WO2020111728A1

WO2020111728A1 - Organic light emitting device

Info

Publication number: WO2020111728A1
Application number: PCT/KR2019/016364
Authority: WO
Inventors: 허동욱; 홍성길; 허정오; 한미연; 이재탁; 양정훈
Original assignee: 주식회사 엘지화학
Priority date: 2018-11-26
Filing date: 2019-11-26
Publication date: 2020-06-04
Also published as: KR102271482B1; KR20200062066A; CN112585776A

Abstract

The present specification provides an organic light emitting device comprising a first organic layer and a second organic layer.

Description

Organic light emitting diode

This specification relates to an organic light emitting device.

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0147239 filed with the Korean Intellectual Property Office on November 26, 2018, the entire contents of which are incorporated herein.

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it glows.

The development of new materials for such organic light emitting devices continues to be required.

In the present specification, the compound represented by Formula 1 is included in the first organic material layer, and the compound represented by Formula 2 is included in the second organic material layer, so that the driving voltage is low, the efficiency is high, the lifetime characteristics are excellent, or the color purity is high. It is intended to provide a device.

This specification is an anode; cathode; An organic light emitting device comprising a first organic material layer and a second organic material layer provided between the anode and the cathode,

The first organic material layer includes a compound represented by Formula 1 below,

The second organic material layer provides an organic light emitting device comprising a compound represented by the following Chemical Formula 2.

[Formula 1]

In Chemical Formula 1,

X is B; P=O; Or P=S,

Z1 to Z3 are the same as or different from each other, and each independently a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring,

A1 is N(R101) or O, A2 is N(R102) or O,

R101 and R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

[Formula 2]

In Chemical Formula 2,

Y is O; Or S,

R21 to R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, represented by the following formula (3), or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

At least one of R21 to R24 is represented by the following formula (3),

r21 to r24 are the same or different from each other, each independently an integer of 0 to 4, and when r21 is 2 or more, R21 is the same or different from each other, and when r22 is 2 or more, R22 is the same or different from each other, and r23 is 2 or more. R23 is the same or different from each other, and when r24 is 2 or more, R24 is the same or different from each other,

[Formula 3]

In Chemical Formula 3,

X1 is N or C(R31), X2 is N or C(R32), X3 is N or C(R33), and one or more of X1 to X3 is N,

R31, R32 and R33 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted aromatic hydrocarbon ring in combination with Ar1 or Ar2; Or form a substituted or unsubstituted heteroring,

Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with R41; Or a heterocyclic group unsubstituted or substituted with R42, or an aromatic hydrocarbon ring substituted or unsubstituted with R31, R32 or R33; Or form a substituted or unsubstituted heteroring,

R41 and R42 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; Alkyl groups; Haloalkyl group; Alkoxy groups; Silyl group; Aryl group; And a heterocyclic group, or two or more substituents are connected,

L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

m is an integer from 0 to 4, and when 2 or more, L is the same or different from each other

* Is a site that binds to Formula 2.

The organic light emitting diode according to the exemplary embodiment of the present specification includes a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2, has excellent long life characteristics, has high efficiency characteristics, and has a low driving voltage.

1 to 4 show examples of the organic light emitting device of the present invention.

[Description of codes]

0: substrate

1: Cathode

2: electron transport layer

3: hole transport layer

4: anode

5: organic layer

6: Organic layer

7: hole blocking layer or electronic control layer

11: light emitting layer 1

12: light emitting layer 2

13: light emitting layer 3

101: emitting layer

201: first organic material layer

202: second organic layer

Hereinafter, the present specification will be described in more detail. However, the following description relates to an exemplary embodiment of the present invention, and includes all the ranges that can be substituted within an equivalent range.

First, some terms in the specification are clarified.

In the present specification, when a part is to “include” a certain component, it means that the component may further include other components, not to exclude other components, unless otherwise stated.

In the present specification, Cn refers to n carbon atoms.

In the present specification, Cn1-Cn2 refers to n1 to n2 carbon atoms.

Examples of substituents in the present specification are described below, but are not limited thereto.

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 to a position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and when two or more are substituted , 2 or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitrile group; Alkyl groups; Haloalkyl group; Alkoxy groups; Haloalkoxy groups; Cycloalkyl group; Silyl group; Alkenyl group; Amine group; Arylamine group; Aryl group; And one or more substituents selected from the group consisting of a heterocyclic group containing one or more of N, O, S, Se, and Si atoms, or substituted with a substituent linked by two or more substituents among the exemplified substituents, or any It means that it does not have a substituent. For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

In the present specification, that two or more substituents are connected means that hydrogen of one substituent is connected to another substituent. For example, an isopropyl group and a phenyl group are connected

or

It can be a substituent of.

In the present specification, (substituent 1)-(substituent 2)-(substituent 3) is connected not only continuously, but also (substituent 1) (substituent 2) and (substituent 3) are connected Includes connections. For example, two phenyl groups and isopropyl groups are connected

or

It can be a substituent of. The same applies to those above which four or more substituents are connected.

In this specification, * or

Means a site that is attached to another substituent or linkage.

In one embodiment of the present specification, “substituted or unsubstituted” means deuterium; Halogen group; Nitrile group; C1-C20 alkyl group; C1-C20 haloalkyl group; C1-C20Alkoxy group; C1-C20 haloalkoxy group; C3-C20 cycloalkyl group; C1-C50 silyl group; C2-C20Alkenyl group; Amine group; C6-C50 arylamine group; C6-C30Aryl group; And C2-C30 heterocyclic groups including one or more of N, O, S, Se, and Si atoms, substituted with 1 or 2 or more substituents, or substituted with 2 or more substituents, or having no substituents. Say things.

In one embodiment of the present specification, “substituted or unsubstituted” is one substituent selected from the group consisting of deuterium, a C1-C10 alkyl group, a C6-C30 aryl group, and a C2-C30 heterocyclic group, or two or more substituents. It means that the substituent is substituted with a connected substituent or does not have any substituent.

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

In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is 1 to 30; 1 to 20; 1 to 10; Or it is preferably 1 to 5. Specific examples are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentyl Methyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1 -Dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the haloalkyl group may be a straight chain or a branched chain, and the hydrogen of the aforementioned alkyl group is substituted with one or two or more halogen groups. Carbon number is not particularly limited, but is 1 to 30; 1 to 20; 1 to 10; Or it is preferably 1 to 5. The description of the alkyl group described above may be applied to the alkyl group. Specific examples of haloalkyl groups include, but are not limited to, fluoromethyl groups, difluoromethyl groups, trifluoromethyl groups, chloromethyl groups, dichloromethyl groups, trichloromethyl groups, bromomethyl groups, dibromomethyl groups, tribromomethyl groups, and the like. Does not work.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and 3 to 30; 3 to 15; Or 3 to 6 are more preferable. 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 is not limited thereto.

In the present specification, the alkoxy group is an alkyl group connected to an oxygen atom, and may be a straight chain, branched chain, or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is 1 to 30; 1 to 20; 1 to 10; Or it is preferably 1 to 5. 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. It may be, but is not limited to this.

In the present specification, the alkenyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is 2 to 30; 2 to 20; 2 to 10; Or it is preferably 2 to 5. 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 silyl group may be represented by the formula of -SiRaRbRc, wherein Ra, Rb and Rc are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. Does not.

In the present specification, the amine group may be represented by the formula of -NRfRg, wherein Rf and Rg are each hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heterocyclic group. The amine group is an alkylamine group; Arylalkylamine groups; Arylamine group; Aryl heteroarylamine group; Alkyl heteroarylamine groups; And a heteroarylamine group, and more specifically, a dimethylamine group; Diphenylamine group; And the like, but is not limited to these.

In this specification, an aryl group means a monovalent aromatic hydrocarbon or a monovalent group of an aromatic hydrocarbon derivative. In the present specification, an aromatic hydrocarbon means a compound including a ring in which pi electrons are completely conjugated and planar, and a group derived from an aromatic hydrocarbon means a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed in an aromatic hydrocarbon. . In addition, in the present specification, the aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are connected to each other. The aryl group is not particularly limited, and has 6 to 50 carbon atoms; 6 to 30; 6 to 25; 6 to 20; 6 to 18; Or it is preferably 6 to 13, the aryl group may be monocyclic or polycyclic. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, but is not limited thereto.

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

In the present specification, when it is said that the fluorenyl group may be substituted, the substituted fluorenyl group includes all compounds in which the substituents of the pentane ring of fluorene are spiro-bonded to each other to form an aromatic hydrocarbon ring. The substituted fluorenyl group includes 9,9'-spirobifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc. However, it is not limited to this.

In the present specification, a heteroaryl group means a monovalent aromatic heterocycle. Here, an aromatic heterocycle is a monovalent group of an aromatic ring or a derivative of an aromatic ring, and means a group containing one or more of N, O, S, and Si in a heteroatom. The derivative of the aromatic ring includes all structures in which an aromatic ring or an aliphatic ring is condensed on the aromatic ring. In addition, in the present specification, the heteroaryl group is intended to include a monovalent group in which an aromatic ring containing two or more heteroatoms or a derivative of an aromatic ring containing heteroatoms is connected to each other. 2 to 50 carbon atoms of the heteroaryl group; 2 to 30; 2 to 20; 2 to 18; Or it is preferably 2 to 13.

Examples of the heteroaryl group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, and acry Din group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, phthalazine, pteridine group, pyridoopyrimidine, pyridopyrimidine, pyridopyrazine, Pyrazinopyrazine, isoquinoline, indole, pyridodoindole, indopyrimidine (5H-indenopyrimidine), carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole Sol group, benzothiophene group, dibenzothiophene group, benzofuran group, dibenzofuran group, dibenzosilole group, phenanthroline group, thiazolyl group, isooxazolyl group, oxadiazolyl group And thiadiazolyl groups, but are not limited thereto.

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

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. These may be applied to the description of the heteroaryl group described above, except that each is a divalent group.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. Can be. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the cycloalkyl group or aryl group except for the non-monovalent. Examples of aromatic and aliphatic condensed rings include, but are not limited to, 1,2,3,4-tetrahydronaphthalene group, 2,3-dihydro-1H-indene group, and the like.

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 is a non-carbon atom, and contains one or more heteroatoms. Specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, S and Si. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the heteroaryl group except that it is not monovalent.

In the formulas (1) and (2) herein, the substituted substituents include those substituted with deuterium even when not specified.

Hereinafter, an organic light emitting device according to an exemplary embodiment of the present specification and a compound included therein will be described.

This specification is an anode; cathode; An organic light-emitting device including a first organic material layer and a second organic material layer provided between the anode and the cathode, wherein the first organic material layer includes a compound represented by Chemical Formula 1, and the second organic material layer is represented by Chemical Formula 2 It provides an organic light emitting device comprising a compound to be.

The compound represented by Chemical Formula 1 according to an exemplary embodiment includes boron (B) and two nitrogens at the center. Due to the introduction of the boron compound, it is possible to minimize orbital overlap between HOMO (highest occupied molecular orbital) and LUMO (lowest occupied molecular orbital), thereby maintaining high triplet energy while maintaining a wide band gap. Due to this, high efficiency of the device can be expected.

The compound represented by Chemical Formula 2 has a structure in which a hetero ring containing 1 or more N is connected to a spiro type ring containing O or S. Due to the spiro-type ring containing O or S, a steric hindrance occurs in the compound. The steric hindrance prevents crystallization during film formation and increases thermal stability, so that the layer can be stably formed even at a high deposition temperature. In an exemplary embodiment, when the compound represented by Chemical Formula 2 is used in an organic material layer, an effect of increasing the life of the device can be expected due to high thermal stability and fairness. In addition, high efficiency of the device can be expected by having a heterocycle containing 1 or more N as a substituent.

In the compound represented by Formula 2, it is not a symmetrical structure (ie, R21 and R22; or R23 and R24 at the same time include the structure of Formula 3). That is, the structure of Chemical Formula 3 is asymmetrically included. In this case, due to the asymmetric structure of Formula 2, the dipole moment of the molecule is improved. Accordingly, when the compound represented by Chemical Formula 2 is included in the organic material layer (eg, an electron transport layer) between the cathode and the light emitting layer, the electron injection rate into the light emitting layer is increased, thereby lowering the driving voltage of the organic light emitting device. In addition, due to the asymmetric structure, the crystallinity in the solution state is lowered, and an economical effect can be expected in terms of time and/or cost when forming the organic material layer.

The value of the dipole moment of the compound represented by Chemical Formula 2 according to an exemplary embodiment of the present specification is 0.6 debye or more. The value of the dipole moment may be due to structural features.

In this specification, the dipole moment (dipole moment) is a physical quantity indicating the degree of polarity, it can be calculated by the following equation (1).

[Equation 1]

In Equation 1, the molecular density can be obtained by calculation, and a dipole moment value can be obtained. For example, molecular density can be obtained by calculating the charge and dipole for each atom using a method called Hirshfeld Charge Analysis and calculating according to the following equation.

As described above, the compound of Formula 2 is an excellent material having an excellent electron injection effect due to its asymmetric structure. Therefore, it is desirable to maintain the hole-electron balance in the light emitting layer. The compound represented by Chemical Formula 1 has high LUMO energy. (In other words, the absolute value is small) When the compound of Formula 1 is used as a dopant in the light emitting layer, electrons transferred from the compound of Formula 2 are not transferred to the compound of Formula 1, but are mostly transferred to the host of the light emitting layer to improve stability. Therefore, the efficiency and life of the organic light emitting device including the compound of Formula 1 and the compound of Formula 2 are excellent.

In one embodiment of the present specification, X is B; P=O; Or P=S.

In one embodiment of the present specification, X is B.

