on the arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer.As an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Do. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, has an excellent electron injection effect on the light emitting layer or light emitting material, and injects holes of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

The first organic material layer may be composed of a compound of Formula 2, and may further include the aforementioned hole transport material or a hole injection material in addition to the compound of Formula 2.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

The hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but are not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

Hereinafter, examples will be described in detail in order to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.

제조예Manufacturing example 1: 화합물 H1의 제조 1: Preparation of compound H1

After completely dissolving the compound H1-A (10 g, 24.4 mmol) and the compound H1-B (4.2 g, 24.4 mmol) in tetrahydrofuran (100 mL), potassium carbonate (10.1 g, 73.3 mmol) was added to 50 dissolved in mL and added. After tetrakistriphenyl-phosphinopalladium (0.84g, 0.733 mmol) was added, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed twice with tetrahydrofuran and ethyl acetate, respectively, to prepare compound H1 (8.9 g, yield 80%).

MS [M+H] ⁺ = 457

제조예Manufacturing example 2: 화합물 H2의 제조 2: Preparation of compound H2

A compound represented by Chemical Formula H2 was prepared in the same manner as the method for preparing H1 in Preparation Example 1, except that each starting material was used as in the above reaction formula.

MS [M+H] ⁺ = 507

제조예Manufacturing example 3: 화합물 H3의 제조 3: Preparation of compound H3

A compound represented by Chemical Formula H3 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction formula.

MS [M+H] ⁺ = 507

제조예Manufacturing example 4: 화합물 H4의 제조 4: Preparation of compound H4

A compound represented by Chemical Formula H4 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.

MS [M+H] ⁺ = 557

제조예Manufacturing example 5: 화합물 H5의 제조 5: Preparation of compound H5

A compound represented by Chemical Formula H5 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction formula.

MS [M+H] ⁺ = 578

제조예Manufacturing example 6: 화합물 H6의 제조 6: Preparation of compound H6

A compound represented by Chemical Formula H6 was prepared in the same manner as the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction formula.

MS [M+H] ⁺ = 571

제조예Manufacturing example 7: 화합물 H7의 제조 7: Preparation of compound H7

A compound represented by Chemical Formula H7 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.

MS [M+H] ⁺ = 547

제조예Manufacturing example 8: 화합물 E1의 제조 8: Preparation of compound E1

A compound represented by Formula E1 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction formula.

MS [M+H] ⁺ = 563

제조예Manufacturing example 9: 화합물 E2의 제조 9: Preparation of compound E2

A compound represented by Formula E2 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction formula.

MS [M+H] ⁺ = 613

제조예Manufacturing example 10: 화합물 E3의 제조 10: Preparation of compound E3

A compound represented by Formula E3 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.

MS [M+H] ⁺ = 537

제조예Manufacturing example 11: 화합물 E4의 제조 11: Preparation of compound E4

A compound represented by Formula E4 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.

MS [M+H] ⁺ = 613

제조예Manufacturing example 12: 화합물 E5의 제조 12: Preparation of compound E5

A compound represented by Formula E5 was prepared in the same manner as the method for preparing H1 of Preparation Example 1, except that each starting material was used as in the above reaction formula.

MS [M+H] ⁺ = 714

제조예Manufacturing example 13: 화합물 E6의 제조 13: Preparation of compound E6

A compound represented by Formula E6 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.

MS [M+H] ⁺ = 613

제조예Manufacturing example 14: 화합물 E7의 제조 14: Preparation of compound E7

A compound represented by Formula E7 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction formula.

MS [M+H] ⁺ = 663

제조예Manufacturing example 15: 화합물 E8의 제조 15: Preparation of compound E8

A compound represented by Formula E8 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction formula.

MS [M+H] ⁺ = 613

제조예Manufacturing example 16: 화합물 E9의 제조 16: Preparation of compound E9

A compound represented by Formula E9 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.

MS [M+H] ⁺ = 665

제조예Manufacturing example 17: 화합물 E10의 제조 17: Preparation of compound E10

A compound represented by Formula E10 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.

MS [M+H] ⁺ = 741

제조예Manufacturing example 18: 화합물 E11의 제조 18: Preparation of compound E11

A compound represented by Formula E11 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.

MS [M+H] ⁺ = 665

제조예Manufacturing example 19: 화합물 E12의 제조 19: Preparation of compound E12

A compound represented by Formula E12 was prepared in the same manner as in the method for preparing H1 in Preparation Example 1, except that each starting material was used in the above reaction formula.

MS [M+H] ⁺ = 665

제조예Manufacturing example 20: 화합물 E13의 제조 20: Preparation of compound E13

A compound represented by Formula E13 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.

MS [M+H] ⁺ = 665

제조예Manufacturing example 21: 화합물 E14의 제조 21: Preparation of compound E14

A compound represented by Formula E14 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction formula.

MS [M+H] ⁺ = 727

제조예Manufacturing example 22: 화합물 E15의 제조 22: Preparation of compound E15

A compound represented by Formula E15 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction formula.

MS [M+H] ⁺ = 642

제조예Manufacturing example 23: 화합물 E16의 제조 23: Preparation of compound E16

A compound represented by Formula E16 was prepared in the same manner as in the method for preparing H1 in Preparation Example 1, except that each starting material was used in the above reaction scheme.

MS [M+H] ⁺ = 744

제조예Manufacturing example 24: 화합물 E17의 제조 24: Preparation of compound E17

A compound represented by Formula E17 was prepared in the same manner as in the method for preparing H1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.

MS [M+H] ⁺ = 688

<< 실험예Experimental example 1> 1>

Example 1

A glass substrate coated with a thin film of 1000 Å of ITO (indium tin oxide) was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered by a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

The following HI-A compound was thermally vacuum deposited to a thickness of 600 Å on the prepared ITO transparent electrode to form a hole injection layer. On the hole injection layer, 50 Å of the following HAT compound and 60 Å of the following HT-A compound were sequentially vacuum-deposited to form a hole transport layer.

Subsequently, the H1 compound and the following BD compound with a film thickness of 200 Å were vacuum-deposited at a weight ratio of 25:1 on the hole transport layer to form a light emitting layer.

Compound E1 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 on the emission layer to form an electron injection and transport layer with a thickness of 350Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer.

Was maintained at the deposition rate of the organic material in the above process, 0.4 to 0.9 Å / sec, the lithium fluoride of the cathode was 0.3 Å / sec, the aluminum is 2 Å / sec was maintained at a deposition rate of, During the deposition, a vacuum 1Х10 ^-7 To 5Х10 ^-5 torr was maintained, an organic light emitting device was manufactured.

실시예Example 2 내지 101 및 2 to 101 and 비교예Comparative example 1 내지 121 1 to 121

Instead of H1 of the light emitting layer of Example 1 and E1 of the electron injection and transport layer, an organic light emitting device was manufactured in the same manner using the compounds described in the compounds of Table 1 below.

For the organic light emitting devices of Examples 1 to 101 and Comparative Examples 1 to 121, the driving voltage and luminous efficiency were measured at a current density of 10 mA/cm ² , and 90% of the initial luminance at a current density of 20 mA/cm ² The time to become (T90) was measured. The results are shown in Table 1 below.