In one embodiment of the present specification, Z1 to Z3 are the same as or different from each other, and each independently a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In one embodiment of the present specification, Z1 to Z3 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C20 hydrocarbon ring; Or a substituted or unsubstituted C2-C20 heterocycle.

In one embodiment of the present specification, Z1 to Z3 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tricyclic hydrocarbon ring; Or a substituted or unsubstituted monocyclic to tricyclic heterocycle.

In one embodiment of the present specification, Z1 to Z3 are the same as or different from each other, and each independently substituted or unsubstituted benzene ring; A substituted or unsubstituted naphthalene ring; A substituted or unsubstituted fluorene ring; A substituted or unsubstituted carbazole ring; Substituted or unsubstituted dibenzofuran ring; A substituted or unsubstituted dibenzothiophene ring; Or a substituted or unsubstituted dibenzo selenophene ring.

In one embodiment of the present specification, Z1 to Z3 are the same as or different from each other, and each independently substituted or unsubstituted benzene ring; A substituted or unsubstituted naphthalene ring; A substituted or unsubstituted carbazole ring; Substituted or unsubstituted dibenzofuran ring; Or a substituted or unsubstituted dibenzothiophene ring.

In one embodiment of the present specification, Z1 is a hydrocarbon ring unsubstituted or substituted with R1; Or a heterocycle substituted or unsubstituted with R1.

In one embodiment of the present specification, Z2 is a hydrocarbon ring unsubstituted or substituted with R2; Or a heterocycle substituted or unsubstituted with R2.

In one embodiment of the present specification, Z3 is a hydrocarbon ring substituted or unsubstituted with R3; Or a heterocycle substituted or unsubstituted with R3.

In one embodiment of the present specification, Z1 is a benzene ring substituted or unsubstituted with R1; A naphthalene ring unsubstituted or substituted with R1; A carbazole ring unsubstituted or substituted with R1; Dibenzofuran ring unsubstituted or substituted with R1; Or a dibenzothiophene ring unsubstituted or substituted with R1.

In one embodiment of the present specification, Z2 is a benzene ring substituted or unsubstituted with R2; A naphthalene ring unsubstituted or substituted with R1; A carbazole ring unsubstituted or substituted with R2; Dibenzofuran ring unsubstituted or substituted with R2; Or a dibenzothiophene ring unsubstituted or substituted with R2.

In one embodiment of the present specification, Z3 is a benzene ring substituted or unsubstituted with R3.

In one embodiment of the present specification, at least one of Z1 and Z2 is a substituted or unsubstituted aromatic hydrocarbon ring. It is preferably a substituted or unsubstituted benzene ring.

In one embodiment of the present specification, Z1 is an aromatic hydrocarbon ring unsubstituted or substituted with R1, and Z2 is an aromatic hydrocarbon ring unsubstituted or substituted with R2.

In one embodiment of the present specification, Z1 is a hydrocarbon ring substituted or unsubstituted with R1, and Z2 is an aromatic heterocycle substituted or unsubstituted with R2.

In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C1-C10 haloalkyl group; A substituted or unsubstituted C3-C10 cycloalkyl group; A substituted or unsubstituted C1-C30 silyl group; A substituted or unsubstituted C1-C10 alkoxy group; A substituted or unsubstituted C1-C10 amine group; A substituted or unsubstituted C6-C60 arylamine group; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; C1-C10 alkyl group; C1-C10Alkoxy group; C1-C10 amine group; C6-C60 arylamine group; C6-C30Aryl group; And one or more substituents selected from the group consisting of C2-C30 heterocyclic groups.

In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C1-C10 alkyl group; C1-C10 alkyl group or C6-C60 arylamine group substituted or unsubstituted C6-C60 arylamine group; C6-C30Aryl group; Or it is a C2-C30 heterocyclic group.

In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C1-C6 alkyl group; A C6-C60 arylamine group unsubstituted or substituted with a C1-C10 alkyl group; C6-C30Aryl group; Or it is a C2-C30 heterocyclic group. In another exemplary embodiment, the heterocyclic group of R1 to R3 may be an N-containing heterocyclic group, specifically, a carbazole group.

In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently a methyl group; Ethyl group; tert-butyl group; Phenyl group; Biphenyl group; A diphenylamine group substituted or unsubstituted with a diphenylamine group, a ditolylamine group (di-tolylamine), or a bis((tert-butyl)phenyl)amine group; Or carbazole.

In one embodiment of the present specification, two adjacent R1s combine with each other to form a substituted or unsubstituted monocyclic or bicyclic aromatic hydrocarbon ring.

In one embodiment of the present specification, two adjacent R2s combine with each other to form a substituted or unsubstituted monocyclic or bicyclic aromatic hydrocarbon ring.

In one embodiment of the present specification, two adjacent R1s combine with each other to form a substituted or unsubstituted benzene ring with an alkyl group of C1-C10.

In one embodiment of the present specification, two adjacent R2s combine with each other to form a substituted or unsubstituted benzene ring with an alkyl group of C1-C10.

In one embodiment of the present specification, R3 is hydrogen; heavy hydrogen; C1-C10 alkyl group; C6-C60 arylamine group; And one or more substituents selected from the group consisting of C2-C30 heterocyclic groups.

In one embodiment of the present specification, R3 is hydrogen; heavy hydrogen; C1-C10 alkyl group; A C6-C60 arylamine group unsubstituted or substituted with a C1-C10 alkyl group; Or it is a C2-C30 heterocyclic group.

In one embodiment of the present specification, R3 is hydrogen; heavy hydrogen; C1-C10 alkyl group; C6-C60 arylamine group; Or it is a C2-C30 heterocyclic group.

In one embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Methyl group; Ethyl group; tert-butyl group; a diphenylamine group unsubstituted or substituted with tertbutyl group; Or carbazole.

In one embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Methyl group; Diphenylamine group; Or carbazole.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C1-C10 alkyl group; C6-C60 arylamine group; C6-C30Aryl group; And a C2-C30 heterocyclic group, or a substituent selected from the group consisting of two or more substituents.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C1-C10 alkyl group; C1-C10 alkyl group or C6-C60 arylamine group substituted or unsubstituted C6-C60 arylamine group; C6-C30Aryl group; Or it is a C2-C30 heterocyclic group. In another exemplary embodiment, the heterocyclic group of R1 and R3 may be an N-containing heterocyclic group, specifically, a carbazole group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it is a C1-C10 alkyl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it is a C1-C6 alkyl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a methyl group; Ethyl group; tert-butyl group; Phenyl group; Biphenyl group; Or a diphenylamine group unsubstituted or substituted with a diphenylamine group, a methyl group, or a tert-butyl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a methyl group; Ethyl group; Or tert-butyl group.

In one embodiment of the present specification, A1 is N(R101) or O.

In one embodiment of the present specification, A2 is N(R102) or O.

In one embodiment of the present specification, A1 is N(R101).

In one embodiment of the present specification, A2 is N(R102).

In one embodiment of the present specification, A1 is O.

In one embodiment of the present specification, A2 is O.

In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently an substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted C6-C30 aryl group.

In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently a C1-C10 alkyl group; Or a C6-C30 aryl group unsubstituted or substituted with a C1-C10 alkyl group.

In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently a methyl group; tert-butyl group; A phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group; Or a biphenyl group unsubstituted or substituted with tert-butyl group.

In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 101 to 108.

[Formula 101]

[Formula 102]

[Formula 103]

[Formula 104]

[Formula 105]

[Formula 106]

[Formula 107]

[Formula 108]

In the formulas 101 to 108,

The definitions of X, A1 and A2 are as defined in Formula 1,

Q is O; S; Se; N(R51); Or C(R52)(R53),

R11 to R20 and R51 to R53 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

r11 and r12 are integers from 0 to 4, and when 2 or more, R11 and R12 are the same as or different from each other,

r13 is an integer from 0 to 3, and when 2 or more, R13 is the same or different from each other,

r14 to r20 are integers from 0 to 6, and when 2 or more, R14 to R20 are the same or different from each other.

In one embodiment of the present specification, the definition of R1 described above may be applied to R11. In another exemplary embodiment, the above-described definition of R2 may be applied to R12, R14 to R20. In another exemplary embodiment, the above definition of R3 may be applied to R13.

In one embodiment of the present specification, Q is O; S; Or N(R51).

In one embodiment of the present specification, Q is O; Or S.

In one embodiment of the present specification, R51 is a substituted or unsubstituted C6-C30 aryl group.

In one embodiment of the present specification, R51 is a C6-C20 aryl group.

In one embodiment of the present specification, R51 is a phenyl group.

In one embodiment of the present specification, R52 and R53 are the same as or different from each other, and each independently a methyl group; Or a phenyl group.

In one embodiment of the present specification, R11 to R20 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R11 to R20 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C1-C10 alkyl group; C1-C10 alkyl group or C6-C60 arylamine group substituted or unsubstituted C6-C60 arylamine group; C6-C30Aryl group; Or it is a C2-C30 heterocyclic group.

In one embodiment of the present specification, R11 to R20 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C1-C6 alkyl group; A C6-C60 arylamine group unsubstituted or substituted with a C1-C10 alkyl group; C6-C30Aryl group; Or it is a C2-C30 heterocyclic group. In another exemplary embodiment, the heterocyclic group of R11 to R20 may be an N-containing heterocyclic group, specifically, a carbazole group.

In one embodiment of the present specification, R11 to R20 are the same as or different from each other, and each independently a methyl group; Ethyl group; tert-butyl group; Phenyl group; Biphenyl group; A diphenylamine group substituted or unsubstituted with a diphenylamine group, a ditolylamine group (di-tolylamine), or a bis((tert-butyl)phenyl)amine group; Or carbazole.

In one embodiment of the present specification, R13 is hydrogen; heavy hydrogen; C1-C10 alkyl group; C6-C60 arylamine group; And one or more substituents selected from the group consisting of C2-C30 heterocyclic groups.

In one embodiment of the present specification, R13 is hydrogen; heavy hydrogen; C1-C10 alkyl group; A C6-C60 arylamine group unsubstituted or substituted with a C1-C10 alkyl group; Or it is a C2-C30 heterocyclic group.

In one embodiment of the present specification, R13 is hydrogen; heavy hydrogen; C1-C10 alkyl group; C6-C60 arylamine group; Or it is a C2-C30 heterocyclic group.

In one embodiment of the present specification, R13 is hydrogen; heavy hydrogen; Methyl group; Ethyl group; tert-butyl group; a diphenylamine group unsubstituted or substituted with tertbutyl group; Or carbazole.

In one embodiment of the present specification, R13 is hydrogen; heavy hydrogen; Methyl group; Diphenylamine group; Or carbazole.

In one embodiment of the present specification, R11, R12, R14 to R20 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C1-C10 alkyl group; C6-C60 arylamine group; C6-C30Aryl group; And a C2-C30 heterocyclic group, or a substituent selected from the group consisting of two or more substituents.

In one embodiment of the present specification, R11, R12, R14 to R20 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C1-C10 alkyl group; C1-C10 alkyl group or C6-C60 arylamine group substituted or unsubstituted C6-C60 arylamine group; C6-C30Aryl group; Or it is a C2-C30 heterocyclic group. In another exemplary embodiment, the heterocyclic groups of R11, R12, and R14 to R20 may be N-containing heterocyclic groups, specifically carbazole groups.

In one embodiment of the present specification, R11, R12, R14 to R20 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it is a C1-C10 alkyl group.

In one embodiment of the present specification, R11, R12, R14 to R20 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it is a C1-C6 alkyl group.

In one embodiment of the present specification, R11, R12, R14 to R20 are the same as or different from each other, and each independently a methyl group; Ethyl group; tert-butyl group; Phenyl group; Biphenyl group; Or a diphenylamine group unsubstituted or substituted with a diphenylamine group, a methyl group, or a tert-butyl group.

In one embodiment of the present specification, R11, R12, R14 to R20 are the same as or different from each other, and each independently a methyl group; Ethyl group; Or tert-butyl group.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is any one selected from the following compounds.

In one embodiment of the present specification, Y is O; Or S.

In one embodiment of the present specification, Y is O.

In one embodiment of the present specification, Y is S.

In one embodiment of the present specification, R21 to R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, represented by the formula (3), or adjacent substituents combine with each other to form a substituted or unsubstituted ring, at least one of R21 to R24 is represented by the formula (3).

In one embodiment of the present specification, R21 is represented by Chemical Formula 3.

In one embodiment of the present specification, R22 is represented by Chemical Formula 3.

In one embodiment of the present specification, R23 is represented by Chemical Formula 3.

In one embodiment of the present specification, R24 is represented by Chemical Formula 3.

In one embodiment of the present specification, R21 to R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C6-C30 heterocyclic group, represented by the formula (3), or adjacent substituents combine with each other to form a substituted or unsubstituted C3-C30 ring.

In one embodiment of the present specification, R21 to R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C1-C10 alkyl group; Or a C6-C30 aryl group unsubstituted or substituted with a C1-C10 alkyl group, or represented by Chemical Formula 3, or adjacent substituents combine with each other to form a benzene ring.

In one embodiment of the present specification, R21 to R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; Propyl group; Isopropyl group; n-butyl group; sec-butyl group; tert-butyl group; A phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group; Biphenyl group; Or a naphthyl group, represented by Chemical Formula 3, or adjacent substituents combine with each other to form a benzene ring.

In one embodiment of the present specification, at least one of R21 to R24 is represented by Chemical Formula 3, and the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C6-C30 heterocyclic group, or two of adjacent R21, two of adjacent R22, two of adjacent R23, or two of adjacent R24 is bonded to each other to be substituted or unsubstituted C3-C30 To form a ring.

In one embodiment of the present specification, one or two of R21 to R24 is represented by Chemical Formula 3, and the other is the same or different from each other, and each independently hydrogen; heavy hydrogen; C1-C10 alkyl group; Or a C6-C30 aryl group unsubstituted or substituted with a C1-C10 alkyl group, or two of the adjacent R21, two of the adjacent R22, two of the adjacent R23, or two of the adjacent R24 combine with each other to form a benzene ring. To form.

In one embodiment of the present specification, one or two of R21 to R24 is represented by Chemical Formula 3, and the other is the same or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; Propyl group; Isopropyl group; n-butyl group; sec-butyl group; tert-butyl group; A phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group; Biphenyl group; Or a naphthyl group, two of the adjacent R21, two of the adjacent R22, two of the adjacent R23, or two of the adjacent R24 combine with each other to form a benzene ring.

In one embodiment of the present specification, one or two of R21 to R24 is represented by Chemical Formula 3, and the other is the same or different from each other, and each independently hydrogen; heavy hydrogen; Or a phenyl group unsubstituted or substituted with a methyl group, or two of the adjacent R21 or two of the adjacent R22 combine with each other to form a benzene ring.

In one embodiment of the present specification, two adjacent R21s combine with each other to form a substituted or unsubstituted benzene ring.

In one embodiment of the present specification, two adjacent R22s combine with each other to form a substituted or unsubstituted benzene ring.

In one embodiment of the present specification, two adjacent R21s combine with each other to form a benzene ring.

In one embodiment of the present specification, two adjacent R22s combine with each other to form a benzene ring.

In one embodiment of the present specification, r21 to r24 are the same or different from each other, and each independently an integer of 0 to 4, and when r21 is 2 or more, R21 is the same or different from each other, and when r22 is 2 or more, R22 is R23 is the same or different from each other when R23 is 2 or more, and R24 is the same or different from each other when r24 is 2 or more.

In one embodiment of the present specification, the r21 to r24 are the same as or different from each other, and each independently 0 to 2.

In one embodiment of the present specification, X1 is N or C(R31).

In one embodiment of the present specification, X2 is N or C(R32).

In one embodiment of the present specification, X3 is N or C(R33).

In one embodiment of the present specification, at least one of X1 to X3 is N.

In one embodiment of the present specification, two or more of X1 to X3 are N.

In one embodiment of the present specification, X1 to X3 are all N.

In one embodiment of the present specification, X1 is N, X2 is N, and X3 is C(R33). In another exemplary embodiment, R33 is combined with Ar2 to form a benzene ring.

In one embodiment of the present specification, X1 is N, X2 is C(R32), and X3 is N. In another exemplary embodiment, R33 is combined with Ar2 to form a benzene ring.

In one embodiment of the present specification, R31, R32, and R33 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted aromatic hydrocarbon ring in combination with Ar1 or Ar2; Or a substituted or unsubstituted heterocycle.

In one embodiment of the present specification, R31, R32, and R33 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heterocyclic group, or a C6-C30 aromatic hydrocarbon ring substituted or unsubstituted with Ar1 or Ar2; Or a substituted or unsubstituted C2-C30 heterocycle. In another exemplary embodiment, “substituted or unsubstituted” is one substituent selected from the group consisting of deuterium, a C1-C10 alkyl group, a C6-C30 aryl group, and a C2-C30 heteroaryl group, or two or more substituents Refers to a substituent with or without any substituent.

In one embodiment of the present specification, R31, R32, and R33 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted monocyclic to 4 ring aryl group; Or a substituted or unsubstituted monocyclic to 4 ring heterocyclic group, or by combining with Ar1 or Ar2 substituted or unsubstituted monocyclic to 4 ring aromatic hydrocarbon ring; Or form a substituted or unsubstituted monocyclic to 4 ring heterocycle. In another exemplary embodiment, “substituted or unsubstituted” is one substituent selected from the group consisting of deuterium, a C1-C10 alkyl group, a C6-C30 aryl group, and a C2-C30 heteroaryl group, or two or more substituents Refers to a substituent with or without any substituent.

In one embodiment of the present specification, R31, R32, and R33 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Phenyl group; Biphenyl group; Naphthyl group; Carbazole; Phenyl carbazole group; Or it is a benzocarbazole group, or combines with Ar1 or Ar2 to form a substituted or unsubstituted benzene ring with a C6-C30 aryl group or a C2-C30 heterocyclic group.

In one embodiment of the present specification, R31, R32, and R33 are each hydrogen or deuterium.

In one embodiment of the present specification, R31, R32, and R33 are hydrogen.

In one embodiment of the present specification, R31 is a substituted or unsubstituted ring in combination with Ar1; A substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In one embodiment of the present specification, R32 is a substituted or unsubstituted ring in combination with Ar1; A substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In one embodiment of the present specification, R32 is a substituted or unsubstituted ring in combination with Ar2; A substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In one embodiment of the present specification, R33 is a substituted or unsubstituted ring in combination with Ar2; A substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In one embodiment of the present specification, R31 is combined with Ar1 to form a substituted or unsubstituted benzene ring with R41.

In one embodiment of the present specification, R32 is combined with Ar1 to form a benzene ring substituted or unsubstituted with R41.

In one embodiment of the present specification, R32 is combined with Ar2 to form a substituted or unsubstituted benzene ring with R41.

In one embodiment of the present specification, R33 is combined with Ar2 to form a substituted or unsubstituted benzene ring with R41.

In one 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; Or a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted aromatic hydrocarbon ring in combination with R31, R32 or R33; Or a substituted or unsubstituted heterocycle.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently is a group consisting of deuterium, cyano group, C1-C10 alkyl group, C6-C30 aryl group, and C2-C20 heterocyclic group. C6-C30 aryl group unsubstituted or substituted with a substituent linked to one or more substituents selected from the group or selected from the group; Or C6-substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, cyano, C1-C10 alkyl, C6-C30 aryl and C2-C20 heterocyclic groups It is a heterocyclic group of C30.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently selected from the group consisting of deuterium, cyano group, C6-C30 aryl group, and C2-C20 heterocyclic group or the group. A C6-C30 aryl group unsubstituted or substituted with a substituent linked by at least two substituents; Or a C6-C30 heterocyclic group unsubstituted or substituted with a deuterium, a C6-C30 aryl group, or a C2-C20 heterocyclic group, or a substituent group of two or more substituents selected from the group.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently selected from the group consisting of deuterium, cyano group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, and carbazole group. It is a C6-C20 aryl group which is unsubstituted or substituted with a substituent linked by one or more substituents selected from the above group.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently an aryl group substituted or unsubstituted with R41; Or a heterocyclic group unsubstituted or substituted with R42, or an aromatic hydrocarbon ring unsubstituted or substituted with R41 in combination with R31, R32 or R33; Or a heterocycle substituted or unsubstituted with R42.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group; Or a C2-C30 heterocyclic group unsubstituted or substituted with R42, or a C6-C30 aromatic hydrocarbon ring substituted or unsubstituted with R41 in combination with R31, R32 or R33; Or C2-C30 substituted or unsubstituted with R42.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C20 aryl group with R41; Or a C2-C20 heterocyclic group unsubstituted or substituted with R42, or a C6-C20 aromatic hydrocarbon ring unsubstituted or substituted with R41 in combination with R31, R32 or R33; Or C2-C20 substituted or unsubstituted with R42.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 5-cyclic aryl group with R41; Or a monocyclic to 5 ring heterocyclic group unsubstituted or substituted with R42, or a monocyclic to 5 ring aromatic hydrocarbon ring substituted or unsubstituted with R41 in combination with R31, R32 or R33; Or a monocyclic to 5 ring heterocycle substituted or unsubstituted with R42.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a monocyclic to 4 ring aryl group substituted or unsubstituted with R41; Or a monocyclic to 4 ring heterocyclic group unsubstituted or substituted with R42, or a monocyclic to 4 ring aromatic hydrocarbon ring substituted or unsubstituted with R41 in combination with R31, R32 or R33; Or it forms a monocyclic to 4 ring heterocycle substituted or unsubstituted with R42.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently a monocyclic to tricyclic aryl group substituted or unsubstituted with R41; Or a monocyclic to tricyclic heterocyclic group substituted or unsubstituted with R42, or a monocyclic to tricyclic aromatic hydrocarbon ring substituted or unsubstituted with R41 in combination with R31, R32 or R33; Or a monocyclic to tricyclic heterocycle substituted or unsubstituted with R42.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrenyl group; Triphenylene group; Fluoranthenyl group; Phenylene group; Anthracenyl group; Fluorenyl group; Or a dimethyl fluorenyl group, the substituent is substituted or unsubstituted with R41.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently substituted or unsubstituted with R42, and are a monocyclic to 5-cyclic heterocyclic group containing N, O, S, or Si. .

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a carbazole group; Phenyl carbazole group; Benzocarbazole group; Indenocarbazole; Dibenzothiophene group; Dibenzofuran group; Dibenzosilole group (dibenzosilole); Phenox camera; Phenothiazine group; Phenazine group; Acridine group; Dihydrophenazine group; Dihydroacridine group; Pyridyl group; Pyrimidyl group; Quinoline group; Isoquinoline group; Quinazoline groups; Pyridopyrimidine group; Pyridopyrazine group; Pyrimidoindole; Or a pyridoindole group, the substituent is substituted or unsubstituted with R42.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted ring in combination with R31; A substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted ring in combination with R32; A substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted ring in combination with R32; A substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted ring in combination with R33; A substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In one embodiment of the present specification, Ar1 is combined with R31 to form a substituted or unsubstituted benzene ring with R41.

In one embodiment of the present specification, Ar1 is combined with R32 to form a substituted or unsubstituted benzene ring with R41.

In one embodiment of the present specification, Ar2 is combined with R32 to form a substituted or unsubstituted benzene ring with R41.

In one embodiment of the present specification, Ar2 is combined with R33 to form a substituted or unsubstituted benzene ring with R41.

In one embodiment of the present specification, R41 and R42 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; Alkyl groups; Haloalkyl group; Alkoxy groups; Silyl group; Aryl group; And a heterocyclic group, or two or more substituents.

In one embodiment of the present specification, R41 and R42 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; C1-C20 alkyl group; C1-C20 haloalkyl group; C1-C20Alkoxy group; C1-C50 silyl group; C6-C50 aryl group; And C2-C50 heterocyclic group, or two or more substituents.

In one embodiment of the present specification, R41 and R42 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; C1-C10 alkyl group; C1-C10 haloalkyl group; C1-C10Alkoxy group; C1-C30 silyl group; C6-C30Aryl group; And C2-C30 heterocyclic group, or two or more substituents.

In one embodiment of the present specification, R41 and R42 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; C1-C5 alkyl group; C1-C5 haloalkyl group; C1-C5 alkoxy group; C1-C20 silyl group; C6-C20Aryl group; And C2-C20 heterocyclic group, or two or more substituents.

In one embodiment of the present specification, R41 and R42 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; C1-C20 alkyl group; C1-C20 haloalkyl group; C1-C20Alkoxy group; C1-C50 silyl group; Monocyclic to 5 ring aryl groups; And a monocyclic to 5 ring heterocyclic group, or two or more substituents.

In one embodiment of the present specification, R41 and R42 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; C1-C10 alkyl group; C1-C10 haloalkyl group; C1-C10Alkoxy group; C1-C30 silyl group; Monocyclic to 4 ring aryl groups; And it is one selected from the group consisting of a monocyclic to 4 ring heterocyclic group, or two or more substituents are connected.

In one embodiment of the present specification, R41 and R42 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; C1-C5 alkyl group; C1-C5 haloalkyl group; C1-C5 alkoxy group; C1-C20 silyl group; Monocyclic to tricyclic aryl groups; And a monocyclic to tricyclic heterocyclic group, or two or more substituents.

In one embodiment of the present specification, R41 and R42 are the same as or different from each other, and each independently deuterium; Nitrile group; Methyl group; Ethyl group; Propyl group; Isopropyl group; n-butyl group; tert-butyl group; Trifluoromethyl group; Methoxy group; Ethoxy group; Trimethylsilyl group; Triphenylsilyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrenyl group; Triphenylene group; Fluoranthenyl group; Phenylene group; Anthracenyl group; Fluorenyl group; Dimethylfluorenyl group; Carbazole; Phenyl carbazole group; Benzocarbazole group; Indenocarbazole; Dibenzothiophene group; Dibenzofuran group; Dibenzosilole group (dibenzosilole); Phenox camera; Phenothiazine group; Phenazine group; Acridine group; Dihydrophenazine group; Dihydroacridine group; Pyridyl group; Pyrimidyl group; Quinoline group; Isoquinoline group; Quinazoline groups; Pyridopyrimidine group; Pyridopyrazine group; Pyrimidoindole; And pyridoindole groups, or two or more substituents.

In one embodiment of the present specification, L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.

In one embodiment of the present specification, L is a direct bond; A substituted or unsubstituted C6-C30 arylene group; Or a substituted or unsubstituted C2-C30 divalent heterocyclic group.

In one embodiment of the present specification, L is a direct bond; C6-C30arylene group; Or a C2-C30 divalent heterocyclic group. The arylene group or divalent heterocyclic group is a nitrile group; C1-C10 alkyl group; C6-C30Aryl group; And one or more substituents selected from the group consisting of C2-C30 heterocyclic groups or substituted or unsubstituted substituents.

In one embodiment of the present specification, L is a direct bond; Monocyclic to 5 ring arylene groups; Or it is a monocyclic to 5 ring bivalent heterocyclic group. The arylene group or divalent heterocyclic group is a nitrile group; C1-C10 alkyl group; C6-C30Aryl group; And one or more substituents selected from the group consisting of C2-C30 heterocyclic groups or substituted or unsubstituted substituents.