구분(화합물)Classification (compound)			전압(V@10 mA/cm²)Voltage (V@10 mA/cm ² )	효율(cd/A@10 mA/cm²)Efficiency (cd/A@10 mA/cm ² )	색좌표(x, y)Color coordinates (x, y)	수명(h)(T90 at 20 mA/cm²)Life (h)(T90 at 20 mA/cm ² )
실시예 1 Example 1	H1H1	E1E1	4.354.35	6.006.00	(0.135, 0.089)(0.135, 0.089)	401401
실시예 2Example 2	H1H1	E2E2	4.304.30	6.136.13	(0.135, 0.087)(0.135, 0.087)	374374
실시예 3Example 3	H1H1	E3E3	4.334.33	6.036.03	(0.135, 0.088)(0.135, 0.088)	390390
실시예 4Example 4	H1H1	E4E4	4.294.29	6.306.30	(0.133, 0.088)(0.133, 0.088)	311311
실시예 5Example 5	H1H1	E5E5	4.504.50	5.805.80	(0.133, 0.088)(0.133, 0.088)	593593
실시예 6Example 6	H1H1	E6E6	4.314.31	6.116.11	(0.133, 0.088)(0.133, 0.088)	376376
실시예 7Example 7	H1H1	E7E7	4.264.26	6.316.31	(0.135, 0.089)(0.135, 0.089)	310310
실시예 8Example 8	H1H1	E8E8	4.284.28	6.306.30	(0.135, 0.087)(0.135, 0.087)	308308
실시예 9Example 9	H1H1	E9E9	4.334.33	6.126.12	(0.135, 0.088)(0.135, 0.088)	380380
실시예 10Example 10	H1H1	E10E10	4.314.31	6.156.15	(0.133, 0.088)(0.133, 0.088)	344344
실시예 11Example 11	H1H1	E11E11	4.204.20	6.196.19	(0.133, 0.088)(0.133, 0.088)	368368
실시예 12Example 12	H1H1	E12E12	4.384.38	6.026.02	(0.133, 0.088)(0.133, 0.088)	399399
실시예 13Example 13	H1H1	E13E13	4.274.27	6.296.29	(0.135, 0.089)(0.135, 0.089)	320320
실시예 14Example 14	H1H1	E14E14	4.264.26	6.276.27	(0.135, 0.087)(0.135, 0.087)	335335
실시예 15Example 15	H2H2	E1E1	4.304.30	6.046.04	(0.135, 0.088)(0.135, 0.088)	390390
실시예 16Example 16	H2H2	E2E2	4.254.25	6.176.17	(0.133, 0.088)(0.133, 0.088)	354354
실시예 17Example 17	H2H2	E3E3	4.274.27	6.076.07	(0.133, 0.088)(0.133, 0.088)	380380
실시예 18Example 18	H2H2	E4E4	4.244.24	6.346.34	(0.133, 0.088)(0.133, 0.088)	300300
실시예 19Example 19	H2H2	E5E5	4.474.47	5.845.84	(0.135, 0.089)(0.135, 0.089)	484484
실시예 20Example 20	H2H2	E6E6	4.284.28	6.156.15	(0.135, 0.087)(0.135, 0.087)	366366
실시예 21Example 21	H2H2	E7E7	4.214.21	6.356.35	(0.135, 0.088)(0.135, 0.088)	300300
실시예 22Example 22	H2H2	E8E8	4.234.23	6.336.33	(0.133, 0.088)(0.133, 0.088)	298298
실시예 23Example 23	H2H2	E9E9	4.304.30	6.146.14	(0.133, 0.088)(0.133, 0.088)	368368
실시예 24Example 24	H2H2	E10E10	4.294.29	6.166.16	(0.133, 0.088)(0.133, 0.088)	334334
실시예 25Example 25	H2H2	E11E11	4.184.18	6.236.23	(0.135, 0.089)(0.135, 0.089)	328328
실시예 26Example 26	H2H2	E12E12	4.334.33	6.056.05	(0.135, 0.087)(0.135, 0.087)	359359
실시예 27Example 27	H2H2	E13E13	4.224.22	6.326.32	(0.135, 0.088)(0.135, 0.088)	300300
실시예 28Example 28	H2H2	E14E14	4.214.21	6.296.29	(0.133, 0.088)(0.133, 0.088)	315315
실시예 29Example 29	H3H3	E1E1	4.254.25	5.995.99	(0.133, 0.088)(0.133, 0.088)	351351
실시예 30Example 30	H3H3	E2E2	4.104.10	6.126.12	(0.133, 0.088)(0.133, 0.088)	324324
실시예 31Example 31	H3H3	E3E3	4.234.23	6.016.01	(0.135, 0.089)(0.135, 0.089)	340340
실시예 32Example 32	H3H3	E4E4	4.194.19	6.276.27	(0.135, 0.087)(0.135, 0.087)	281281
실시예 33Example 33	H3H3	E5E5	4.404.40	5.775.77	(0.135, 0.088)(0.135, 0.088)	493493
실시예 34Example 34	H3H3	E6E6	4.214.21	6.066.06	(0.133, 0.088)(0.133, 0.088)	366366
실시예 35Example 35	H3H3	E7E7	4.164.16	6.286.28	(0.133, 0.088)(0.133, 0.088)	290290
실시예 36Example 36	H3H3	E8E8	4.184.18	6.276.27	(0.133, 0.088)(0.133, 0.088)	300300
실시예 37Example 37	H3H3	E9E9	4.234.23	6.106.10	(0.135, 0.089)(0.135, 0.089)	360360
실시예 38Example 38	H3H3	E10E10	4.254.25	6.146.14	(0.135, 0.087)(0.135, 0.087)	324324
실시예 39Example 39	H3H3	E11E11	4.144.14	6.206.20	(0.135, 0.088)(0.135, 0.088)	338338
실시예 40Example 40	H3H3	E12E12	4.184.18	6.056.05	(0.133, 0.088)(0.133, 0.088)	369369
실시예 41Example 41	H3H3	E13E13	4.184.18	6.246.24	(0.133, 0.088)(0.133, 0.088)	300300
실시예 42Example 42	H3H3	E14E14	4.194.19	6.306.30	(0.133, 0.088)(0.133, 0.088)	315315
실시예 43Example 43	H4H4	E1E1	4.204.20	6.006.00	(0.135, 0.089)(0.135, 0.089)	344344
실시예 44Example 44	H4H4	E2E2	4.114.11	6.116.11	(0.135, 0.087)(0.135, 0.087)	320320
실시예 45Example 45	H4H4	E3E3	4.204.20	6.026.02	(0.135, 0.088)(0.135, 0.088)	329329
실시예 46Example 46	H4H4	E4E4	4.174.17	6.306.30	(0.133, 0.088)(0.133, 0.088)	285285
실시예 47Example 47	H4H4	E5E5	4.414.41	5.795.79	(0.133, 0.088)(0.133, 0.088)	500500
실시예 48Example 48	H4H4	E6E6	4.204.20	6.056.05	(0.133, 0.088)(0.133, 0.088)	361361
실시예 49Example 49	H4H4	E7E7	4.154.15	6.246.24	(0.135, 0.089)(0.135, 0.089)	292292
실시예 50Example 50	H4H4	E8E8	4.164.16	6.266.26	(0.135, 0.089)(0.135, 0.089)	301301
실시예 51Example 51	H4H4	E9E9	4.204.20	6.116.11	(0.135, 0.087)(0.135, 0.087)	357357
실시예 52Example 52	H4H4	E10E10	4.234.23	6.126.12	(0.135, 0.088)(0.135, 0.088)	315315
실시예 53Example 53	H4H4	E11E11	4.154.15	6.216.21	(0.133, 0.088)(0.133, 0.088)	328328
실시예 54Example 54	H4H4	E12E12	4.164.16	6.046.04	(0.133, 0.088)(0.133, 0.088)	355355
실시예 55Example 55	H4H4	E13E13	4.174.17	6.226.22	(0.133, 0.088)(0.133, 0.088)	301301
실시예 56Example 56	H4H4	E14E14	4.164.16	6.316.31	(0.135, 0.089)(0.135, 0.089)	300300
실시예 57Example 57	H5H5	E1E1	4.204.20	6.016.01	(0.135, 0.087)(0.135, 0.087)	364364
실시예 58Example 58	H5H5	E2E2	4.114.11	6.106.10	(0.135, 0.088)(0.135, 0.088)	340340
실시예 59Example 59	H5H5	E3E3	4.204.20	6.036.03	(0.133, 0.088)(0.133, 0.088)	339339
실시예 60Example 60	H5H5	E4E4	4.174.17	6.316.31	(0.133, 0.088)(0.133, 0.088)	295295
실시예 61Example 61	H5H5	E5E5	4.414.41	5.785.78	(0.133, 0.088)(0.133, 0.088)	520520
실시예 62Example 62	H5H5	E6E6	4.204.20	6.046.04	(0.135, 0.089)(0.135, 0.089)	381381
실시예 63Example 63	H5H5	E7E7	4.154.15	6.236.23	(0.135, 0.087)(0.135, 0.087)	312312
실시예 64Example 64	H5H5	E8E8	4.164.16	6.256.25	(0.135, 0.088)(0.135, 0.088)	311311
실시예 65Example 65	H5H5	E9E9	4.204.20	6.106.10	(0.133, 0.088)(0.133, 0.088)	377377
실시예 66Example 66	H5H5	E10E10	4.234.23	6.116.11	(0.133, 0.088)(0.133, 0.088)	335335
실시예 67Example 67	H5H5	E11E11	4.154.15	6.206.20	(0.133, 0.088)(0.133, 0.088)	344344
실시예 68Example 68	H5H5	E12E12	4.164.16	6.036.03	(0.135, 0.089)(0.135, 0.089)	370370
실시예 69Example 69	H5H5	E13E13	4.174.17	6.216.21	(0.135, 0.088)(0.135, 0.088)	323323
실시예 70Example 70	H5H5	E14E14	4.164.16	6.316.31	(0.133, 0.088)(0.133, 0.088)	310310
실시예 71Example 71	H6H6	E1E1	4.214.21	6.026.02	(0.133, 0.088)(0.133, 0.088)	360360
실시예 72Example 72	H6H6	E2E2	4.124.12	6.116.11	(0.133, 0.088)(0.133, 0.088)	342342
실시예 73Example 73	H6H6	E3E3	4.214.21	6.016.01	(0.135, 0.089)(0.135, 0.089)	333333
실시예 74Example 74	H6H6	E4E4	4.184.18	6.306.30	(0.135, 0.089)(0.135, 0.089)	296296
실시예 75Example 75	H6H6	E5E5	4.404.40	5.775.77	(0.135, 0.087)(0.135, 0.087)	524524
실시예 76Example 76	H6H6	E6E6	4.214.21	6.056.05	(0.135, 0.088)(0.135, 0.088)	377377
실시예 77Example 77	H6H6	E7E7	4.144.14	6.226.22	(0.133, 0.088)(0.133, 0.088)	310310
실시예 78Example 78	H6H6	E8E8	4.174.17	6.246.24	(0.133, 0.088)(0.133, 0.088)	308308
실시예 79Example 79	H6H6	E9E9	4.204.20	6.116.11	(0.133, 0.088)(0.133, 0.088)	370370
실시예 80Example 80	H6H6	E10E10	4.244.24	6.106.10	(0.135, 0.089)(0.135, 0.089)	330330
실시예 81Example 81	H6H6	E11E11	4.134.13	6.216.21	(0.135, 0.087)(0.135, 0.087)	341341
실시예 82Example 82	H6H6	E12E12	4.164.16	6.046.04	(0.135, 0.088)(0.135, 0.088)	368368
실시예 83Example 83	H6H6	E13E13	4.164.16	6.216.21	(0.133, 0.088)(0.133, 0.088)	320320
실시예 84Example 84	H6H6	E14E14	4.164.16	6.316.31	(0.133, 0.088)(0.133, 0.088)	306306
실시예 85Example 85	H7H7	E1E1	4.054.05	5.805.80	(0.133, 0.088)(0.133, 0.088)	370370
실시예 86Example 86	H7H7	E2E2	4.004.00	6.036.03	(0.135, 0.089)(0.135, 0.089)	354354
실시예 87Example 87	H7H7	E3E3	4.034.03	5.945.94	(0.135, 0.087)(0.135, 0.087)	360360
실시예 88Example 88	H7H7	E4E4	4.094.09	6.116.11	(0.135, 0.088)(0.135, 0.088)	281281
실시예 89Example 89	H7H7	E5E5	4.204.20	5.675.67	(0.133, 0.088)(0.133, 0.088)	423423
실시예 90Example 90	H7H7	E6E6	4.114.11	6.016.01	(0.133, 0.088)(0.133, 0.088)	326326
실시예 91Example 91	H7H7	E7E7	4.064.06	6.116.11	(0.133, 0.088)(0.133, 0.088)	280280
실시예 92Example 92	H7H7	E8E8	4.084.08	6.106.10	(0.135, 0.089)(0.135, 0.089)	278278
실시예 93Example 93	H7H7	E9E9	4.054.05	5.925.92	(0.135, 0.088)(0.135, 0.088)	350350
실시예 94Example 94	H7H7	E10E10	4.044.04	5.955.95	(0.133, 0.088)(0.133, 0.088)	313313
실시예 95Example 95	H7H7	E11E11	4.114.11	5.995.99	(0.133, 0.088)(0.133, 0.088)	342342
실시예 96Example 96	H7H7	E12E12	4.104.10	5.825.82	(0.133, 0.088)(0.133, 0.088)	347347
실시예 97Example 97	H7H7	E13E13	4.084.08	6.006.00	(0.135, 0.089)(0.135, 0.089)	291291
실시예 98Example 98	H7H7	E14E14	4.074.07	6.076.07	(0.135, 0.089)(0.135, 0.089)	285285
실시예 99Example 99	H7H7	E15E15	4.154.15	5.785.78	(0.133, 0.088)(0.133, 0.088)	400400
실시예 100Example 100	H7H7	E16E16	4.054.05	6.086.08	(0.135, 0.089)(0.135, 0.089)	344344
실시예 101Example 101	H7H7	E17E17	4.204.20	5.585.58	(0.135, 0.087)(0.135, 0.087)	267267
비교예 1Comparative Example 1	BH-ABH-A	E1E1	4.554.55	4.004.00	(0.135, 0.087)(0.135, 0.087)	280280
비교예 2Comparative Example 2	BH-ABH-A	E2E2	4.504.50	4.114.11	(0.135, 0.088)(0.135, 0.088)	284284
비교예 3Comparative Example 3	BH-ABH-A	E3E3	4.434.43	4.004.00	(0.133, 0.088)(0.133, 0.088)	250250
비교예 4Comparative Example 4	BH-ABH-A	E4E4	4.494.49	4.214.21	(0.133, 0.088)(0.133, 0.088)	191191
비교예 5Comparative Example 5	BH-ABH-A	E5E5	4.704.70	4.374.37	(0.133, 0.088)(0.133, 0.088)	243243
비교예 6Comparative Example 6	BH-ABH-A	E6E6	4.524.52	4.014.01	(0.135, 0.089)(0.135, 0.089)	236236
비교예 7Comparative Example 7	BH-ABH-A	E7E7	4.464.46	4.214.21	(0.135, 0.087)(0.135, 0.087)	190190
비교예 8Comparative Example 8	BH-ABH-A	E8E8	4.494.49	4.104.10	(0.135, 0.088)(0.135, 0.088)	188188
비교예 9Comparative Example 9	BH-ABH-A	E9E9	4.524.52	4.034.03	(0.133, 0.088)(0.133, 0.088)	260260
비교예 10Comparative Example 10	BH-ABH-A	E10E10	4.504.50	4.044.04	(0.133, 0.088)(0.133, 0.088)	243243
비교예 11Comparative Example 11	BH-ABH-A	E11E11	4.424.42	4.084.08	(0.133, 0.088)(0.133, 0.088)	262262
비교예 12Comparative Example 12	BH-ABH-A	E12E12	4.544.54	3.923.92	(0.135, 0.089)(0.135, 0.089)	257257
비교예 13Comparative Example 13	BH-ABH-A	E13E13	4.444.44	4.094.09	(0.135, 0.087)(0.135, 0.087)	198198
비교예 14Comparative Example 14	BH-ABH-A	E14E14	4.484.48	4.074.07	(0.135, 0.088)(0.135, 0.088)	195195
비교예 15Comparative Example 15	BH-BBH-B	E1E1	4.504.50	3.983.98	(0.133, 0.088)(0.133, 0.088)	250250
비교예 16Comparative Example 16	BH-BBH-B	E2E2	4.514.51	4.104.10	(0.133, 0.088)(0.133, 0.088)	253253
비교예 17Comparative Example 17	BH-BBH-B	E3E3	4.404.40	4.004.00	(0.133, 0.088)(0.133, 0.088)	222222