In one embodiment of the present specification, L is a direct bond; Monocyclic to 4 ring arylene groups; Or a monocyclic to 4 ring divalent heterocyclic group. The arylene group or divalent heterocyclic group is a nitrile group; C1-C10 alkyl group; C6-C30Aryl group; And one or more substituents selected from the group consisting of C2-C30 heterocyclic groups or substituted or unsubstituted substituents.

In one embodiment of the present specification, L is a direct bond; Phenylene group; Biphenylene group; Terphenylene group; Naphthylene group; Anthracenyl group; A divalent phenanthrenyl group; Divalent triphenylene group; A divalent fluoranthenyl group; Divalent phenylene group; A divalent fluorenyl group; A divalent dimethylfluorenyl group; Divalent carbazole group; Divalent phenylcarbazole group; Divalent benzocarbazole group; Divalent indenocarbazole; Divalent dibenzothiophene group; Divalent dibenzofuran group; Divalent dibenzocyrol group; A divalent phenoxy camera; Divalent phenothiazine group; Divalent phenazine group; A divalent acridine group; Divalent dihydrophenazine group; A divalent dihydroacridine group; Divalent pyridyl group; Divalent pyrimidyl group; Divalent quinoline group; A divalent isoquinoline group; A divalent quinazoline group; A divalent pyridopyrimidine group; Divalent pyridopyrazine group; Divalent pyrimidoindole; Or a divalent pyridoindol group. The linking group (L) is a nitrile group; C1-C10 alkyl group; C6-C30Aryl group; And one or more substituents selected from the group consisting of C2-C30 heterocyclic groups or substituted or unsubstituted substituents.

In one embodiment of the present specification, L is a direct bond; C6-C30arylene group; Or a C2-C30 divalent heterocyclic group.

In one embodiment of the present specification, L is a direct bond; C6-C30arylene group; Or a C2-C30 divalent N-containing heterocyclic group.

In one embodiment of the present specification, L is a direct bond; Phenylene group; Biphenylene group; Terphenylene group; Naphthylene group; Divalent dibenzothiophene group; Divalent dibenzofuran group; Divalent pyridyl group; Divalent pyrimidyl group; Divalent quinoline group; Or a divalent isoquinoline group.

In one embodiment of the present specification, L is a direct bond; Phenylene group; Divalent pyridyl group; Or a divalent dibenzothiophene group.

In one embodiment of the present specification, L is a direct bond; Phenylene group; Biphenylene group; Or a naphthylene group.

In one embodiment of the present specification, L is a direct bond.

In one embodiment of the present specification, m is an integer from 0 to 2.

In one embodiment of the present specification, m is 0 or 1.

In one embodiment of the present specification, m is 0.

In one embodiment of the present specification, r21 is an integer from 0 to 2.

In one embodiment of the present specification, r22 is an integer from 0 to 2.

In one embodiment of the present specification, r23 is an integer from 0 to 2.

In one embodiment of the present specification, r24 is an integer from 0 to 2.

In one embodiment of the present specification, r21 is 1.

In one embodiment of the present specification, r22 is 1.

In one embodiment of the present specification, r23 is 1.

In one embodiment of the present specification, r24 is 1.

In one embodiment of the present specification, Chemical Formula 3 is represented by any one of the following Chemical Formulas 301 to 303.

[Chemical Formula 301]

[Chemical Formula 302]

[Formula 303]

In the above formulas 301 to 303,

L, m, Ar1 and Ar2 are defined as in Chemical Formula 3,

At least one of X1 to X3 is N, the other is CH or CD,

R30 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r30 is an integer from 0 to 4, and when r30 is 2 or more, R30 is the same or different from each other.

In one embodiment of the present specification, in Chemical Formula 301, X1 is N or C(R31), X2 is N or C(R32), X3 is N or C(R33), and one of X1 to X3 Above is N, R31, R32 and R33 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, in Chemical Formula 301, R31, R32, and R33 are hydrogen.

In one embodiment of the present specification, R30 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-10 alkyl group; Or a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heterocyclic group.

In one embodiment of the present specification, R30 is hydrogen; Methyl group; Phenyl group; Or a benzocarbazole group.

In one embodiment of the present specification, R30 is hydrogen.

In one embodiment of the present specification, Chemical Formula 2 is represented by any one of the following Chemical Formulas 201 to 204.

[Formula 201]

[Formula 202]

[Formula 203]

[Formula 204]

In Chemical Formulas 201 to 204,

X1 to X3, L, m, Ar1, Ar2, R21 to R24, r21 to r24 and Y are the same as defined in Formula 2,

X4 is N or C(R34), X5 is N or C(R35), X6 is N or C(R36), and one or more of X4 to X6 is N,

R34, R35 and R36 are the same as or different from each other, and each independently hydrogen; Or deuterium, or a substituted or unsubstituted aromatic hydrocarbon ring in combination with Ar3 or Ar4; Or form a substituted or unsubstituted heteroring,

Ar3 and Ar4 are the same as or different from each other, and each independently an aryl group substituted or unsubstituted with R43; Or a heterocyclic group unsubstituted or substituted with R44, or an aromatic hydrocarbon ring substituted or unsubstituted with R34, R35 or R36; Or form a substituted or unsubstituted heteroring,

R43 and R44 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; Alkyl groups; Haloalkyl group; Alkoxy groups; Silyl group; Aryl group; And a heterocyclic group, or two or more substituents are connected,

L11 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

m11 is an integer of 0-4, and when it is 2 or more, L11 is the same or different from each other.

In one embodiment of the present specification, the formulas 201 to 204

And

May be represented by any one of the above formulas 301 to 303.

In one embodiment of the present specification, the description of L described above may be applied to L11.

In one embodiment of the present specification, the description of m described above may be applied to m11.

In one embodiment of the present specification, the descriptions of X1 to X3 described above may be applied to X4 to X6.

In one embodiment of the present specification, the descriptions of Ar1 and Ar2 described above may be applied to Ar3 and Ar4.

According to an exemplary embodiment of the present specification, the formula 2 is represented by any one of the following formulas 211 to 218.

[Formula 211]

[Formula 212]

[Formula 213]

[Formula 214]

[Formula 215]

[Formula 216]

[Formula 217]

[Formula 218]

In the formulas 211 to 218,

The definitions of X1 to X3, L, m, Ar1, Ar2, R21 to R24, r21 to r24 and Y are as defined in Formula 2.

According to an exemplary embodiment of the present specification, the formula 2 is represented by any one of the following formulas 401 to 403.

[Formula 401]

[Formula 402]

[Formula 403]

In the above formulas 401 to 403,

X1 to X3, L, m, Ar1, Ar2, R21, R22, R24, r21, r22, r24 and Y are the same as defined in Formula 2,

R25 and R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r25 and r26 are the same or different from each other, and each independently an integer of 0 to 6, and when r25 is 2 or more, R25 is the same or different from each other, and when r26 is 2 or more, R26 is the same or different from each other.

In one embodiment of the present specification, the descriptions of R21 and R22 described above may be applied to R25 and R26.

According to an exemplary embodiment of the present specification, the compound represented by Formula 2 is any one selected from the following compounds.

This specification is an anode; cathode; An organic light emitting device including a first organic material layer and a second organic material layer provided between the anode and the cathode, wherein the first organic material layer includes a compound represented by Chemical Formula 1, and the second organic material layer is represented by Chemical Formula 2 It provides an organic light emitting device comprising a compound to be.

The organic light emitting device according to the present specification may include an additional organic material layer in addition to the first organic material layer and the second organic material layer.

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

In the present specification, the'layer' is a meaning compatible with the'film' mainly used in the technical field, and refers to a coating covering a desired area. The size of the'layer' is not limited, and each'layer' may have the same or different sizes. In an exemplary embodiment, the size of the'layer' may be the same as that of the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.

In the present specification, the meaning that a specific A material is included in the B layer means i) one or more A materials are included in one B layer, and ii) the B layer is composed of one or more layers, and the A material is a multilayer B. All of the layers included in one or more layers are included.

In the present specification, the meaning that the specific A material is included in the C layer or the D layer includes i) one or more of the C layers of one or more layers, ii) one or more of the D layers of the one or more layers, or iii ) It means both included in each of the C layer of one or more layers and D layer of one or more layers.

The organic material layer of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, it 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, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light emitting device is not limited thereto, and may include more or less organic material layers.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is included in the first organic material layer.

In an exemplary embodiment of the present specification, the first organic material layer includes a hole injection layer, a hole transport layer, a hole control layer, an electron blocking layer, a layer or a light emitting layer simultaneously transporting and injecting holes.

In one embodiment of the present specification, the first organic material layer is a light emitting layer.

In one embodiment of the present specification, the light emitting layer includes the compound represented by Chemical Formula 1 as a dopant in the light emitting layer.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is included in an amount of 0.01 parts by weight or more and less than 20 parts by weight based on 100 parts by weight of the total weight of the first organic material layer. More preferably, the first organic material layer is included in an amount of 1 part by weight or more and 10 parts by weight or less compared to 100 parts by weight of the total weight.

In one embodiment of the present specification, the light emitting layer includes a compound represented by Chemical Formula 1, and a light emitting layer including a compound represented by Chemical Formula 1 has a blue color.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes the above-described compound as a dopant in the light emitting layer, and may further include a host.

In one embodiment of the present specification, the first organic material layer is a light emitting layer, and further includes an anthracene derivative in addition to the compound represented by Chemical Formula 1. Specifically, the compound described above is included as a dopant in the light emitting layer, and an anthracene derivative is included as a host in the light emitting layer.

In one embodiment of the present specification, the anthracene derivative is a compound represented by the following formula H01 or H02,

[Formula H01]

[Formula H02]

In the above formula H01 and H02,

D means deuterium, k1 is an integer from 0 to 8, k2 is an integer from 0 to 7,

L21 to L23 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar21 to Ar23 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.

In one embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms containing N, O, or S.

In one embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Or a naphthylene group, L21 to L23 may each contain one or more deuterium.

In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthryl group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group, Ar21 to Ar23 may each contain one or more deuterium.

In one embodiment of the present specification, Ar21 and Ar22 are different from each other.

In one embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar21 is an aryl group unsubstituted or substituted with deuterium, and Ar22 is an aryl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar21 is an aryl group unsubstituted or substituted with deuterium, and Ar22 is a heteroaryl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar23 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar23 is an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar23 is a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or a phenanthryl group.

In one embodiment of the present specification, the anthracene derivative is any one selected from the following compounds.

The compound represented by Chemical Formula H may be included as one type in the organic material layer (specifically, the light emitting layer), or may be included as two or more types. Specifically, the first host represented by Chemical Formula H and the second host represented by Chemical Formula H may be included in the organic material layer.

The weight ratio of the first host represented by Chemical Formula H and the second host represented by Chemical Formula H is 95:5 to 5:95, more preferably 30:70 to 70:30.

In another exemplary embodiment, the first host and the second host are different from each other.

In another exemplary embodiment, Ar21 and Ar22 of the first host represented by Chemical Formula H are the same or different from each other, and each independently an substituted or unsubstituted aryl group; Ar21 of the second host represented by Formula H is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, the organic light emitting device further includes one or more light emitting layers in addition to the light emitting layer including the compound represented by Chemical Formula 1. Each of the one or more light emitting layers may include the above-described fluorescent dopant or phosphorescent dopant.

According to the exemplary embodiment of the present specification, the organic light emitting device includes two or more light emitting layers, one of the two or more light emitting layers includes a fluorescent dopant, and the other layer includes a phosphorescent dopant.

According to an exemplary embodiment of the present invention, a light emitting layer including the compound represented by Chemical Formula 1 is included, and a maximum emission peak of the light emitting layer is 400 nm to 500 nm.

In one embodiment of the present specification, the organic light emitting device includes two or more light emitting layers.

In an exemplary embodiment of the present specification, the maximum emission peak of each light emitting layer is different from each other. Specifically, the organic light emitting device further includes at least one light emitting layer in which a maximum light emission peak appears in a wavelength band different from a wavelength band in which the maximum light emission peak of the light emitting layer including at least one compound represented by Chemical Formula 1 appears.

The maximum emission peak of the emission layer containing the compound represented by Formula 1 is 400 nm to 500 nm, and the maximum emission peak of the emission layer of the other layer is 510 nm to 580 nm; Alternatively, a maximum emission peak of 610 nm or 680 nm may be exhibited.

In one embodiment of the present specification, the light emitting layer other than the light emitting layer containing at least one compound represented by Chemical Formula 1 includes a phosphorescent dopant. Specifically, at least one emission layer in which a maximum emission peak appears in a wavelength band different from a wavelength band in which the maximum emission peak of the emission layer including at least one compound represented by Chemical Formula 1 is included is a phosphorescent dopant.

In one embodiment of the present specification, one layer of the light emitting layer has a blue color, and the other layer of the light emitting layer may include a blue, red, or green light emitting compound known in the art.

According to an exemplary embodiment of the present invention, the organic light emitting device includes two or more light emitting layers, one light emitting layer includes a fluorescent dopant, and the other light emitting layer includes a phosphorescent dopant.

In addition, when the organic light emitting device of the present invention includes two or more light emitting layers, the two or more light emitting layers may be sequentially stacked in the vertical direction, or may be stacked side by side in the horizontal direction.

In one embodiment of the present specification, the organic light emitting device includes three or more light emitting layers. In one embodiment, the three or more light-emitting layers are sequentially stacked, and all of the three or more light-emitting layers may have a maximum emission peak in the same wavelength band. At this time, the maximum emission peak is 400 nm to 500 nm, which is a blue region.