비교예 18Comparative Example 18	BH-BBH-B	E4E4	4.464.46	4.174.17	(0.135, 0.089)(0.135, 0.089)	161161
비교예 19Comparative Example 19	BH-BBH-B	E5E5	4.704.70	4.244.24	(0.135, 0.088)(0.135, 0.088)	211211
비교예 20Comparative Example 20	BH-BBH-B	E6E6	4.504.50	4.014.01	(0.133, 0.088)(0.133, 0.088)	200200
비교예 21Comparative Example 21	BH-BBH-B	E7E7	4.444.44	4.214.21	(0.133, 0.088)(0.133, 0.088)	166166
비교예 22Comparative Example 22	BH-BBH-B	E8E8	4.464.46	4.004.00	(0.133, 0.088)(0.133, 0.088)	154154
비교예 23Comparative Example 23	BH-BBH-B	E9E9	4.504.50	4.004.00	(0.135, 0.089)(0.135, 0.089)	228228
비교예 24Comparative Example 24	BH-BBH-B	E10E10	4.504.50	4.034.03	(0.135, 0.089)(0.135, 0.089)	212212
비교예 25Comparative Example 25	BH-BBH-B	E11E11	4.414.41	4.044.04	(0.135, 0.087)(0.135, 0.087)	231231
비교예 26Comparative Example 26	BH-BBH-B	E12E12	4.534.53	3.883.88	(0.135, 0.088)(0.135, 0.088)	217217
비교예 27Comparative Example 27	BH-BBH-B	E13E13	4.424.42	4.004.00	(0.133, 0.088)(0.133, 0.088)	178178
비교예 28Comparative Example 28	BH-BBH-B	E14E14	4.474.47	4.014.01	(0.133, 0.088)(0.133, 0.088)	165165
비교예 29Comparative Example 29	BH-CBH-C	E1E1	4.564.56	3.883.88	(0.133, 0.088)(0.133, 0.088)	260260
비교예 30Comparative Example 30	BH-CBH-C	E2E2	4.554.55	4.004.00	(0.135, 0.089)(0.135, 0.089)	273273
비교예 31Comparative Example 31	BH-CBH-C	E3E3	4.434.43	3.923.92	(0.135, 0.087)(0.135, 0.087)	252252
비교예 32Comparative Example 32	BH-CBH-C	E4E4	4.494.49	4.084.08	(0.135, 0.088)(0.135, 0.088)	191191
비교예 33Comparative Example 33	BH-CBH-C	E5E5	4.724.72	4.204.20	(0.133, 0.088)(0.133, 0.088)	231231
비교예 34Comparative Example 34	BH-CBH-C	E6E6	4.534.53	4.004.00	(0.133, 0.088)(0.133, 0.088)	220220
비교예 35Comparative Example 35	BH-CBH-C	E7E7	4.484.48	4.114.11	(0.133, 0.088)(0.133, 0.088)	186186
비교예 36Comparative Example 36	BH-CBH-C	E8E8	4.494.49	3.903.90	(0.135, 0.089)(0.135, 0.089)	184184
비교예 37Comparative Example 37	BH-CBH-C	E9E9	4.544.54	3.883.88	(0.135, 0.087)(0.135, 0.087)	258258
비교예 38Comparative Example 38	BH-CBH-C	E10E10	4.524.52	3.833.83	(0.135, 0.088)(0.135, 0.088)	262262
비교예 39Comparative Example 39	BH-CBH-C	E11E11	4.434.43	3.743.74	(0.133, 0.088)(0.133, 0.088)	251251
비교예 40Comparative Example 40	BH-CBH-C	E12E12	4.554.55	3.583.58	(0.133, 0.088)(0.133, 0.088)	237237
비교예 41Comparative Example 41	BH-CBH-C	E13E13	4.464.46	3.603.60	(0.133, 0.088)(0.133, 0.088)	198198
비교예 42Comparative Example 42	BH-CBH-C	E14E14	4.494.49	3.413.41	(0.135, 0.089)(0.135, 0.089)	204204
비교예 43Comparative Example 43	BH-DBH-D	E1E1	4.404.40	4.034.03	(0.135, 0.088)(0.135, 0.088)	242242
비교예 44Comparative Example 44	BH-DBH-D	E2E2	4.534.53	3.883.88	(0.133, 0.088)(0.133, 0.088)	2222
비교예 45Comparative Example 45	BH-DBH-D	E3E3	4.424.42	4.014.01	(0.133, 0.088)(0.133, 0.088)	1818
비교예 46Comparative Example 46	BH-DBH-D	E4E4	4.464.46	4.004.00	(0.133, 0.088)(0.133, 0.088)	1717
비교예 47Comparative Example 47	BH-DBH-D	E5E5	4.554.55	3.883.88	(0.135, 0.089)(0.135, 0.089)	271271
비교예 48Comparative Example 48	BH-DBH-D	E6E6	4.554.55	4.014.01	(0.135, 0.089)(0.135, 0.089)	286286
비교예 49Comparative Example 49	BH-DBH-D	E7E7	4.464.46	3.933.93	(0.135, 0.087)(0.135, 0.087)	2626
비교예 50Comparative Example 50	BH-DBH-D	E8E8	4.494.49	4.094.09	(0.135, 0.088)(0.135, 0.088)	203203
비교예 51Comparative Example 51	BH-DBH-D	E9E9	4.734.73	4.214.21	(0.133, 0.088)(0.133, 0.088)	2424
비교예 52Comparative Example 52	BH-DBH-D	E10E10	4.534.53	4.004.00	(0.133, 0.088)(0.133, 0.088)	248248
비교예 53Comparative Example 53	BH-DBH-D	E11E11	4.474.47	4.104.10	(0.133, 0.088)(0.133, 0.088)	199199
비교예 54Comparative Example 54	BH-DBH-D	E12E12	4.494.49	3.903.90	(0.135, 0.089)(0.135, 0.089)	198198
비교예 55Comparative Example 55	BH-DBH-D	E13E13	4.534.53	3.893.89	(0.135, 0.087)(0.135, 0.087)	268268
비교예 56Comparative Example 56	BH-DBH-D	E14E14	4.524.52	3.833.83	(0.135, 0.088)(0.135, 0.088)	271271
비교예 57Comparative Example 57	H1H1	ET-AET-A	4.434.43	5.005.00	(0.133, 0.088)(0.133, 0.088)	7575
비교예 58Comparative Example 58	H1H1	ET-BET-B	4.564.56	5.075.07	(0.133, 0.088)(0.133, 0.088)	7474
비교예 59Comparative Example 59	H1H1	ET-CET-C	4.454.45	5.025.02	(0.133, 0.088)(0.133, 0.088)	9090
비교예 60Comparative Example 60	H1H1	ET-DET-D	4.604.60	5.105.10	(0.135, 0.089)(0.135, 0.089)	4141
비교예 61Comparative Example 61	H1H1	ET-EET-E	4.454.45	5.805.80	(0.135, 0.087)(0.135, 0.087)	3333
비교예 62Comparative Example 62	H1H1	ET-FET-F	5.105.10	3.113.11	(0.135, 0.088)(0.135, 0.088)	1616
비교예 63Comparative Example 63	H1H1	ET-GET-G	4.304.30	5.315.31	(0.133, 0.088)(0.133, 0.088)	5050
비교예 64Comparative Example 64	H2H2	ET-AET-A	4.334.33	4.944.94	(0.133, 0.088)(0.133, 0.088)	5555
비교예 65Comparative Example 65	H2H2	ET-BET-B	4.464.46	5.005.00	(0.133, 0.088)(0.133, 0.088)	5454
비교예 66Comparative Example 66	H2H2	ET-CET-C	4.354.35	4.924.92	(0.135, 0.089)(0.135, 0.089)	7171
비교예 67Comparative Example 67	H2H2	ET-DET-D	4.504.50	5.105.10	(0.135, 0.088)(0.135, 0.088)	2222
비교예 68Comparative Example 68	H2H2	ET-EET-E	4.354.35	5.225.22	(0.133, 0.088)(0.133, 0.088)	2121
비교예 69Comparative Example 69	H2H2	ET-FET-F	5.005.00	3.003.00	(0.133, 0.088)(0.133, 0.088)	1111
비교예 70Comparative Example 70	H2H2	ET-GET-G	4.204.20	5.115.11	(0.133, 0.088)(0.133, 0.088)	4444
비교예 71Comparative Example 71	H3H3	ET-AET-A	4.314.31	4.924.92	(0.135, 0.089)(0.135, 0.089)	5151
비교예 72Comparative Example 72	H3H3	ET-BET-B	4.404.40	5.015.01	(0.135, 0.089)(0.135, 0.089)	5050
비교예 73Comparative Example 73	H3H3	ET-CET-C	4.334.33	4.934.93	(0.135, 0.087)(0.135, 0.087)	6161
비교예 74Comparative Example 74	H3H3	ET-DET-D	4.524.52	5.115.11	(0.135, 0.088)(0.135, 0.088)	2525
비교예 75Comparative Example 75	H3H3	ET-EET-E	4.324.32	5.215.21	(0.133, 0.088)(0.133, 0.088)	1919
비교예 76Comparative Example 76	H3H3	ET-FET-F	5.015.01	3.013.01	(0.133, 0.088)(0.133, 0.088)	1414
비교예 77Comparative Example 77	H3H3	ET-GET-G	4.224.22	5.105.10	(0.133, 0.088)(0.133, 0.088)	3838
비교예 78Comparative Example 78	H4H4	ET-AET-A	4.304.30	4.944.94	(0.135, 0.089)(0.135, 0.089)	4444
비교예 79Comparative Example 79	H4H4	ET-BET-B	4.414.41	5.025.02	(0.135, 0.087)(0.135, 0.087)	4848
비교예 80Comparative Example 80	H4H4	ET-CET-C	4.314.31	4.914.91	(0.135, 0.088)(0.135, 0.088)	5454
비교예 81Comparative Example 81	H4H4	ET-DET-D	4.514.51	5.105.10	(0.133, 0.088)(0.133, 0.088)	3030
비교예 82Comparative Example 82	H4H4	ET-EET-E	4.334.33	5.225.22	(0.133, 0.088)(0.133, 0.088)	2424
비교예 83Comparative Example 83	H4H4	ET-FET-F	5.025.02	3.043.04	(0.133, 0.088)(0.133, 0.088)	1616
비교예 84Comparative Example 84	H4H4	ET-GET-G	4.244.24	5.135.13	(0.135, 0.089)(0.135, 0.089)	4141
비교예 85Comparative Example 85	H5H5	ET-AET-A	4.304.30	4.934.93	(0.135, 0.087)(0.135, 0.087)	6060
비교예 86Comparative Example 86	H5H5	ET-BET-B	4.414.41	5.025.02	(0.135, 0.088)(0.135, 0.088)	5757
비교예 87Comparative Example 87	H5H5	ET-CET-C	4.304.30	4.914.91	(0.133, 0.088)(0.133, 0.088)	6767
비교예 88Comparative Example 88	H5H5	ET-DET-D	4.514.51	5.105.10	(0.133, 0.088)(0.133, 0.088)	4444
비교예 89Comparative Example 89	H5H5	ET-EET-E	4.334.33	5.235.23	(0.133, 0.088)(0.133, 0.088)	3535
비교예 90Comparative Example 90	H5H5	ET-FET-F	5.015.01	3.013.01	(0.135, 0.089)(0.135, 0.089)	2222
비교예 91Comparative Example 91	H5H5	ET-GET-G	4.244.24	5.105.10	(0.135, 0.088)(0.135, 0.088)	7070
비교예 92Comparative Example 92	H6H6	ET-AET-A	4.314.31	4.924.92	(0.133, 0.088)(0.133, 0.088)	6262
비교예 93Comparative Example 93	H6H6	ET-BET-B	4.404.40	5.015.01	(0.133, 0.088)(0.133, 0.088)	5858
비교예 94Comparative Example 94	H6H6	ET-CET-C	4.304.30	4.914.91	(0.133, 0.088)(0.133, 0.088)	6060
비교예 95Comparative Example 95	H6H6	ET-DET-D	4.514.51	5.105.10	(0.135, 0.089)(0.135, 0.089)	4141
비교예 96Comparative Example 96	H6H6	ET-EET-E	4.324.32	5.225.22	(0.135, 0.089)(0.135, 0.089)	3131
비교예 97Comparative Example 97	H6H6	ET-FET-F	5.015.01	3.013.01	(0.135, 0.087)(0.135, 0.087)	2020
비교예 98Comparative Example 98	H6H6	ET-GET-G	4.234.23	5.115.11	(0.135, 0.088)(0.135, 0.088)	6161
비교예 99Comparative Example 99	H7H7	ET-AET-A	4.224.22	4.704.70	(0.133, 0.088)(0.133, 0.088)	6262
비교예 100Comparative Example 100	H7H7	ET-BET-B	4.194.19	4.844.84	(0.133, 0.088)(0.133, 0.088)	5858
비교예 101Comparative Example 101	H7H7	ET-CET-C	4.214.21	4.824.82	(0.133, 0.088)(0.133, 0.088)	6060
비교예 102Comparative Example 102	H7H7	ET-DET-D	4.44.4	4.874.87	(0.135, 0.089)(0.135, 0.089)	4141
비교예 103Comparative Example 103	H7H7	ET-EET-E	4.234.23	4.944.94	(0.135, 0.087)(0.135, 0.087)	3131
비교예 104Comparative Example 104	H7H7	ET-FET-F	4.894.89	3.113.11	(0.135, 0.088)(0.135, 0.088)	2020
비교예 105Comparative Example 105	H7H7	ET-GET-G	4.204.20	5.085.08	(0.133, 0.088)(0.133, 0.088)	6161
비교예 106Comparative Example 106	BH-EBH-E	E4E4	4.054.05	5.105.10	(0.135, 0.088)(0.135, 0.088)	181181
비교예 107Comparative Example 107	BH-FBH-F	E4E4	6.056.05	2.662.66	(0.135, 0.090)(0.135, 0.090)	6262
비교예 108Comparative Example 108	BH-GBH-G	E1E1	4.404.40	3.993.99	(0.135, 0.088)(0.135, 0.088)	247247
비교예 109Comparative Example 109	BH-GBH-G	E2E2	4.534.53	3.843.84	(0.133, 0.088)(0.133, 0.088)	2222
비교예 110Comparative Example 110	BH-GBH-G	E3E3	4.424.42	3.973.97	(0.133, 0.088)(0.133, 0.088)	1818
비교예 111Comparative Example 111	BH-GBH-G	E4E4	4.464.46	3.963.96	(0.133, 0.088)(0.133, 0.088)	1717
비교예 112Comparative Example 112	BH-GBH-G	E5E5	4.554.55	3.843.84	(0.135, 0.089)(0.135, 0.089)	276276
비교예 113Comparative Example 113	BH-GBH-G	E6E6	4.464.46	3.973.97	(0.135, 0.089)(0.135, 0.089)	292292
비교예 114Comparative Example 114	BH-GBH-G	E7E7	4.494.49	3.893.89	(0.135, 0.087)(0.135, 0.087)	2727
비교예 115Comparative Example 115	BH-GBH-G	E8E8	4.734.73	4.054.05	(0.135.0.088)(0.135.0.088)	207207
비교예 116Comparative Example 116	BH-GBH-G	E9E9	4.734.73	4.174.17	(0.133, 0.088)(0.133, 0.088)	2424
비교예 117Comparative Example 117	BH-GBH-G	E10E10	4.534.53	3.963.96	(0.133, 0.088)(0.133, 0.088)	253253
비교예 118Comparative Example 118	BH-GBH-G	E11E11	4.474.47	4.064.06	(0.133, 0.088)(0.133, 0.088)	203203
비교예 119Comparative Example 119	BH-GBH-G	E12E12	4.494.49	3.863.86	(0.135, 0.089)(0.135, 0.089)	2020
비교예 120Comparative Example 120	BH-GBH-G	E13E13	4.534.53	3.853.85	(0.135, 0.087)(0.135, 0.087)	273273
비교예 121Comparative Example 121	BH-GBH-G	E14E14	4.524.52	3.793.79	(0.135, 0.088)(0.135, 0.088)	276276

As described in Table 1 above, the compound represented by Formula 1 according to the present invention is included in the emission layer of an organic light emitting device, and the compound represented by Formula 2 can be used in an organic material layer capable of simultaneously injecting electrons and transporting electrons. have.

Comparing the Example of Table 1 with Comparative Examples 1 to 56 and Comparative Examples 108 to 121, the anthracene compound of Formula 1 according to the present invention is an organic light emitting device compared to the unsubstituted compound at the anthracene position 2 of Formula 1 It is remarkably excellent in terms of efficiency and lifetime

Comparing the Example of Table 1 with Comparative Examples 57 to 105, the heterocyclic compound of Formula 2 according to the present invention is significantly superior to the compound in which the cyano group is unsubstituted in terms of the lifespan of the organic light-emitting device.

If the Example of Table 1 and Comparative Examples 106 to 107 are compared, and Equation 1 is calculated from the results of Table 3 below, the compounds satisfying Equation 1 in Chemical Formulas 1 to 2 according to the present invention do not satisfy Equation 1. It is remarkably excellent in terms of efficiency and lifetime of an organic light-emitting device using a compound.

<< 실험예Experimental example 2> 2>

실시예Example 1 One

The HI-A compound was thermally vacuum deposited to a thickness of 600 Å on the prepared ITO transparent electrode to form a hole injection layer. 50 Å of the HAT compound and 60 Å of the HT-A compound were sequentially vacuum-deposited on the hole injection layer to form a hole transport layer.

Subsequently, the H1 compound and the BD compound with a film thickness of 200 Å were vacuum deposited on the hole transport layer at a weight ratio of 25:1 to form a light emitting layer.

Compound HBL-A was vacuum deposited on the emission layer to form a hole blocking layer with a thickness of 50 Å. Compound E1 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer.