In one embodiment of the present specification, the compound represented by Chemical Formula 2 is included in the second organic material layer.

In an exemplary embodiment of the present specification, the compound represented by Chemical Formula 2 is included in a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or a layer that simultaneously transports and injects electrons.

In one embodiment of the present specification, the second organic material layer includes a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or a layer that simultaneously transports and injects electrons.

In an exemplary embodiment of the present specification, the second organic material layer includes an electron transport layer or a layer that performs electron transport and injection simultaneously.

In one embodiment of the present specification, the first organic material layer and the second organic material layer are provided in contact.

In one embodiment of the present specification, a first organic material layer is provided between the anode and the cathode. In another exemplary embodiment, the second organic material layer is provided between the first organic material layer and the cathode.

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

In one embodiment of the present specification, an electron transport region is further included between the second organic material layer and the first organic material layer.

In one embodiment of the present specification, the second organic material layer is provided in contact with the light emitting layer. Specifically, it is provided in contact with the surface facing the cathode of the light emitting layer.

In one embodiment of the present specification, the second organic material layer further includes one or two or more n-type dopants selected from alkali metals and alkaline earth metals in addition to the compound represented by Chemical Formula 2.

When an organic alkali metal compound or an organic alkaline earth metal compound is used as the n-type dopant, stability against holes can be secured from the light emitting layer, and the life of the organic light emitting device can be improved. In addition, the electron mobility of the electron transport layer can be adjusted to the ratio of the organic alkali metal compound or the organic alkaline earth metal compound to maximize the balance of holes and electrons in the light emitting layer, thereby increasing luminous efficiency.

LiQ is more preferable as an n-type dopant used in the second organic material layer in the present specification. The second organic material layer may include a heterocyclic compound in Formula 2 and the n-type dopant in a weight ratio of 1:9 to 9:1. Preferably, the heterocyclic compound of Formula 1 and the n-type dopant may include 2:8 to 8:2, and more preferably 3:7 to 7:3.

In one embodiment of the present specification, the negative electrode has a multi-layer structure of a metal or a metal alloy.

In one embodiment, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.

In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode. In another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

In one embodiment of the present specification, 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 one embodiment of the present specification, 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.

1 to 4 illustrate the laminated structure of the organic light emitting device of the present invention.

1 shows an organic light emitting device sequentially stacked in a vertical direction in the order of the substrate 0, the cathode 1, the second organic material layer 202, the first organic material layer 201, and the anode 4. In one embodiment of the present specification, the compound represented by Chemical Formula 1 is included in the first organic material layer 201, and the compound represented by Chemical Formula 2 is included in the second organic material layer 202.

2 to 4 each show a stacked structure of the organic light emitting device of the present invention including two or more light emitting layers.

Figure 2 is a substrate (0), cathode (1), electron transport layer (2), hole blocking layer or electron control layer (7), light emitting layer 1 (11), organic material layer (5), light emitting layer 2 (12), hole transport layer ( 3) and the anode 4 are shown organic light emitting devices sequentially stacked in the vertical direction. In one embodiment of the present specification, the compound represented by Chemical Formula 1 is included in the organic material layer 5 or the hole transport layer 3. In one embodiment, the compound represented by Chemical Formula 2 is included in the electron transport layer 2, the hole blocking layer or the electron control layer 7 or the organic material layer 5.

3 is a substrate (0), cathode (1), electron transport layer (2), hole blocking layer or electron control layer (7), light emitting layer 1 (11), organic material layer (5), light emitting layer 2 (12), organic material layer (6) ), a light emitting layer 3 (13), a hole transport layer (3) and an anode (4) in the order shown in the vertical direction sequentially stacked organic light emitting device. In one embodiment of the present specification, the compound represented by Chemical Formula 1 is included in the organic material layer 5, the organic material layer 6, or the hole transport layer 3.

4, the substrate (0), cathode (1), electron transport layer (2), hole blocking layer or electron control layer (7), light emitting layer (101), hole transport layer (3) and anode (4) are stacked in order, The light emitting layer 101 represents an organic light emitting device in which light emitting layers 1 (11) and 2 (12) are stacked side by side in a horizontal direction. In one embodiment of the present specification, the compound represented by Chemical Formula 1 is included in the hole transport layer 3. In one embodiment, the compound represented by Chemical Formula 2 is included in the electron transport layer 2 or the hole blocking layer or the electron control layer 7.

In one embodiment, the compound represented by Chemical Formula 2 is included in the electron transport layer 2, the hole blocking layer or the electron regulating layer 7, the organic material layer 5, or the organic material layer 6. In an exemplary embodiment of the present invention, the emission colors of the emission layer 1 (11), the emission layer 2 (12), and the emission layer 3 (13) are the same. In one embodiment, the light emitting layer 1 (11), the light emitting layer 2 (12) and the light emitting layer 3 (13) are blue.

2 and 3, when a plurality of light emitting layers are stacked, the organic material layer provided between the plurality of light emitting layers may be an intermediate layer. The intermediate layer is also generally called an intermediate electrode, an intermediate conductive layer, a charge generating layer, an electron drawing layer, a connecting layer, and an intermediate insulating layer, and has a function of supplying electrons to the adjacent layer on the anode side and holes to the adjacent layer on the cathode side. If it is a layer, a known material composition can be used. In one embodiment of the present invention, the organic material layer 5 located between the light emitting layer 1 and the light emitting layer 2 is a charge generating layer or an intermediate insulating layer. In one embodiment of the present invention, the organic material layer 6 positioned between the light emitting layer 2 and the light emitting layer 3 is a charge generating layer or an intermediate insulating layer.

However, the structure of the organic light emitting device according to the exemplary embodiment of the present specification is not limited to FIGS. 1 to 4, and may be any of the following structures.

(1) anode/hole transport layer/light emitting layer/cathode

(2) anode/hole injection layer/hole transport layer/light emitting layer/cathode

(3) anode/hole transport layer/light emitting layer/electron transport layer/cathode

(4) anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(5) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode

(6) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(7) anode/hole transport layer/hole control layer/light emitting layer/electron transport layer/cathode

(8) anode/hole transport layer/hole control layer/light emitting layer/electron transport layer/electron injection layer/cathode

(9) anode/hole injection layer/hole transport layer/hole control layer/light emitting layer/electron transport layer/cathode

(10) anode/hole injection layer/hole transport layer/hole control layer/light emitting layer/electron transport layer/electron injection layer/cathode

(11) anode/hole transport layer/light emitting layer/electron control layer/electron transport layer/cathode

(12) Anode/hole transport layer/light emitting layer/electron control layer/electron transport layer/electron injection layer/cathode

(13) anode/hole injection layer/hole transport layer/light emitting layer/electron control layer/electron transport layer/cathode

(14) anode/hole injection layer/hole transport layer/light emitting layer 1/middle layer/light emitting layer 2/electron transport layer/electron injection layer/cathode

(15) anode/hole injection layer/hole transport layer/light emitting layer 1/middle layer/light emitting layer 2/middle layer/light emitting layer 3/electron transport layer/electron injection layer/cathode

In one embodiment of the present invention, the first organic material layer is a light emitting layer, a light emitting layer 1, a light emitting layer 2 or a light emitting layer 3.

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 material layer of the organic light emitting device can be formed in various ways.

In one embodiment, after depositing a metal or conductive metal oxide or an alloy thereof on a substrate to form an anode, 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, An organic light-emitting device can be manufactured by depositing a material that can be used as a cathode thereon.

In another exemplary embodiment, an organic light emitting device may be made by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

Each organic layer can be formed by any conventional deposition technique, such as vapor deposition, liquid deposition (continuous and discontinuous techniques), and thermal transfer. have. Continuous deposition technology includes spin coating, gravure coating, curtain coating, dip coating, slot-die coating, and spray coating. And continuous nozzle coating. Discontinuous deposition techniques include, but are not limited to, ink jet printing, gravure printing, and screen printing.

In one embodiment of the present specification, the first organic material layer and the second organic material layer are deposited using physical vapor deposition (PVD, physical vapor deposition), such as sputtering or e-beam evaporation. Can be formed.

According to another exemplary embodiment, the first organic material layer and the second organic material layer may be formed as an organic material layer by a solution coating method. Here, the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

In one embodiment of the present specification, other layers in the organic light emitting device can be manufactured using any known material, as long as it is useful for each layer. Hereinafter, preferred materials that can be used in the organic material layer are exemplified, but are not limited thereto.

The positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer. Metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : Combination of metal and oxide such as Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There is a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, Pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and periplanene having arylamine groups. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or two or more are selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups. It is substituted or unsubstituted with a substituent. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.

The hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injection effect for the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of the exciton generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. Also, a material having excellent thin film formation ability is preferred. In addition, it is preferable that the high-occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, and arylamine-based organic materials; Hexanitrile hexaaza triphenylene series organics; Quinacridone-based organic matter; Perylene-based organics; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. As the hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is preferably a material having high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having conjugated and non-conjugated portions.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons is preferable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including 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 negative electrode material, as used according to the prior art. Particularly, a suitable negative electrode material has a low work function and is a common material followed by an aluminum layer or a silver layer. Specifically, there 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 receives electrons from an electrode. It is preferable that the electron injecting agent has an excellent electron transporting ability and an electron receiving effect from the second electrode, and an excellent electron injection effect with respect to the light emitting layer or the light emitting material. In addition, a material that prevents exciton generated in the light emitting layer from moving to the hole injection 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 the like and their derivatives, Metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, and 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-naphtolato)gallium, etc. , But is not limited thereto.

The electron blocking layer is a layer capable of improving the life and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer. Known materials can be used without limitation, and can be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and the layer simultaneously performing hole injection and hole transport.

The hole blocking layer is a layer that blocks reaching the cathode of the hole, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but are not limited thereto.

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

Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present application is not interpreted to be limited to the embodiments described below. The embodiments of the present application are provided to more fully describe the present specification to those skilled in the art.

제조예 1-1: 화합물 D1의 제조Preparation Example 1-1: Preparation of Compound D1

Flask containing 1-bromo-2,3-dichlorobenzene (22.6 g), intermediate D1-A (21.4 g), Pd(PtBu3)2 (1.02 g), NaOtBu (38.4 g) and toluene (800 ml) Heated at 110° C. and stirred for 30 minutes. The reaction solution was cooled to room temperature, and sat.aq. After adding NH4Cl and toluene to separate, the solvent was distilled off under reduced pressure. Purification by recrystallization (methyl tert-butyl ether/hexane) gave intermediate D1-B (12.4 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=323.

To a flask containing intermediate D1-B (4.8 g) and tert-butyl benzene (160 ml), 1.7 M tert-butyllithium pentane solution (9.2 ml) was added at 0° C. under an argon atmosphere. After completion of the dropwise addition, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. After cooling to -40°C, boron tribromide (1.6 ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, it was cooled to 0°C again, N,N-diisopropylethylamine (6.6 ml) was added, and the mixture was stirred at room temperature and then stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, separated by adding water and ethyl acetate, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to give D1 (2.3 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=297.

제조예 1-2: 화합물 D2의 제조Preparation Example 1-2: Preparation of Compound D2

A flask containing 3-bromo-4,5-dichlorophenol (24.2 g), intermediate D2-A (33.8 g), Pd(PtBu3)2 (1.02 g), NaOtBu (38.4 g) and toluene (800 ml) Heated at 110° C. and stirred for 30 minutes. The reaction solution was cooled to room temperature, and sat.aq. After adding NH4Cl and toluene to separate, the solvent was distilled off under reduced pressure. Purification by recrystallization (methyl tert-butyl ether/hexane) gave intermediate D2-B (39.4 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=463.

To a flask containing intermediate D2-B (6.9 g) and tert-butyl benzene (160 ml), 1.7 M tert-butyllithium pentane solution (9.2 ml) was added at 0° C. under an argon atmosphere. After completion of the dropwise addition, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. After cooling to -40°C, boron tribromide (1.6 ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, it was cooled to 0°C again, N,N-diisopropylethylamine (6.6 ml) was added, and the mixture was stirred at room temperature and then stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, separated by adding water and ethyl acetate, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain intermediate D2-C (3.2 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+] = 437.

Dissolve intermediate D2-C (2.8 g), nonafluorobutane-1-sulfonyl fluoride (2.2 g) and potassium carbonate (1.5 g) in acetonitrile (40 ml), heat to 50° C. and stir for 4 hours Did. After cooling to room temperature, distilled water was added to remove potassium carbonate to obtain intermediate D2-D (4.3 g).

A flask containing intermediate D2-D (10.7 g), intermediate B-5 (2.5 g), Pd(PtBu3)2 (0.10 g), NaOtBu (3.0 g) and toluene (100 ml) was heated at 110°C, 30 Stir for minutes. The reaction solution was cooled to room temperature, and sat.aq. After adding NH4Cl and toluene to separate, the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography (developer: hexane/ethyl acetate = 50%/50% (volume ratio)) gave D2 (6.2 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+] = 588.

제조예 1-3: 화합물 D3의 제조Preparation Example 1-3: Preparation of Compound D3

A flask containing 3-bromo-4,5-dichlorophenol (24.2 g), intermediate D3-A (56.2 g), Pd(PtBu3)2 (1.02 g), NaOtBu (38.4 g) and toluene (800 ml) Heated at 110° C. and stirred for 30 minutes. The reaction solution was cooled to room temperature, and sat.aq. After adding NH4Cl and toluene to separate, the solvent was distilled off under reduced pressure. Purification by recrystallization (methyl tert-butyl ether/hexane) gave intermediate D3-B (47.2 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+] = 687.

To a flask containing intermediate D3-B (10.2 g) and tert-butyl benzene (160 ml), a 1.7 M tert-butyllithium pentane solution (9.2 ml) was added at 0° C. under an argon atmosphere. After completion of the dropwise addition, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. After cooling to -40°C, boron tribromide (1.6 ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, it was cooled to 0°C again, N,N-diisopropylethylamine (6.6 ml) was added, and the mixture was stirred at room temperature and then stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, separated by adding water and ethyl acetate, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain intermediate D3-C (4.9 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+] = 661.

Dissolve intermediate D3-C (4.2 g), nonafluorobutane-1-sulfonyl fluoride (2.2 g) and potassium carbonate (1.5 g) in acetonitrile (40 ml), heat to 50° C. and stir for 4 hours Did. After cooling to room temperature, distilled water was added to remove potassium carbonate to obtain intermediate D3-D (5.8 g).

A flask containing intermediate D3-D (14.0 g), intermediate C-5 (2.5 g), Pd(PtBu3)2 (0.10 g), NaOtBu (3.0 g) and toluene (100 ml) was heated at 110°C, 30 Stir for minutes. The reaction solution was cooled to room temperature, and sat.aq. After adding NH4Cl and toluene to separate, the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography (developer: hexane/ethyl acetate = 50%/50% (volume ratio)) gave D3 (7.7 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=810.

제조예 1-4: 화합물 D4의 제조Preparation Example 1-4: Preparation of Compound D4

1-bromo-2,3-dichloro-5-methylbenzene (24.0 g), intermediate D4-A (28.8 g), Pd(PtBu3)2 (0.51 g), NaOtBu (19.2 g) and toluene (400 ml) This flask was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, and sat.aq. After adding NH4Cl and toluene to separate, the solvent was distilled off under reduced pressure. Purification by recrystallization (methyl tert-butyl ether/hexane) gave intermediate D4-B (33.0 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=440.

The flask containing intermediate D4-B (19.3 g), intermediate D4-C (18.1 g), Pd(PtBu3)2 (0.22 g), NaOtBu (8.42 g) and toluene (400 ml) was heated at 110°C, 30 Stir for minutes. The reaction solution was cooled to room temperature, and sat.aq. After adding NH4Cl and toluene to separate, the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography (developer: hexane/ethyl acetate = 50%/50% (volume ratio)) gave intermediate D4-D (18.0 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=817.

To a flask containing intermediate D4-D (12.2 g) and tert-butyl benzene (160 ml), a 1.7 M tert-butyllithium pentane solution (9.2 ml) was added at 0° C. under an argon atmosphere. After completion of the dropwise addition, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. After cooling to -40°C, boron tribromide (1.6 ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, it was cooled to 0°C again, N,N-diisopropylethylamine (6.6 ml) was added, and the mixture was stirred at room temperature and then stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, separated by adding water and ethyl acetate, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to give D4 (6.4 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=791.

제조예 1-5: 화합물 D5의 제조Preparation Example 1-5: Preparation of Compound D5

1-bromo-2,3-dichloro-5-methylbenzene (24.0 g), intermediate D5-A (56.4 g), Pd(PtBu3)2 (1.02 g), NaOtBu (38.4 g) and toluene (800 ml) This flask was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, and sat.aq. After adding NH4Cl and toluene to separate, the solvent was distilled off under reduced pressure. Purification by recrystallization (methyl tert-butyl ether/hexane) gave intermediate D5-B (99.8 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=685.

To a flask containing intermediate D5-B (10.2 g) and tert-butyl benzene (160 ml), a 1.7 M tert-butyllithium pentane solution (9.2 ml) was added at 0°C under an argon atmosphere. After completion of the dropwise addition, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. After cooling to -40°C, boron tribromide (1.6 ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, it was cooled to 0°C again, N,N-diisopropylethylamine (6.6 ml) was added, and the mixture was stirred at room temperature and then stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, separated by adding water and ethyl acetate, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to give D5 (5.2 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=659.

제조예 1-6: 화합물 D6의 제조Preparation Example 1-6: Preparation of Compound D6

1-bromo-2,3-dichloro-5-methylbenzene (24.0 g), intermediate D6-A (17.3 g), Pd(PtBu3)2 (0.51 g), NaOtBu (19.2 g) and toluene (400 ml) The flask was heated at 110° C. and stirred for 30 minutes. The reaction solution was cooled to room temperature, and sat.aq. After adding NH4Cl and toluene to separate, the solvent was distilled off under reduced pressure. Purification by recrystallization (methyl tert-butyl ether/hexane) gave intermediate D6-B (24.6 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=328.

The flask containing intermediate D6-B (14.4 g), intermediate D6-C (14.7 g), Pd(PtBu3)2 (0.22 g), NaOtBu (8.42 g) and toluene (400 ml) was heated at 110°C, 30 Stir for minutes. The reaction solution was cooled to room temperature, and sat.aq. After adding NH4Cl and toluene to separate, the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography (developer: hexane/ethyl acetate = 50%/50% (volume ratio)) gave intermediate D6-D (14.0 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+] = 627.

To a flask containing intermediate D6-D (9.4 g) and tert-butyl benzene (160 ml), a 1.7 M tert-butyllithium pentane solution (9.2 ml) was added at 0° C. under an argon atmosphere. After completion of the dropwise addition, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. After cooling to -40°C, boron tribromide (1.6 ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, it was cooled to 0°C again, N,N-diisopropylethylamine (6.6 ml) was added, and the mixture was stirred at room temperature and then stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, separated by adding water and ethyl acetate, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to give D6 (4.4 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=601.

제조예 1-7: 화합물 D7의 제조Preparation Example 1-7: Preparation of compound D7

1-bromo-2,3-dichloro-5-methylbenzene (22.6 g), intermediate D7-A (28.8 g), Pd(PtBu3)2 (0.51 g), NaOtBu (19.2 g) and toluene (400 ml) This flask was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, and sat.aq. After adding NH4Cl and toluene to separate, the solvent was distilled off under reduced pressure. Purification by recrystallization (methyl tert-butyl ether/hexane) gave intermediate D7-B (30.1 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=426.

The flask with intermediate D7-B (18.7 g), intermediate D7-C (15.4 g), Pd(PtBu3)2 (0.22 g), NaOtBu (8.42 g) and toluene (400 ml) was heated at 110°C, 30 Stir for minutes. The reaction solution was cooled to room temperature, and sat.aq. After adding NH4Cl and toluene to separate, the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography (developer: hexane/ethyl acetate = 50%/50% (volume ratio)) gave intermediate D7-D (15.5 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=741.

To a flask containing intermediate D7-D (11.1 g) and tert-butyl benzene (160 ml), 1.7 M tert-butyllithium pentane solution (9.2 ml) was added at 0° C. under an argon atmosphere. After completion of the dropwise addition, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. After cooling to -40°C, boron tribromide (1.6 ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, it was cooled to 0°C again, N,N-diisopropylethylamine (6.6 ml) was added, and the mixture was stirred at room temperature and then stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, separated by adding water and ethyl acetate, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to give D7 (5.2 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=715.

제조예 1-8: 화합물 D8의 제조Preparation Example 1-8: Preparation of Compound D8

Flask containing 1-bromo-2,3-dichlorobenzene (22.6 g), intermediate D8-A (16.9 g), Pd(PtBu3)2 (0.51 g), NaOtBu (19.2 g) and toluene (400 ml) Heated at 110° C. and stirred for 30 minutes. The reaction solution was cooled to room temperature, and sat.aq. After adding NH4Cl and toluene to separate, the solvent was distilled off under reduced pressure. Purification by recrystallization (methyl tert-butyl ether/hexane) gave intermediate D8-B (25.5 g). As a result of measuring the mass spectrum of the obtained solid, a peak was confirmed at [M+H+]=315.

The flask with intermediate D8-B (20.0 g), intermediate D8-C (13.9 g), Pd(PtBu3)2 (0.33 g), NaOtBu (12.23 g) and toluene (400 ml) was heated at 110°C, 30 Stir for minutes. The reaction solution was cooled to room temperature, and sat.aq. After adding NH4Cl and toluene to separate, the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography (developer: hexane/ethyl acetate = 50%/50% (volume ratio)) gave intermediate D8-D (9.8 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+] = 497.

To a flask containing intermediate D8-D (7.4 g) and tert-butyl benzene (160 ml), 1.7 M tert-butyllithium pentane solution (9.2 ml) was added at 0° C. under an argon atmosphere. After completion of the dropwise addition, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. After cooling to -40°C, boron tribromide (1.6 ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, it was cooled to 0°C again, N,N-diisopropylethylamine (6.6 ml) was added, and the mixture was stirred at room temperature and then stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, separated by adding water and ethyl acetate, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to give D8 (2.2 g). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=471.

제조예 2-1: 화합물 E1의 제조Preparation Example 2-1: Preparation of Compound E1

In a nitrogen atmosphere, E1-A (20 g, 43.6 mmol) and E1-B (10.5 g, 43.6 mmol) were added to 400 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (18.1 g, 130.9 mmol) was dissolved in 18 ml of water, stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (1.5 g, 1.3 mmol) was added. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in 468 mL of 20 times chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was white solid compound E1 (13.1 g, 56%, MS: [M+H] + = 537) by recrystallization of chloroform and ethyl acetate.

제조예 2-2: 화합물 E2의 제조Preparation Example 2-2: Preparation of Compound E2

The E2 compound was prepared in the same manner as in Production Example 2-1, except that each starting material was in the same manner as in the above reaction formula.

MS: [M+H] ⁺ = 614

제조예 2-3: 화합물 E3의 제조Preparation Example 2-3: Preparation of compound E3

The E3 compound was prepared in the same manner as in Production Example 2-1, except that each starting material was in the same manner as in the above scheme.

MS: [M+H] ⁺ = 639

제조예 2-4: 화합물 E4의 제조Preparation Example 2-4: Preparation of compound E4

The E4 compound was prepared in the same manner as in Production Example 2-1, except that each starting material was as in the above reaction scheme.

MS: [M+H] ⁺ = 716

제조예 2-5: 화합물 E5의 제조Preparation Example 2-5: Preparation of compound E5

The E5 compound was prepared in the same manner as in Production Example 2-1, except that each starting material was in the same manner as in the above scheme.

MS: [M+H] ⁺ = 640

제조예 2-6: 화합물 E6의 제조Preparation Example 2-6: Preparation of Compound E6

The E6 compound was prepared in the same manner as in Production Example 2-1, except that each starting material was as in the above reaction scheme.

MS: [M+H] ⁺ =746

제조예 2-7: 화합물 E7의 제조Preparation Example 2-7: Preparation of compound E7

The E7 compound was prepared in the same manner as in Production Example 2-1, except that each starting material was in the same manner as in the above scheme.

MS: [M+H] ⁺ = 729

제조예 2-8: 화합물 E8의 제조Preparation Example 2-8: Preparation of compound E8

The E8 compound was prepared in the same manner as in Production Example 2-1, except that each starting material was in the same manner as in the above scheme.

MS: [M+H] ⁺ = 795

제조예 2-9: 화합물 E9의 제조Preparation Example 2-9: Preparation of compound E9

The E9 compound was prepared in the same manner as in Production Example 2-1, except that each starting material was as in the above reaction scheme.

MS: [M+H] ⁺ = 763

제조예 2-10: 화합물 E10의 제조Preparation Example 2-10: Preparation of compound E10

The E10 compound was prepared by the same method as the production method of Preparation Example 2-1, except that each starting material was as in the above reaction scheme.

MS: [M+H] ⁺ = 808

제조예 2-11: 화합물 E11의 제조Preparation Example 2-11: Preparation of Compound E11

The E11 compound was prepared by the same method as the production method of Preparation Example 2-1, except that each starting material was the same as the reaction scheme.

MS: [M+H] ⁺ = 741

제조예 2-12: 화합물 E12의 제조Preparation Example 2-12: Preparation of Compound E12

The E12 compound was prepared in the same manner as in Production Example 2-1, except that each starting material was as in the above reaction scheme.

MS: [M+H] ⁺ = 679

제조예 2-13: 화합물 E13의 제조Preparation Example 2-13: Preparation of compound E13

In a nitrogen atmosphere, E13-A (20 g, 34.2 mmol) and E13-B (18.4 g, 68.4 mmol) were added to 400 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (14.2 g, 102.7 mmol) was dissolved in 14 ml of water, stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (1.2 g, 1 mmol) was added. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in 544 mL of chloroform 20 times, dissolved twice, washed with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered to distill the filtrate under reduced pressure. A white solid compound E13 (18 g, 66%, MS: [M+H] + =795) was prepared by recrystallizing the concentrated compound from chloroform and ethyl acetate.

실험예 1-1Experimental Example 1-1

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

The following compound HI-A was thermally vacuum-deposited to a thickness of 100 증착 on the prepared ITO transparent electrode to form a hole injection layer. On the hole injection layer, the following compound HAT was sequentially vacuum-deposited to a thickness of 50 Å to a first hole transport layer and the following compound HT-A to a thickness of 700 진공 to form a second hole transport layer. The following compound HT-B was vacuum-deposited to a thickness of 100 MPa on the hole transport layer to form an electron blocking layer. On the electron blocking layer, the following compound BH and compound D1 prepared above were vacuum-deposited to a thickness of 200 Pa in a weight ratio of 25:1 to form a blue light emitting layer. On the blue light-emitting layer, the compound E1 prepared above was vacuum-deposited to a thickness of 100 Å to form an electron transport layer. On the electron transport layer, the following compounds ET-A and lithium (Li) were vacuum deposited to a thickness of 100 로 at a weight ratio of 100:1 to form an electron injection layer. Aluminum was deposited on the electron injection layer to a thickness of 1000 Å to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å/sec, and the aluminum at the cathode maintained a deposition rate of 2 Å/sec, and the vacuum degree during deposition was 1×10 ^-7 to 5×10 ^-5 torr. To maintain an organic light emitting device.