In Example 1 of Experimental Example 2, the light emitting layer host (H1) and the electron injecting and transporting layer (E1) were changed to the compounds of Table 2 below, and the driving voltage and the driving voltage at a current density of 10 mA/cm ² The luminous efficiency was measured, and the time (T90) to be 90% of the initial luminance at a current density of 20 mA/cm ² was measured. The results are shown in Table 2 below.

구분(화합물)Classification (compound)			전압(V@10 mA/cm²)Voltage (V@10 mA/cm ² )	효율(cd/A@10 mA/cm²)Efficiency (cd/A@10 mA/cm ² )	색좌표(x, y)Color coordinates (x, y)	수명(h)(T90 at 20 mA/cm²)Life (h)(T90 at 20 mA/cm ² )
실시예 1 Example 1	H1H1	E1E1	4.054.05	6.506.50	(0.135, 0.089)(0.135, 0.089)	280280
실시예 2Example 2	H1H1	E2E2	4.004.00	6.666.66	(0.135, 0.087)(0.135, 0.087)	254254
실시예 3Example 3	H1H1	E3E3	4.034.03	6.556.55	(0.135, 0.088)(0.135, 0.088)	271271
실시예 4Example 4	H1H1	E4E4	4.094.09	6.826.82	(0.133, 0.088)(0.133, 0.088)	195195
실시예 5Example 5	H1H1	E5E5	4.214.21	6.206.20	(0.133, 0.088)(0.133, 0.088)	453453
실시예 6Example 6	H1H1	E6E6	4.034.03	6.626.62	(0.133, 0.088)(0.133, 0.088)	255255
실시예 7Example 7	H1H1	E7E7	3.983.98	6.826.82	(0.135, 0.089)(0.135, 0.089)	192192
실시예 8Example 8	H1H1	E8E8	3.973.97	6.806.80	(0.135, 0.087)(0.135, 0.087)	187187
실시예 9Example 9	H1H1	E9E9	4.034.03	6.636.63	(0.135, 0.088)(0.135, 0.088)	260260
실시예 10Example 10	H1H1	E10E10	4.014.01	6.676.67	(0.133, 0.088)(0.133, 0.088)	224224
실시예 11Example 11	H1H1	E11E11	3.963.96	6.706.70	(0.133, 0.088)(0.133, 0.088)	239239
실시예 12Example 12	H1H1	E12E12	4.074.07	6.526.52	(0.133, 0.088)(0.133, 0.088)	280280
실시예 13Example 13	H1H1	E13E13	3.983.98	6.806.80	(0.135, 0.089)(0.135, 0.089)	200200
실시예 14Example 14	H1H1	E14E14	3.953.95	6.776.77	(0.135, 0.087)(0.135, 0.087)	211211
실시예 15Example 15	H2H2	E1E1	4.004.00	6.546.54	(0.135, 0.088)(0.135, 0.088)	269269
실시예 16Example 16	H2H2	E2E2	3.943.94	6.676.67	(0.133, 0.088)(0.133, 0.088)	238238
실시예 17Example 17	H2H2	E3E3	3.963.96	6.576.57	(0.133, 0.088)(0.133, 0.088)	171171
실시예 18Example 18	H2H2	E4E4	3.933.93	6.856.85	(0.133, 0.088)(0.133, 0.088)	186186
실시예 19Example 19	H2H2	E5E5	4.174.17	6.416.41	(0.135, 0.089)(0.135, 0.089)	360360
실시예 20Example 20	H2H2	E6E6	3.993.99	6.676.67	(0.135, 0.087)(0.135, 0.087)	244244
실시예 21Example 21	H2H2	E7E7	3.923.92	6.896.89	(0.135, 0.088)(0.135, 0.088)	179179
실시예 22Example 22	H2H2	E8E8	3.953.95	6.856.85	(0.133, 0.088)(0.133, 0.088)	172172
실시예 23Example 23	H2H2	E9E9	4.004.00	6.646.64	(0.133, 0.088)(0.133, 0.088)	244244
실시예 24Example 24	H2H2	E10E10	4.014.01	6.666.66	(0.133, 0.088)(0.133, 0.088)	216216
실시예 25Example 25	H2H2	E11E11	3.903.90	6.736.73	(0.135, 0.089)(0.135, 0.089)	207207
실시예 26Example 26	H2H2	E12E12	4.034.03	6.556.55	(0.135, 0.087)(0.135, 0.087)	235235
실시예 27Example 27	H2H2	E13E13	3.923.92	6.826.82	(0.135, 0.088)(0.135, 0.088)	178178
실시예 28Example 28	H2H2	E14E14	3.913.91	6.816.81	(0.133, 0.088)(0.133, 0.088)	194194
실시예 29Example 29	H3H3	E1E1	3.943.94	6.516.51	(0.133, 0.088)(0.133, 0.088)	230230
실시예 30Example 30	H3H3	E2E2	3.853.85	6.626.62	(0.133, 0.088)(0.133, 0.088)	201201
실시예 31Example 31	H3H3	E3E3	3.933.93	6.506.50	(0.135, 0.089)(0.135, 0.089)	222222
실시예 32Example 32	H3H3	E4E4	3.913.91	6.766.76	(0.135, 0.087)(0.135, 0.087)	169169
실시예 33Example 33	H3H3	E5E5	4.104.10	6.396.39	(0.135, 0.088)(0.135, 0.088)	274274
실시예 34Example 34	H3H3	E6E6	3.913.91	6.566.56	(0.133, 0.088)(0.133, 0.088)	146146
실시예 35Example 35	H3H3	E7E7	3.883.88	6.786.78	(0.133, 0.088)(0.133, 0.088)	170170
실시예 36Example 36	H3H3	E8E8	3.893.89	6.776.77	(0.133, 0.088)(0.133, 0.088)	180180
실시예 37Example 37	H3H3	E9E9	3.923.92	6.606.60	(0.135, 0.089)(0.135, 0.089)	241241
실시예 38Example 38	H3H3	E10E10	3.953.95	6.646.64	(0.135, 0.087)(0.135, 0.087)	208208
실시예 39Example 39	H3H3	E11E11	3.873.87	6.726.72	(0.135, 0.088)(0.135, 0.088)	220220
실시예 40Example 40	H3H3	E12E12	3.893.89	6.556.55	(0.133, 0.088)(0.133, 0.088)	244244
실시예 41Example 41	H3H3	E13E13	3.903.90	6.746.74	(0.133, 0.088)(0.133, 0.088)	182182
실시예 42Example 42	H3H3	E14E14	3.913.91	6.806.80	(0.133, 0.088)(0.133, 0.088)	197197
실시예 43Example 43	H4H4	E1E1	3.923.92	6.506.50	(0.135, 0.089)(0.135, 0.089)	224224
실시예 44Example 44	H4H4	E2E2	3.873.87	6.616.61	(0.135, 0.087)(0.135, 0.087)	200200
실시예 45Example 45	H4H4	E3E3	3.903.90	6.526.52	(0.135, 0.088)(0.135, 0.088)	208208
실시예 46Example 46	H4H4	E4E4	3.893.89	6.806.80	(0.133, 0.088)(0.133, 0.088)	170170
실시예 47Example 47	H4H4	E5E5	4.114.11	6.306.30	(0.133, 0.088)(0.133, 0.088)	380380
실시예 48Example 48	H4H4	E6E6	3.923.92	6.566.56	(0.133, 0.088)(0.133, 0.088)	240240
실시예 49Example 49	H4H4	E7E7	3.883.88	6.746.74	(0.135, 0.089)(0.135, 0.089)	176176
실시예 50Example 50	H4H4	E8E8	3.873.87	6.766.76	(0.135, 0.089)(0.135, 0.089)	183183
실시예 51Example 51	H4H4	E9E9	3.903.90	6.616.61	(0.135, 0.087)(0.135, 0.087)	238238
실시예 52Example 52	H4H4	E10E10	3.933.93	6.626.62	(0.135, 0.088)(0.135, 0.088)	199199
실시예 53Example 53	H4H4	E11E11	3.863.86	6.706.70	(0.133, 0.088)(0.133, 0.088)	208208
실시예 54Example 54	H4H4	E12E12	3.853.85	6.546.54	(0.133, 0.088)(0.133, 0.088)	235235
실시예 55Example 55	H4H4	E13E13	3.883.88	6.726.72	(0.133, 0.088)(0.133, 0.088)	281281
실시예 56Example 56	H4H4	E14E14	3.883.88	6.806.80	(0.135, 0.089)(0.135, 0.089)	177177
실시예 57Example 57	H5H5	E1E1	3.903.90	6.516.51	(0.135, 0.087)(0.135, 0.087)	243243
실시예 58Example 58	H5H5	E2E2	3.803.80	6.606.60	(0.135, 0.088)(0.135, 0.088)	220220
실시예 59Example 59	H5H5	E3E3	3.903.90	6.536.53	(0.133, 0.088)(0.133, 0.088)	220220
실시예 60Example 60	H5H5	E4E4	3.893.89	6.816.81	(0.133, 0.088)(0.133, 0.088)	174174
실시예 61Example 61	H5H5	E5E5	4.114.11	6.396.39	(0.133, 0.088)(0.133, 0.088)	401401
실시예 62Example 62	H5H5	E6E6	3.903.90	6.546.54	(0.135, 0.089)(0.135, 0.089)	163163
실시예 63Example 63	H5H5	E7E7	3.863.86	6.736.73	(0.135, 0.087)(0.135, 0.087)	194194
실시예 64Example 64	H5H5	E8E8	3.853.85	6.556.55	(0.135, 0.088)(0.135, 0.088)	192192
실시예 65Example 65	H5H5	E9E9	3.903.90	6.606.60	(0.133, 0.088)(0.133, 0.088)	256256
실시예 66Example 66	H5H5	E10E10	3.933.93	6.626.62	(0.133, 0.088)(0.133, 0.088)	211211
실시예 67Example 67	H5H5	E11E11	3.883.88	6.726.72	(0.133, 0.088)(0.133, 0.088)	222222
실시예 68Example 68	H5H5	E12E12	3.893.89	6.536.53	(0.135, 0.089)(0.135, 0.089)	249249
실시예 69Example 69	H5H5	E13E13	3.893.89	6.716.71	(0.135, 0.088)(0.135, 0.088)	203203
실시예 70Example 70	H5H5	E14E14	3.863.86	6.826.82	(0.133, 0.088)(0.133, 0.088)	191191
실시예 71Example 71	H6H6	E1E1	3.913.91	6.516.51	(0.133, 0.088)(0.133, 0.088)	240240
실시예 72Example 72	H6H6	E2E2	3.843.84	6.606.60	(0.133, 0.088)(0.133, 0.088)	221221
실시예 73Example 73	H6H6	E3E3	3.913.91	6.516.51	(0.135, 0.089)(0.135, 0.089)	210210
실시예 74Example 74	H6H6	E4E4	3.883.88	6.806.80	(0.135, 0.089)(0.135, 0.089)	175175
실시예 75Example 75	H6H6	E5E5	4.104.10	6.416.41	(0.135, 0.087)(0.135, 0.087)	402402
실시예 76Example 76	H6H6	E6E6	3.913.91	6.566.56	(0.135, 0.088)(0.135, 0.088)	254254
실시예 77Example 77	H6H6	E7E7	3.853.85	6.746.74	(0.133, 0.088)(0.133, 0.088)	191191
실시예 78Example 78	H6H6	E8E8	3.883.88	6.736.73	(0.133, 0.088)(0.133, 0.088)	188188
실시예 79Example 79	H6H6	E9E9	3.903.90	6.616.61	(0.133, 0.088)(0.133, 0.088)	250250
실시예 80Example 80	H6H6	E10E10	3.943.94	6.606.60	(0.135, 0.089)(0.135, 0.089)	210210
실시예 81Example 81	H6H6	E11E11	3.843.84	6.716.71	(0.135, 0.087)(0.135, 0.087)	220220
실시예 82Example 82	H6H6	E12E12	3.863.86	6.546.54	(0.135, 0.088)(0.135, 0.088)	246246
실시예 83Example 83	H6H6	E13E13	3.863.86	6.716.71	(0.133, 0.088)(0.133, 0.088)	199199
실시예 84Example 84	H6H6	E14E14	3.863.86	6.816.81	(0.133, 0.088)(0.133, 0.088)	187187
실시예 85Example 85	H7H7	E1E1	3.793.79	6.326.32	(0.133, 0.088)(0.133, 0.088)	251251
실시예 86Example 86	H7H7	E2E2	3.753.75	6.536.53	(0.135, 0.089)(0.135, 0.089)	233233
실시예 87Example 87	H7H7	E3E3	3.783.78	6.436.43	(0.135, 0.087)(0.135, 0.087)	241241
실시예 88Example 88	H7H7	E4E4	3.823.82	6.616.61	(0.135, 0.088)(0.135, 0.088)	168168
실시예 89Example 89	H7H7	E5E5	3.903.90	6.186.18	(0.133, 0.088)(0.133, 0.088)	303303
실시예 90Example 90	H7H7	E6E6	3.803.80	6.516.51	(0.133, 0.088)(0.133, 0.088)	208208
실시예 91Example 91	H7H7	E7E7	3.803.80	6.616.61	(0.133, 0.088)(0.133, 0.088)	167167
실시예 92Example 92	H7H7	E8E8	3.813.81	6.606.60	(0.135, 0.089)(0.135, 0.089)	160160
실시예 93Example 93	H7H7	E9E9	3.873.87	6.436.43	(0.135, 0.088)(0.135, 0.088)	231231
실시예 94Example 94	H7H7	E10E10	3.773.77	6.446.44	(0.133, 0.088)(0.133, 0.088)	194194
실시예 95Example 95	H7H7	E11E11	3.813.81	6.506.50	(0.133, 0.088)(0.133, 0.088)	224224
실시예 96Example 96	H7H7	E12E12	3.843.84	6.336.33	(0.133, 0.088)(0.133, 0.088)	229229
실시예 97Example 97	H7H7	E13E13	3.813.81	6.506.50	(0.135, 0.089)(0.135, 0.089)	176176
실시예 98Example 98	H7H7	E14E14	3.793.79	6.576.57	(0.135, 0.089)(0.135, 0.089)	169169
실시예 99Example 99	H7H7	E15E15	3.843.84	6.226.22	(0.133, 0.088)(0.133, 0.088)	319319
실시예 100Example 100	H7H7	E16E16	3.813.81	6.406.40	(0.135, 0.089)(0.135, 0.089)	235235
실시예 101Example 101	H7H7	E17E17	3.793.79	5.975.97	(0.135, 0.087)(0.135, 0.087)	161161
비교예 1Comparative Example 1	BH-ABH-A	E1E1	4.254.25	4.404.40	(0.135, 0.087)(0.135, 0.087)	167167
비교예 2Comparative Example 2	BH-ABH-A	E2E2	4.204.20	4.514.51	(0.135, 0.088)(0.135, 0.088)	166166
비교예 3Comparative Example 3	BH-ABH-A	E3E3	4.134.13	4.404.40	(0.133, 0.088)(0.133, 0.088)	140140
비교예 4Comparative Example 4	BH-ABH-A	E4E4	4.294.29	4.514.51	(0.133, 0.088)(0.133, 0.088)	9191
비교예 5Comparative Example 5	BH-ABH-A	E5E5	4.404.40	4.774.77	(0.133, 0.088)(0.133, 0.088)	123123
비교예 6Comparative Example 6	BH-ABH-A	E6E6	4.224.22	4.414.41	(0.135, 0.089)(0.135, 0.089)	116116
비교예 7Comparative Example 7	BH-ABH-A	E7E7	4.264.26	4.614.61	(0.135, 0.087)(0.135, 0.087)	9090
비교예 8Comparative Example 8	BH-ABH-A	E8E8	4.194.19	4.604.60	(0.135, 0.088)(0.135, 0.088)	8888
비교예 9Comparative Example 9	BH-ABH-A	E9E9	4.224.22	4.434.43	(0.133, 0.088)(0.133, 0.088)	130130
비교예 10Comparative Example 10	BH-ABH-A	E10E10	4.204.20	4.544.54	(0.133, 0.088)(0.133, 0.088)	123123
비교예 11Comparative Example 11	BH-ABH-A	E11E11	4.114.11	4.484.48	(0.133, 0.088)(0.133, 0.088)	142142
비교예 12Comparative Example 12	BH-ABH-A	E12E12	4.254.25	4.424.42	(0.135, 0.089)(0.135, 0.089)	137137
비교예 13Comparative Example 13	BH-ABH-A	E13E13	4.164.16	4.494.49	(0.135, 0.087)(0.135, 0.087)	100100
비교예 14Comparative Example 14	BH-ABH-A	E14E14	4.184.18	4.504.50	(0.135, 0.088)(0.135, 0.088)	101101
비교예 15Comparative Example 15	BH-BBH-B	E1E1	4.204.20	4.484.48	(0.133, 0.088)(0.133, 0.088)	130130
비교예 16Comparative Example 16	BH-BBH-B	E2E2	4.214.21	4.504.50	(0.133, 0.088)(0.133, 0.088)	132132
비교예 17Comparative Example 17	BH-BBH-B	E3E3	4.104.10	4.454.45	(0.133, 0.088)(0.133, 0.088)	102102
비교예 18Comparative Example 18	BH-BBH-B	E4E4	4.164.16	4.574.57	(0.135, 0.089)(0.135, 0.089)	6666
비교예 19Comparative Example 19	BH-BBH-B	E5E5	4.504.50	4.644.64	(0.135, 0.088)(0.135, 0.088)	161161
비교예 20Comparative Example 20	BH-BBH-B	E6E6	4.204.20	4.414.41	(0.133, 0.088)(0.133, 0.088)	170170
비교예 21Comparative Example 21	BH-BBH-B	E7E7	4.144.14	4.614.61	(0.133, 0.088)(0.133, 0.088)	6666
비교예 22Comparative Example 22	BH-BBH-B	E8E8	4.164.16	4.404.40	(0.133, 0.088)(0.133, 0.088)	7474
비교예 23Comparative Example 23	BH-BBH-B	E9E9	4.204.20	4.504.50	(0.135, 0.089)(0.135, 0.089)	108108
비교예 24Comparative Example 24	BH-BBH-B	E10E10	4.214.21	4.434.43	(0.135, 0.089)(0.135, 0.089)	103103
비교예 25Comparative Example 25	BH-BBH-B	E11E11	4.114.11	4.454.45	(0.135, 0.087)(0.135, 0.087)	111111
비교예 26Comparative Example 26	BH-BBH-B	E12E12	4.224.22	4.394.39	(0.135, 0.088)(0.135, 0.088)	110110
비교예 27Comparative Example 27	BH-BBH-B	E13E13	4.124.12	4.454.45	(0.133, 0.088)(0.133, 0.088)	8989
비교예 28Comparative Example 28	BH-BBH-B	E14E14	4.174.17	4.464.46	(0.133, 0.088)(0.133, 0.088)	8585
비교예 29Comparative Example 29	BH-CBH-C	E1E1	4.254.25	4.404.40	(0.133, 0.088)(0.133, 0.088)	141141
비교예 30Comparative Example 30	BH-CBH-C	E2E2	4.254.25	4.504.50	(0.135, 0.089)(0.135, 0.089)	149149
비교예 31Comparative Example 31	BH-CBH-C	E3E3	4.134.13	4.424.42	(0.135, 0.087)(0.135, 0.087)	138138
비교예 32Comparative Example 32	BH-CBH-C	E4E4	4.184.18	4.584.58	(0.135, 0.088)(0.135, 0.088)	110110
비교예 33Comparative Example 33	BH-CBH-C	E5E5	4.424.42	4.704.70	(0.133, 0.088)(0.133, 0.088)	118118
비교예 34Comparative Example 34	BH-CBH-C	E6E6	4.234.23	4.504.50	(0.133, 0.088)(0.133, 0.088)	109109
비교예 35Comparative Example 35	BH-CBH-C	E7E7	4.184.18	4.514.51	(0.133, 0.088)(0.133, 0.088)	9090
비교예 36Comparative Example 36	BH-CBH-C	E8E8	4.194.19	4.404.40	(0.135, 0.089)(0.135, 0.089)	9292
비교예 37Comparative Example 37	BH-CBH-C	E9E9	4.234.23	4.384.38	(0.135, 0.087)(0.135, 0.087)	135135
비교예 38Comparative Example 38	BH-CBH-C	E10E10	4.234.23	4.334.33	(0.135, 0.088)(0.135, 0.088)	141141
비교예 39Comparative Example 39	BH-CBH-C	E11E11	4.144.14	4.144.14	(0.133, 0.088)(0.133, 0.088)	130130
비교예 40Comparative Example 40	BH-CBH-C	E12E12	4.264.26	3.983.98	(0.133, 0.088)(0.133, 0.088)	118118
비교예 41Comparative Example 41	BH-CBH-C	E13E13	4.164.16	4.124.12	(0.133, 0.088)(0.133, 0.088)	9999
비교예 42Comparative Example 42	BH-CBH-C	E14E14	4.194.19	3.953.95	(0.135, 0.089)(0.135, 0.089)	104104
비교예 43Comparative Example 43	BH-DBH-D	E1E1	4.104.10	4.534.53	(0.135, 0.088)(0.135, 0.088)	122122
비교예 44Comparative Example 44	BH-DBH-D	E2E2	4.234.23	5.305.30	(0.133, 0.088)(0.133, 0.088)	1919
비교예 45Comparative Example 45	BH-DBH-D	E3E3	4.124.12	4.514.51	(0.133, 0.088)(0.133, 0.088)	1515
비교예 46Comparative Example 46	BH-DBH-D	E4E4	4.164.16	4.504.50	(0.133, 0.088)(0.133, 0.088)	1414
비교예 47Comparative Example 47	BH-DBH-D	E5E5	4.254.25	4.384.38	(0.135, 0.089)(0.135, 0.089)	147147
비교예 48Comparative Example 48	BH-DBH-D	E6E6	4.254.25	4.514.51	(0.135, 0.089)(0.135, 0.089)	160160
비교예 49Comparative Example 49	BH-DBH-D	E7E7	4.154.15	4.504.50	(0.135, 0.087)(0.135, 0.087)	2121
비교예 50Comparative Example 50	BH-DBH-D	E8E8	4.204.20	4.494.49	(0.135, 0.088)(0.135, 0.088)	103103