실시예 1-2 내지 1-104 Examples 1-2 to 1-104

In Example 1-1, an organic light emitting device was manufactured according to the same method as Example 1-1 except for using the compound of Table 1 below instead of the compound D1 and/or E1.

비교예 1-1 내지 1-21Comparative Examples 1-1 to 1-21

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

	청색도펀트Blue dopant	전자수송층Electron transport layer	전압(V)Voltage (V)	효율(cd/A)Efficiency (cd/A)	색좌표(x, y)Color coordinate (x, y)	T90(hr)T90(hr)
실시예 1-1Example 1-1	D1D1	E1E1	4.054.05	4.064.06	(0.139, 0.062)(0.139, 0.062)	221221
실시예 1-2Example 1-2	D1D1	E2E2	3.973.97	4.264.26	(0.139, 0.062)(0.139, 0.062)	190190
실시예 1-3Example 1-3	D1D1	E3E3	3.933.93	4.104.10	(0.139, 0.062)(0.139, 0.062)	214214
실시예 1-4Example 1-4	D1D1	E4E4	3.953.95	4.304.30	(0.140, 0.062)(0.140, 0.062)	183183
실시예 1-5Example 1-5	D1D1	E5E5	4.094.09	4.144.14	(0.139, 0.061)(0.139, 0.061)	175175
실시예 1-6Example 1-6	D1D1	E6E6	4.014.01	4.124.12	(0.139, 0.062)(0.139, 0.062)	216216
실시예 1-7Example 1-7	D1D1	E7E7	3.973.97	4.254.25	(0.139, 0.062)(0.139, 0.062)	193193
실시예 1-8Example 1-8	D1D1	E8E8	4.014.01	4.154.15	(0.140, 0.062)(0.140, 0.062)	182182
실시예 1-9Example 1-9	D1D1	E9E9	3.953.95	4.354.35	(0.139, 0.061)(0.139, 0.061)	170170
실시예 1-10Example 1-10	D1D1	E10E10	3.993.99	4.254.25	(0.139, 0.062)(0.139, 0.062)	177177
실시예 1-11Example 1-11	D1D1	E11E11	4.104.10	4.004.00	(0.139, 0.062)(0.139, 0.062)	267267
실시예 1-12Example 1-12	D1D1	E12E12	4.044.04	4.084.08	(0.140, 0.062)(0.140, 0.062)	211211
실시예 1-13Example 1-13	D1D1	E13E13	4.134.13	4.014.01	(0.139, 0.061)(0.139, 0.061)	180180
실시예 1-14Example 1-14	D2D2	E1E1	4.034.03	4.044.04	(0.139, 0.062)(0.139, 0.062)	215215
실시예 1-15Example 1-15	D2D2	E2E2	3.953.95	4.244.24	(0.139, 0.062)(0.139, 0.062)	185185
실시예 1-16Example 1-16	D2D2	E3E3	3.903.90	4.084.08	(0.140, 0.062)(0.140, 0.062)	209209
실시예 1-17Examples 1-17	D2D2	E4E4	3.933.93	4.284.28	(0.139, 0.061)(0.139, 0.061)	179179
실시예 1-18Example 1-18	D2D2	E5E5	4.074.07	4.124.12	(0.139, 0.062)(0.139, 0.062)	170170
실시예 1-19Examples 1-19	D2D2	E6E6	3.993.99	4.094.09	(0.139, 0.062)(0.139, 0.062)	210210
실시예 1-20Example 1-20	D2D2	E7E7	3.953.95	4.234.23	(0.139, 0.062)(0.139, 0.062)	188188
실시예 1-21Example 1-21	D2D2	E8E8	3.993.99	4.124.12	(0.140, 0.062)(0.140, 0.062)	177177
실시예 1-22Example 1-22	D2D2	E9E9	3.933.93	4.334.33	(0.139, 0.061)(0.139, 0.061)	166166
실시예 1-23Example 1-23	D2D2	E10E10	3.963.96	4.234.23	(0.140, 0.062)(0.140, 0.062)	173173
실시예 1-24Example 1-24	D2D2	E11E11	4.074.07	3.983.98	(0.139, 0.061)(0.139, 0.061)	261261
실시예 1-25Example 1-25	D2D2	E12E12	4.024.02	4.064.06	(0.139, 0.062)(0.139, 0.062)	206206
실시예 1-26Example 1-26	D2D2	E13E13	4.114.11	3.983.98	(0.139, 0.062)(0.139, 0.062)	175175
실시예 1-27Example 1-27	D3D3	E1E1	4.014.01	4.034.03	(0.140, 0.062)(0.140, 0.062)	211211
실시예 1-28Example 1-28	D3D3	E2E2	3.933.93	4.234.23	(0.140, 0.062)(0.140, 0.062)	182182
실시예 1-29Example 1-29	D3D3	E3E3	3.893.89	4.074.07	(0.139, 0.061)(0.139, 0.061)	205205
실시예 1-30Example 1-30	D3D3	E4E4	3.913.91	4.274.27	(0.139, 0.062)(0.139, 0.062)	175175
실시예 1-31Examples 1-31	D3D3	E5E5	4.054.05	4.114.11	(0.140, 0.062)(0.140, 0.062)	167167
실시예 1-32Examples 1-32	D3D3	E6E6	3.973.97	4.094.09	(0.139, 0.061)(0.139, 0.061)	206206
실시예 1-33Examples 1-33	D3D3	E7E7	3.933.93	4.224.22	(0.139, 0.062)(0.139, 0.062)	184184
실시예 1-34Examples 1-34	D3D3	E8E8	3.973.97	4.124.12	(0.139, 0.062)(0.139, 0.062)	173173
실시예 1-35Examples 1-35	D3D3	E9E9	3.923.92	4.324.32	(0.140, 0.062)(0.140, 0.062)	163163
실시예 1-36Examples 1-36	D3D3	E10E10	3.953.95	4.224.22	(0.139, 0.061)(0.139, 0.061)	169169
실시예 1-37Examples 1-37	D3D3	E11E11	4.064.06	3.973.97	(0.139, 0.062)(0.139, 0.062)	255255
실시예 1-38Examples 1-38	D3D3	E12E12	4.014.01	4.054.05	(0.140, 0.062)(0.140, 0.062)	202202
실시예 1-39Example 1-39	D3D3	E13E13	4.094.09	3.983.98	(0.139, 0.061)(0.139, 0.061)	172172
실시예 1-40Example 1-40	D4D4	E1E1	4.014.01	4.124.12	(0.139, 0.062)(0.139, 0.062)	187187
실시예 1-41Examples 1-41	D4D4	E2E2	3.933.93	4.324.32	(0.139, 0.062)(0.139, 0.062)	160160
실시예 1-42Examples 1-42	D4D4	E3E3	3.893.89	4.164.16	(0.139, 0.062)(0.139, 0.062)	181181
실시예 1-43Examples 1-43	D4D4	E4E4	3.913.91	4.364.36	(0.139, 0.062)(0.139, 0.062)	155155
실시예 1-44Examples 1-44	D4D4	E5E5	4.054.05	4.204.20	(0.140, 0.062)(0.140, 0.062)	147147
실시예 1-45Examples 1-45	D4D4	E6E6	3.973.97	4.174.17	(0.139, 0.061)(0.139, 0.061)	182182
실시예 1-46Examples 1-46	D4D4	E7E7	3.933.93	4.314.31	(0.139, 0.062)(0.139, 0.062)	163163
실시예 1-47Examples 1-47	D4D4	E8E8	3.973.97	4.204.20	(0.139, 0.062)(0.139, 0.062)	153153
실시예 1-48Examples 1-48	D4D4	E9E9	3.913.91	4.414.41	(0.140, 0.062)(0.140, 0.062)	144144
실시예 1-49Examples 1-49	D4D4	E10E10	3.953.95	4.314.31	(0.139, 0.061)(0.139, 0.061)	149149
실시예 1-50Example 1-50	D4D4	E11E11	4.064.06	4.064.06	(0.139, 0.062)(0.139, 0.062)	226226
실시예 1-51Examples 1-51	D4D4	E12E12	4.004.00	4.144.14	(0.139, 0.062)(0.139, 0.062)	179179
실시예 1-52Examples 1-52	D4D4	E13E13	4.094.09	4.064.06	(0.139, 0.062)(0.139, 0.062)	152152
실시예 1-53Examples 1-53	D5D5	E1E1	4.024.02	4.144.14	(0.140, 0.062)(0.140, 0.062)	179179
실시예 1-54Examples 1-54	D5D5	E2E2	3.943.94	4.354.35	(0.139, 0.061)(0.139, 0.061)	154154
실시예 1-55Examples 1-55	D5D5	E3E3	3.903.90	4.184.18	(0.139, 0.062)(0.139, 0.062)	174174
실시예 1-56Examples 1-56	D5D5	E4E4	3.923.92	4.394.39	(0.139, 0.062)(0.139, 0.062)	149149
실시예 1-57Examples 1-57	D5D5	E5E5	4.064.06	4.224.22	(0.139, 0.062)(0.139, 0.062)	141141
실시예 1-58Examples 1-58	D5D5	E6E6	3.983.98	4.204.20	(0.140, 0.062)(0.140, 0.062)	175175
실시예 1-59Examples 1-59	D5D5	E7E7	3.943.94	4.344.34	(0.139, 0.061)(0.139, 0.061)	156156
실시예 1-60Examples 1-60	D5D5	E8E8	3.983.98	4.234.23	(0.140, 0.062)(0.140, 0.062)	147147
실시예 1-61Examples 1-61	D5D5	E9E9	3.923.92	4.444.44	(0.139, 0.061)(0.139, 0.061)	138138
실시예 1-62Examples 1-62	D5D5	E10E10	3.953.95	4.344.34	(0.139, 0.062)(0.139, 0.062)	143143
실시예 1-63Examples 1-63	D5D5	E11E11	4.064.06	4.084.08	(0.139, 0.062)(0.139, 0.062)	217217
실시예 1-64Examples 1-64	D5D5	E12E12	4.014.01	4.164.16	(0.140, 0.062)(0.140, 0.062)	171171
실시예 1-65Examples 1-65	D5D5	E13E13	4.104.10	4.094.09	(0.140, 0.062)(0.140, 0.062)	146146
실시예 1-66Examples 1-66	D6D6	E1E1	3.993.99	4.204.20	(0.139, 0.061)(0.139, 0.061)	203203
실시예 1-67Examples 1-67	D6D6	E2E2	3.913.91	4.414.41	(0.139, 0.062)(0.139, 0.062)	175175
실시예 1-68Examples 1-68	D6D6	E3E3	3.873.87	4.244.24	(0.140, 0.062)(0.140, 0.062)	197197
실시예 1-69Examples 1-69	D6D6	E4E4	3.893.89	4.454.45	(0.139, 0.061)(0.139, 0.061)	169169
실시예 1-70Examples 1-70	D6D6	E5E5	4.034.03	4.284.28	(0.139, 0.062)(0.139, 0.062)	161161
실시예 1-71Examples 1-71	D6D6	E6E6	3.953.95	4.264.26	(0.139, 0.062)(0.139, 0.062)	198198
실시예 1-72Examples 1-72	D6D6	E7E7	3.913.91	4.404.40	(0.140, 0.062)(0.140, 0.062)	177177
실시예 1-73Examples 1-73	D6D6	E8E8	3.953.95	4.294.29	(0.139, 0.061)(0.139, 0.061)	167167
실시예 1-74Examples 1-74	D6D6	E9E9	3.893.89	4.504.50	(0.139, 0.062)(0.139, 0.062)	157157
실시예 1-75Examples 1-75	D6D6	E10E10	3.933.93	4.404.40	(0.140, 0.062)(0.140, 0.062)	163163
실시예 1-76Examples 1-76	D6D6	E11E11	4.034.03	4.144.14	(0.139, 0.061)(0.139, 0.061)	246246
실시예 1-77Examples 1-77	D6D6	E12E12	3.983.98	4.224.22	(0.139, 0.062)(0.139, 0.062)	195195
실시예 1-78Examples 1-78	D6D6	E13E13	4.074.07	4.144.14	(0.139, 0.062)(0.139, 0.062)	166166
실시예 1-79Examples 1-79	D7D7	E1E1	3.973.97	4.224.22	(0.139, 0.062)(0.139, 0.062)	194194
실시예 1-80Examples 1-80	D7D7	E2E2	3.893.89	4.434.43	(0.139, 0.062)(0.139, 0.062)	167167
실시예 1-81Examples 1-81	D7D7	E3E3	3.853.85	4.264.26	(0.140, 0.062)(0.140, 0.062)	189189
실시예 1-82Examples 1-82	D7D7	E4E4	3.873.87	4.484.48	(0.139, 0.061)(0.139, 0.061)	161161
실시예 1-83Examples 1-83	D7D7	E5E5	4.014.01	4.314.31	(0.139, 0.062)(0.139, 0.062)	154154
실시예 1-84Examples 1-84	D7D7	E6E6	3.933.93	4.284.28	(0.139, 0.062)(0.139, 0.062)	190190
실시예 1-85Examples 1-85	D7D7	E7E7	3.893.89	4.424.42	(0.140, 0.062)(0.140, 0.062)	170170
실시예 1-86Example 1-86	D7D7	E8E8	3.933.93	4.314.31	(0.139, 0.061)(0.139, 0.061)	160160
실시예 1-87Examples 1-87	D7D7	E9E9	3.873.87	4.534.53	(0.139, 0.062)(0.139, 0.062)	150150
실시예 1-88Examples 1-88	D7D7	E10E10	3.913.91	4.424.42	(0.139, 0.062)(0.139, 0.062)	156156
실시예 1-89Examples 1-89	D7D7	E11E11	4.014.01	4.164.16	(0.139, 0.062)(0.139, 0.062)	235235
실시예 1-90Examples 1-90	D7D7	E12E12	3.963.96	4.254.25	(0.139, 0.061)(0.139, 0.061)	186186
실시예 1-91Examples 1-91	D7D7	E13E13	4.054.05	4.174.17	(0.139, 0.062)(0.139, 0.062)	158158
실시예 1-92Examples 1-92	D8D8	E1E1	4.094.09	3.993.99	(0.140, 0.062)(0.140, 0.062)	232232
실시예 1-93Example 1-93	D8D8	E2E2	4.014.01	4.194.19	(0.139, 0.061)(0.139, 0.061)	200200
실시예 1-94Examples 1-94	D8D8	E3E3	3.973.97	4.034.03	(0.139, 0.062)(0.139, 0.062)	225225
실시예 1-95Examples 1-95	D8D8	E4E4	3.993.99	4.234.23	(0.139, 0.062)(0.139, 0.062)	193193
실시예 1-96Examples 1-96	D8D8	E5E5	4.144.14	4.074.07	(0.140, 0.062)(0.140, 0.062)	183183
실시예 1-97Example 1-97	D8D8	E6E6	4.054.05	4.044.04	(0.139, 0.061)(0.139, 0.061)	226226
실시예 1-98Examples 1-98	D8D8	E7E7	4.014.01	4.174.17	(0.139, 0.062)(0.139, 0.062)	202202
실시예 1-99Examples 1-99	D8D8	E8E8	4.054.05	4.074.07	(0.140, 0.062)(0.140, 0.062)	191191
실시예 1-100Example 1-100	D8D8	E9E9	4.004.00	4.274.27	(0.139, 0.061)(0.139, 0.061)	179179
실시예 1-101Examples 1-101	D8D8	E10E10	4.034.03	4.184.18	(0.139, 0.062)(0.139, 0.062)	186186
실시예 1-102Examples 1-102	D8D8	E11E11	4.144.14	3.933.93	(0.139, 0.062)(0.139, 0.062)	281281
실시예 1-103Example 1-103	D8D8	E12E12	4.094.09	4.014.01	(0.139, 0.062)(0.139, 0.062)	222222
실시예 1-104Examples 1-104	D8D8	E13E13	4.184.18	3.943.94	(0.139, 0.062)(0.139, 0.062)	189189
비교예 1-1Comparative Example 1-1	D1D1	ET-BET-B	4.134.13	3.863.86	(0.140, 0.062)(0.140, 0.062)	7373
비교예 1-2Comparative Example 1-2	D2D2	ET-BET-B	4.114.11	3.833.83	(0.139, 0.061)(0.139, 0.061)	7575
비교예 1-3Comparative Example 1-3	D3D3	ET-BET-B	4.094.09	3.833.83	(0.139, 0.062)(0.139, 0.062)	7272
비교예 1-4Comparative Example 1-4	D4D4	ET-BET-B	4.094.09	3.913.91	(0.139, 0.062)(0.139, 0.062)	7171
비교예 1-5Comparative Example 1-5	D5D5	ET-BET-B	4.104.10	3.933.93	(0.140, 0.062)(0.140, 0.062)	6464
비교예 1-6Comparative Example 1-6	D6D6	ET-BET-B	4.074.07	3.993.99	(0.139, 0.061)(0.139, 0.061)	7171
비교예 1-7Comparative Example 1-7	D7D7	ET-BET-B	4.054.05	4.014.01	(0.139, 0.062)(0.139, 0.062)	6868
비교예 1-8Comparative Example 1-8	D8D8	ET-BET-B	4.184.18	3.793.79	(0.139, 0.062)(0.139, 0.062)	8484
비교예 1-9Comparative Example 1-9	BD-ABD-A	E1E1	4.374.37	2.762.76	(0.139, 0.062)(0.139, 0.062)	170170
비교예 1-10Comparative Example 1-10	BD-ABD-A	E2E2	4.294.29	2.902.90	(0.139, 0.062)(0.139, 0.062)	146146
비교예 1-11Comparative Example 1-11	BD-ABD-A	E3E3	4.244.24	2.792.79	(0.139, 0.062)(0.139, 0.062)	165165
비교예 1-12Comparative Example 1-12	BD-ABD-A	E4E4	4.264.26	2.932.93	(0.139, 0.062)(0.139, 0.062)	141141
비교예 1-13Comparative Example 1-13	BD-ABD-A	E5E5	4.424.42	2.822.82	(0.140, 0.062)(0.140, 0.062)	134134
비교예 1-14Comparative Example 1-14	BD-ABD-A	E6E6	4.334.33	2.802.80	(0.139, 0.061)(0.139, 0.061)	166166
비교예 1-15Comparative Example 1-15	BD-ABD-A	E7E7	4.294.29	2.892.89	(0.139, 0.062)(0.139, 0.062)	148148
비교예 1-16Comparative Example 1-16	BD-ABD-A	E8E8	4.334.33	2.822.82	(0.139, 0.062)(0.139, 0.062)	140140
비교예 1-17Comparative Example 1-17	BD-ABD-A	E9E9	4.274.27	2.962.96	(0.140, 0.062)(0.140, 0.062)	131131
비교예 1-18Comparative Example 1-18	BD-ABD-A	E10E10	4.304.30	2.892.89	(0.139, 0.061)(0.139, 0.061)	136136
비교예 1-19Comparative Example 1-19	BD-ABD-A	E11E11	4.424.42	2.722.72	(0.139, 0.062)(0.139, 0.062)	206206
비교예 1-20Comparative Example 1-20	BD-ABD-A	E12E12	4.374.37	2.782.78	(0.140, 0.062)(0.140, 0.062)	163163
비교예 1-21Comparative Example 1-21	BD-ABD-A	E13E13	4.464.46	2.722.72	(0.139, 0.061)(0.139, 0.061)	139139