비교예 51Comparative Example 51	BH-DBH-D	E9E9	4.434.43	4.614.61	(0.133, 0.088)(0.133, 0.088)	2121
비교예 52Comparative Example 52	BH-DBH-D	E10E10	4.234.23	4.504.50	(0.133, 0.088)(0.133, 0.088)	128128
비교예 53Comparative Example 53	BH-DBH-D	E11E11	4.174.17	4.604.60	(0.133, 0.088)(0.133, 0.088)	8989
비교예 54Comparative Example 54	BH-DBH-D	E12E12	4.194.19	4.404.40	(0.135, 0.089)(0.135, 0.089)	9898
비교예 55Comparative Example 55	BH-DBH-D	E13E13	4.234.23	4.414.41	(0.135, 0.087)(0.135, 0.087)	141141
비교예 56Comparative Example 56	BH-DBH-D	E14E14	4.224.22	4.334.33	(0.135, 0.088)(0.135, 0.088)	149149
비교예 57Comparative Example 57	H1H1	ET-AET-A	4.144.14	5.605.60	(0.133, 0.088)(0.133, 0.088)	5252
비교예 58Comparative Example 58	H1H1	ET-BET-B	4.254.25	5.575.57	(0.133, 0.088)(0.133, 0.088)	5151
비교예 59Comparative Example 59	H1H1	ET-CET-C	4.204.20	5.625.62	(0.133, 0.088)(0.133, 0.088)	6262
비교예 60Comparative Example 60	H1H1	ET-DET-D	4.304.30	5.605.60	(0.135, 0.089)(0.135, 0.089)	3737
비교예 61Comparative Example 61	H1H1	ET-EET-E	4.164.16	6.306.30	(0.135, 0.087)(0.135, 0.087)	3030
비교예 62Comparative Example 62	H1H1	ET-FET-F	4.814.81	4.014.01	(0.135, 0.088)(0.135, 0.088)	1010
비교예 63Comparative Example 63	H1H1	ET-GET-G	4.024.02	5.815.81	(0.133, 0.088)(0.133, 0.088)	4141
비교예 64Comparative Example 64	H2H2	ET-AET-A	4.034.03	5.545.54	(0.133, 0.088)(0.133, 0.088)	4949
비교예 65Comparative Example 65	H2H2	ET-BET-B	4.164.16	5.505.50	(0.133, 0.088)(0.133, 0.088)	4848
비교예 66Comparative Example 66	H2H2	ET-CET-C	4.054.05	5.425.42	(0.135, 0.089)(0.135, 0.089)	6767
비교예 67Comparative Example 67	H2H2	ET-DET-D	4.204.20	5.605.60	(0.135, 0.088)(0.135, 0.088)	1818
비교예 68Comparative Example 68	H2H2	ET-EET-E	4.054.05	5.735.73	(0.133, 0.088)(0.133, 0.088)	1919
비교예 69Comparative Example 69	H2H2	ET-FET-F	4.604.60	4.004.00	(0.133, 0.088)(0.133, 0.088)	1010
비교예 70Comparative Example 70	H2H2	ET-GET-G	3.903.90	5.705.70	(0.133, 0.088)(0.133, 0.088)	3737
비교예 71Comparative Example 71	H3H3	ET-AET-A	4.014.01	5.605.60	(0.135, 0.089)(0.135, 0.089)	4545
비교예 72Comparative Example 72	H3H3	ET-BET-B	4.104.10	5.515.51	(0.135, 0.089)(0.135, 0.089)	4444
비교예 73Comparative Example 73	H3H3	ET-CET-C	4.034.03	5.615.61	(0.135, 0.087)(0.135, 0.087)	5555
비교예 74Comparative Example 74	H3H3	ET-DET-D	4.224.22	5.615.61	(0.135, 0.088)(0.135, 0.088)	2222
비교예 75Comparative Example 75	H3H3	ET-EET-E	4.024.02	5.715.71	(0.133, 0.088)(0.133, 0.088)	1111
비교예 76Comparative Example 76	H3H3	ET-FET-F	4.554.55	3.813.81	(0.133, 0.088)(0.133, 0.088)	1010
비교예 77Comparative Example 77	H3H3	ET-GET-G	3.993.99	5.705.70	(0.133, 0.088)(0.133, 0.088)	3131
비교예 78Comparative Example 78	H4H4	ET-AET-A	4.004.00	5.645.64	(0.135, 0.089)(0.135, 0.089)	3838
비교예 79Comparative Example 79	H4H4	ET-BET-B	4.114.11	5.625.62	(0.135, 0.087)(0.135, 0.087)	3838
비교예 80Comparative Example 80	H4H4	ET-CET-C	4.014.01	5.515.51	(0.135, 0.088)(0.135, 0.088)	4444
비교예 81Comparative Example 81	H4H4	ET-DET-D	4.214.21	5.705.70	(0.133, 0.088)(0.133, 0.088)	2020
비교예 82Comparative Example 82	H4H4	ET-EET-E	4.034.03	5.585.58	(0.133, 0.088)(0.133, 0.088)	2121
비교예 83Comparative Example 83	H4H4	ET-FET-F	4.644.64	3.943.94	(0.133, 0.088)(0.133, 0.088)	1414
비교예 84Comparative Example 84	H4H4	ET-GET-G	3.913.91	5.695.69	(0.135, 0.089)(0.135, 0.089)	3131
비교예 85Comparative Example 85	H5H5	ET-AET-A	4.004.00	5.555.55	(0.135, 0.087)(0.135, 0.087)	5050
비교예 86Comparative Example 86	H5H5	ET-BET-B	4.114.11	5.525.52	(0.135, 0.088)(0.135, 0.088)	4747
비교예 87Comparative Example 87	H5H5	ET-CET-C	4.004.00	5.415.41	(0.133, 0.088)(0.133, 0.088)	5757
비교예 88Comparative Example 88	H5H5	ET-DET-D	4.214.21	5.605.60	(0.133, 0.088)(0.133, 0.088)	3434
비교예 89Comparative Example 89	H5H5	ET-EET-E	4.034.03	5.735.73	(0.133, 0.088)(0.133, 0.088)	2929
비교예 90Comparative Example 90	H5H5	ET-FET-F	4.584.58	3.813.81	(0.135, 0.089)(0.135, 0.089)	1919
비교예 91Comparative Example 91	H5H5	ET-GET-G	3.953.95	5.705.70	(0.135, 0.088)(0.135, 0.088)	5858
비교예 92Comparative Example 92	H6H6	ET-AET-A	4.014.01	5.625.62	(0.133, 0.088)(0.133, 0.088)	5454
비교예 93Comparative Example 93	H6H6	ET-BET-B	4.104.10	5.615.61	(0.133, 0.088)(0.133, 0.088)	4848
비교예 94Comparative Example 94	H6H6	ET-CET-C	4.004.00	5.515.51	(0.133, 0.088)(0.133, 0.088)	5050
비교예 95Comparative Example 95	H6H6	ET-DET-D	4.214.21	5.605.60	(0.135, 0.089)(0.135, 0.089)	3434
비교예 96Comparative Example 96	H6H6	ET-EET-E	4.024.02	5.725.72	(0.135, 0.089)(0.135, 0.089)	2626
비교예 97Comparative Example 97	H6H6	ET-FET-F	4.694.69	3.813.81	(0.135, 0.087)(0.135, 0.087)	1515
비교예 98Comparative Example 98	H6H6	ET-GET-G	3.943.94	5.715.71	(0.135, 0.088)(0.135, 0.088)	5252
비교예 99Comparative Example 99	H7H7	ET-AET-A	3.953.95	5.305.30	(0.133, 0.088)(0.133, 0.088)	5353
비교예 100Comparative Example 100	H7H7	ET-BET-B	3.903.90	5.415.41	(0.133, 0.088)(0.133, 0.088)	4848
비교예 101Comparative Example 101	H7H7	ET-CET-C	3.923.92	5.405.40	(0.133, 0.088)(0.133, 0.088)	5050
비교예 102Comparative Example 102	H7H7	ET-DET-D	4.104.10	5.395.39	(0.135, 0.089)(0.135, 0.089)	3131
비교예 103Comparative Example 103	H7H7	ET-EET-E	3.923.92	5.515.51	(0.135, 0.087)(0.135, 0.087)	2828
비교예 104Comparative Example 104	H7H7	ET-FET-F	4.494.49	3.713.71	(0.135, 0.088)(0.135, 0.088)	1717
비교예 105Comparative Example 105	H7H7	ET-GET-G	3.903.90	5.685.68	(0.133, 0.088)(0.133, 0.088)	5454
비교예 106Comparative Example 106	BH-EBH-E	E4E4	3.823.82	4.614.61	(0.135, 0.088)(0.135, 0.088)	8888
비교예 107Comparative Example 107	BH-FBH-F	E4E4	5.825.82	2.612.61	(0.135, 0.088)(0.135, 0.088)	1212
비교예 108Comparative Example 108	BH-GBH-G	E1E1	4.14.1	4.484.48	(0.135, 0.088)(0.135, 0.088)	124124
비교예 109Comparative Example 109	BH-GBH-G	E2E2	4.234.23	5.255.25	(0.133, 0.088)(0.133, 0.088)	1919
비교예 110Comparative Example 110	BH-GBH-G	E3E3	4.124.12	4.464.46	(0.133, 0.088)(0.133, 0.088)	1515
비교예 111Comparative Example 111	BH-GBH-G	E4E4	4.164.16	4.464.46	(0.133, 0.088)(0.133, 0.088)	1414
비교예 112Comparative Example 112	BH-GBH-G	E5E5	4.254.25	4.344.34	(0.135, 0.089)(0.135, 0.089)	150150
비교예 113Comparative Example 113	BH-GBH-G	E6E6	4.254.25	4.464.46	(0.135, 0.089)(0.135, 0.089)	163163
비교예 114Comparative Example 114	BH-GBH-G	E7E7	4.154.15	4.464.46	(0.135, 0.087)(0.135, 0.087)	2121
비교예 115Comparative Example 115	BH-GBH-G	E8E8	4.24.2	4.454.45	(0.135.0.088)(0.135.0.088)	105105
비교예 116Comparative Example 116	BH-GBH-G	E9E9	4.434.43	4.564.56	(0.133, 0.088)(0.133, 0.088)	2121
비교예 117Comparative Example 117	BH-GBH-G	E10E10	4.234.23	4.464.46	(0.133, 0.088)(0.133, 0.088)	131131
비교예 118Comparative Example 118	BH-GBH-G	E11E11	4.174.17	4.554.55	(0.133, 0.088)(0.133, 0.088)	9191
비교예 119Comparative Example 119	BH-GBH-G	E12E12	4.194.19	4.364.36	(0.135, 0.089)(0.135, 0.089)	100100
비교예 120Comparative Example 120	BH-GBH-G	E13E13	4.234.23	4.374.37	(0.135, 0.087)(0.135, 0.087)	144144
비교예 121Comparative Example 121	BH-GBH-G	E14E14	4.224.22	4.294.29	(0.135, 0.088)(0.135, 0.088)	152152

As shown in Table 2, the compound represented by Formula 1 according to the present invention is included in the emission layer of an organic light emitting device, and the compound represented by Formula 2 can be used in an organic material layer capable of simultaneously injecting electrons and transporting electrons. have.

Comparing the Examples of Table 2 with Comparative Examples 1 to 56 and Comparative Examples 108 to 121, the anthracene compound of Formula 1 according to the present invention is an organic light emitting device compared to the unsubstituted compound at the anthracene position 2 of Formula 1 It is remarkably excellent in terms of efficiency and lifetime

Comparing the Example of Table 2 with Comparative Examples 57 to 105, the heterocyclic compound of Formula 2 according to the present invention is significantly superior to the unsubstituted compound of a cyano group in terms of the lifespan of the organic light-emitting device.

When the Example of Table 2 and Comparative Examples 106 to 107 are compared, and Equation 1 is calculated from the results of Table 3 below, an organic light-emitting device using a compound satisfying Formula 1 to 2 and Formula 1 according to the present invention Even if it satisfies Formula 1 and Formula 2, it is remarkably superior in terms of efficiency and lifetime compared to an organic light-emitting device using a compound that does not satisfy Formula 1.

<< 실험예Experimental example 3> 3>

Compounds H1 to H7, E1 to E17, BH-A to BH-G, and ET-A to ET-G Dipole Moment (Debye) values according to an exemplary embodiment of the present specification are shown in Table 3 below.

화합물compound	Dipole Moment (Dipole Moment ( DebyeDebye ))
H1H1	0.160.16
H2H2	0.30.3
H3H3	0.30.3
H4H4	0.150.15
H5H5	0.150.15
H6H6	0.150.15
H7H7	0.760.76
E1E1	5.545.54
E2E2	5.175.17
E3E3	4.084.08
E4E4	3.733.73
E5E5	5.285.28
E6E6	5.565.56
E7E7	5.475.47
E8E8	5.845.84
E9E9	6.876.87
E10E10	6.866.86
E11E11	6.366.36
E12E12	5.385.38
E13E13	6.306.30
E14E14	5.015.01
E15E15	5.785.78
E16E16	4.664.66
E17E17	8.248.24
BH-ABH-A	0.00.0
BH-BBH-B	0.20.2
BH-CBH-C	0.00.0
BH-DBH-D	0.00.0
BH-EBH-E	2.972.97
BH-FBH-F	3.693.69
BH-GBH-G	0.00.0
ET-AET-A	0.650.65
ET-BET-B	0.560.56
ET-CET-C	0.480.48
ET-DET-D	0.220.22
ET-EET-E	0.320.32
ET-FET-F	3.353.35
ET-GET-G	0.820.82

The Dipole Moment (Debye) was performed using Gaussian 03, a quantum chemistry calculation program manufactured by Gaussian, USA, and using density functional theory (DFT), B3LYP as a functional function and 6-31G* as a basis function. The triplet energy was calculated using the time-dependent density functional theory (TD-DFT) for the structure optimized using.

Due to the high dipole moment value of the electron transport layer, electrons transferred to the light emitting layer are controlled, contributing to the improvement of the efficiency and lifespan of the organic light emitting device. It can be seen that the efficiency and life of the light emitting device are improved.

Claims

Anode; Cathode; And an emission layer provided between the anode and the cathode,

The emission layer includes a compound represented by Formula 1 below,

The organic light-emitting device further includes a first organic material layer comprising a compound represented by Formula 2 below between the emission layer and the cathode,

An organic light-emitting device that satisfies the following Formula 1:

[Formula 1]

[Formula 2]

In Formula 1,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,

Ar3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

R1 is hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

m is an integer from 0 to 7,

When m is 2 or more, R1 is the same as or different from each other,

In Formula 2,

X1 to X3 are N or CR, and at least one of X1 to X3 is N,

R is hydrogen or deuterium, or can be combined with adjacent Ar5 or Ar6 to form a ring,

Ar5 and Ar6 not bonded to R are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L5 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

L6 is a direct bond; -O-; A substituted or unsubstituted arylene group; A divalent or trivalent substituted or unsubstituted heterocyclic group; Or a trivalent substituted or unsubstituted aryl group,

L7 is a substituted or unsubstituted arylene group; A substituted or unsubstituted heteroarylene group; A trivalent substituted or unsubstituted aryl group; Or a trivalent heterocyclic group,

a and c are each 1 or 2, a+c≤3, b is 1 or 2,

When a to c are each 2, the structures in parentheses are the same as or different from each other,

n is an integer of 1 to 3,

[Equation 1]

P EI - P H > 1.0

In Formula 1, P H refers to the dipole moment value of the compound of Formula 1, and P EI Means the dipole moment value of the compound of Formula 2.
The method according to claim 1,

The first organic material layer is an organic light emitting device provided in contact with the emission layer.
The organic light-emitting device of claim 1, wherein the emission layer is a blue emission layer.
The method according to claim 1, wherein the first organic material layer is an electron transport layer; Or an organic light emitting device that is an electron injection and transport layer.
The method according to claim 1, wherein the first organic material layer is an electron transport layer; Or an electron injection and transport layer, wherein the organic light-emitting device further includes a hole blocking layer between the first organic material layer and the light-emitting layer.
The method according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with deuterium; A phenanthrene group unsubstituted or substituted with deuterium; Biphenyl group unsubstituted or substituted with deuterium; Or an organic light-emitting device that is a terphenyl group unsubstituted or substituted with deuterium.
The method according to claim 1, wherein Ar3 is a phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with deuterium; A phenanthrene group unsubstituted or substituted with deuterium; Biphenyl group unsubstituted or substituted with deuterium; Terphenyl group unsubstituted or substituted with deuterium; Dibenzofuran group; Or an organic light emitting device that is a dibenzothiophene group.
The method according to claim 1, wherein L1 to L3 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or an organic light emitting device that is a naphthylene group.
The method according to claim 1, wherein Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted pyridine group; Or an organic light-emitting device that is a substituted or unsubstituted spirofluorenexanthene group.
The method according to claim 1, wherein a and c are 1, and L5 and L7 are the same as or different from each other, and each independently a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted divalent terphenyl group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent fluorenyl group; A substituted or unsubstituted divalent dibenzofuran group; A substituted or unsubstituted divalent dibenzothiophene group; Or an organic light-emitting device that is a substituted or unsubstituted divalent spirofluoroxanthene group.
The organic light-emitting device of claim 1, wherein the compound represented by Formula 1 is selected from the following structural formula:

.
The organic light-emitting device of claim 1, wherein the compound represented by Formula 2 is selected from the following structural formula:

.
The organic light-emitting device of claim 1, wherein the light-emitting layer further comprises a compound represented by Formula 3 below:

[Formula 3]

In Chemical Formula 3,

X10 is B or P(=O),

Y1 is O, S or NRa, Y2 is O, S or NRb,

Cy1 to Cy3 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,

Ra is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with Cy1 or Cy3 to form a substituted or unsubstituted ring,

Rb is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with Cy2 or Cy3 to form a substituted or unsubstituted ring.
The organic light-emitting device of claim 1, further comprising at least one additional light-emitting layer between the anode and the cathode.
The organic light-emitting device of claim 14, wherein the light-emitting layer and the at least one additional light-emitting layer have different maximum emission wavelengths.
The organic light-emitting device of claim 14, wherein the light-emitting layer and the one or more additional light-emitting layers are arranged in a vertical or horizontal direction on a surface facing the anode and the cathode.
The organic light-emitting device of claim 14, wherein any one of the light-emitting layer and one or more additional light-emitting layers includes a fluorescent dopant, and any one of the remaining light-emitting layers includes a phosphorescent dopant.
The method according to claim 1, further comprising a second light emitting layer between the light emitting layer and the anode, further comprising a third light emitting layer between the second light emitting layer and the anode,

The emission layer, the second emission layer, and the third emission layer are blue fluorescent emission layers.
The method according to claim 1, wherein when R is not bonded to Ar5 or Ar6, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

When R is bonded to Ar5 or Ar6, Ar5 or Ar6 not bonded is hydrogen; A substituted or unsubstituted aryl group; Or an organic light-emitting device that is a substituted or unsubstituted heteroaryl group.
The method according to claim 1,

if a is 1 and c is 1,

b is 1 or 2, L7 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, and when b is 2, L7 is the same as or different from each other,

L6 is a direct bond; -O-; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

if a is 1 and c is 2,

b is 1, L7 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

L6 is a trivalent substituted or unsubstituted aryl group,

if a is 2 and c is 1,

b is 1, L7 is a trivalent substituted or unsubstituted aryl group; Or a trivalent heterocyclic group, and L6 is a direct bond; -O-; A substituted or unsubstituted arylene group; Or an organic light-emitting device that is a substituted or unsubstituted heteroarylene group.