It can be seen from Table 1 that the organic light-emitting device including both the compounds of Formulas 1 and 2 has characteristics of high efficiency, low voltage, and long life. Specifically, when comparing Examples 1-1 to 1-104 and Comparative Examples 1-1 to 1-8 of the present invention, it can be seen that the device has low voltage and long life characteristics by including the compound of Formula 2 of the present invention. , When comparing Examples 1-1 to 1-104 and Comparative Examples 1-9 and 1-21 of the present invention, it can be seen that the device has high efficiency characteristics by including the compound of Formula 1 of the present invention. Therefore, when the compound of Formula 1 having high efficiency characteristics and the compound of Formula 2 having low voltage and long life characteristics are used together, the insufficient characteristics of the compound of Formula 1 and the compound of Formula 2 can be complemented with each other to realize a more excellent device.

Claims

anode; cathode; An organic light emitting device comprising a first organic material layer and a second organic material layer provided between the anode and the cathode,

The first organic material layer includes a compound represented by Formula 1 below,

The second organic material layer is an organic light emitting device comprising a compound represented by the following formula (2):

[Formula 1]

In Chemical Formula 1,

X is B; P=O; Or P=S,

Z1 to Z3 are the same as or different from each other, and each independently a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring,

A1 is N(R101) or O, A2 is N(R102) or O,

R101 and R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

[Formula 2]

In Chemical Formula 2,

Y is O; Or S,

R21 to R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, represented by the following formula (3), or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

At least one of R21 to R24 is represented by the following formula (3),

r21 to r24 are the same or different from each other, each independently an integer of 0 to 4, and when r21 is 2 or more, R21 is the same or different from each other, and when r22 is 2 or more, R22 is the same or different from each other, and r23 is 2 or more. R23 is the same or different from each other, and when r24 is 2 or more, R24 is the same or different from each other,

[Formula 3]

In Chemical Formula 3,

X1 is N or C(R31), X2 is N or C(R32), X3 is N or C(R33), and one or more of X1 to X3 is N,

R31, R32 and R33 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted aromatic hydrocarbon ring in combination with Ar1 or Ar2; Or form a substituted or unsubstituted heteroring,

Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with R41; Or a heterocyclic group unsubstituted or substituted with R42, or an aromatic hydrocarbon ring substituted or unsubstituted with R31, R32 or R33; Or form a substituted or unsubstituted heteroring,

R41 and R42 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; Alkyl groups; Haloalkyl group; Alkoxy groups; Silyl group; Aryl group; And a heterocyclic group, or two or more substituents are connected,

L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

m is an integer from 0 to 4, and when 2 or more, L is the same or different from each other

* Is a site that binds to Formula 2.
The method according to claim 1, wherein the formula 3 is an organic light emitting device represented by any one of the following formulas 301 to 303:

[Chemical Formula 301]

[Chemical Formula 302]

[Formula 303]

In the above formulas 301 to 303,

L, m, Ar1 and Ar2 are defined as in Chemical Formula 3,

At least one of X1 to X3 is N, the other is CH or CD,

R30 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r30 is an integer from 0 to 4, and when r30 is 2 or more, R30 is the same or different from each other.
The method according to claim 1, wherein the formula 2 is an organic light emitting device represented by any one of the following formulas 201 to 204:

[Formula 201]

[Formula 202]

[Formula 203]

[Formula 204]

In Chemical Formulas 201 to 204,

X1 to X3, L, m, Ar1, Ar2, R21 to R24, r21 to r24 and Y are the same as defined in Formula 2,

X4 is N or C(R34), X5 is N or C(R35), X6 is N or C(R36), and one or more of X4 to X6 is N,

R34, R35 and R36 are the same as or different from each other, and each independently hydrogen; Or deuterium, or a substituted or unsubstituted aromatic hydrocarbon ring in combination with Ar3 or Ar4; Or form a substituted or unsubstituted heteroring,

Ar3 and Ar4 are the same as or different from each other, and each independently an aryl group substituted or unsubstituted with R43; Or a heterocyclic group unsubstituted or substituted with R44, or an aromatic hydrocarbon ring substituted or unsubstituted with R34, R35 or R36; Or form a substituted or unsubstituted heteroring,

R43 and R44 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; Alkyl groups; Haloalkyl group; Alkoxy groups; Silyl group; Aryl group; And a heterocyclic group, or two or more substituents are connected,

L11 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

m11 is an integer of 0-4, and when it is 2 or more, L11 is the same or different from each other.
The method according to claim 1, wherein the formula 2 is an organic light emitting device represented by any one of the following formula 211 to 218:

[Formula 211]

[Formula 212]

[Formula 213]

[Formula 214]

[Formula 215]

[Formula 216]

[Formula 217]

[Formula 218]

In the formulas 211 to 218,

The definitions of X1 to X3, L, m, Ar1, Ar2, R21 to R24, r21 to r24 and Y are as defined in Formula 2.
The method according to claim 1, wherein the formula 2 is an organic light emitting device represented by any one of the following formulas 401 to 403:

[Formula 401]

[Formula 402]

[Formula 403]

In the above formulas 401 to 403,

X1 to X3, L, m, Ar1, Ar2, R21, R22, R24, r21, r22, r24 and Y are the same as defined in Formula 2,

R25 and R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r25 and r26 are the same or different from each other, and each independently an integer of 0 to 6, and when r25 is 2 or more, R25 is the same or different from each other, and when r26 is 2 or more, R26 is the same or different from each other.
The method according to claim 1, wherein the formula 1 is an organic light emitting device represented by any one of the following formulas 101 to 108:

[Formula 101]

[Formula 102]

[Formula 103]

[Formula 104]

[Formula 105]

[Formula 106]

[Formula 107]

[Formula 108]

In the formulas 101 to 108,

The definitions of X, A1 and A2 are as defined in Formula 1,

Q is O; S; Se; N(R51); Or C(R52)(R53),

R11 to R20 and R51 to R53 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

r11 and r12 are integers from 0 to 4, and when 2 or more, R11 and R12 are the same as or different from each other,

r13 is an integer from 0 to 3, and when 2 or more, R13 is the same or different from each other,

r14 to r20 are integers from 0 to 6, and when 2 or more, R14 to R20 are the same or different from each other.
The method according to claim 1,

X is B, A1 is N(R101), A2 is N(R102),

R101 and R102 are the same as or different from each other, and each independently a C1-C10 alkyl group; Or a C6-C30 aryl group substituted or unsubstituted with a C1-C10 alkyl group.
The method according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:

.
The method according to claim 1, wherein the compound represented by Formula 2 is any one selected from the following compounds:

.
The method according to claim 1, wherein the compound represented by Formula 2 is any one selected from the following compounds:

.
The method according to claim 1, wherein the compound represented by Formula 2 is any one selected from the following compounds:

.
The method according to claim 1,

The first organic material layer is an organic light emitting device that is a light emitting layer.
The method according to claim 1,

The first organic material layer is a light emitting layer, the light emitting layer comprises a dopant material, the dopant material is an organic light emitting device comprising a compound represented by the formula (1).
The method according to claim 12,

The organic light emitting device further comprises one or more light emitting layers.
The method according to claim 12,

The organic light emitting device further comprises one or more light emitting layers in which the maximum light emission peak appears in a wavelength band different from the wavelength band where the maximum light emission peak of the light emitting layer including the compound represented by Formula 1 appears.
The method according to claim 12,

The light emitting layer including the compound represented by Formula 1 further comprises a fluorescent dopant.
The method according to claim 15,

An organic light-emitting device comprising a phosphorescent dopant at least one emission layer having a maximum emission peak at a wavelength band different from a wavelength band at which the maximum emission peak of the emission layer including the compound represented by Chemical Formula 1 appears.