KR20210033434A - Organic light emitting device - Google Patents

Abstract

The present invention relates to an organic light emitting device. The organic light emitting device comprises: an anode; a cathode provided to face the anode; and a light emitting layer between the anode and the cathode. The light emitting layer includes a compound represented by a formula 1 and formula 2.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

The present application relates to an organic light emitting device. This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0114707 filed with the Korean Intellectual Property Office on September 18, 2019, all of which are incorporated herein.

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

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

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

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

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

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

Therefore, in the technical field, there is a demand for the development of organic materials having the above requirements.

Korean Patent Publication No. 2012-0112277

The present specification relates to an organic light emitting device.

The present invention is an anode; A cathode provided opposite to the anode; And an organic light emitting device provided with a light emitting layer between the anode and the cathode,

The emission layer provides an organic light-emitting device including a compound of Formula 1 and a compound of Formula 2 below.

[Formula 1]

[Formula 2]

In Formulas 1 and 2,

Ar1 is a substituted or unsubstituted aryl group,

Ar2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar3 and Ar4 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,

Ar5 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

L1 is a phenylene group; Or a naphthylene group,

L2 to L4 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

R1 and R3 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

R2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,

m is an integer from 0 to 8,

n and o are each an integer of 0 to 7,

When m to o are each 2 or more, the substituents in parentheses are the same as or different from each other,

The compounds of Formulas 1 and 2 are different from each other.

The organic light-emitting device comprising the compounds of Formula 1 and Formula 2 in the emission layer according to the present invention emits blue light, includes two different anthracene compounds as hosts, and the bonding position of the carbazole of Formula 1 is 2 Burn-in has excellent effects in terms of voltage, efficiency and life.

1 illustrates an example of an organic light-emitting device according to an exemplary embodiment of the present specification.

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

In this specification, when a member is positioned "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member exists between the two members.

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

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

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

The term “deuterated” is intended to mean that at least one available H has been replaced by D. For an X% deuterated compound or group, X% of the available H is replaced by D. Deuterated compounds or groups are those in which deuterium is present at more than 100 times the natural abundance level.

According to an exemplary embodiment of the present invention, the compound of Formula 1 is a 1% to 100% deuterated compound.

According to an exemplary embodiment of the present invention, the compound of Formula 2 is a 1% to 100% deuterated compound.

According to an exemplary embodiment of the present invention, the compounds of Formulas 1 and 2 are 1% to 100% deuterated compounds.

According to an exemplary embodiment of the present invention, the compounds of Formulas 1 and 2 are 50% to 100% deuterated compounds.

Further, according to an exemplary embodiment of the present invention, when the compounds of Formulas 1 and 2 are deuterated, the efficiency and life of the device are improved. Specifically, when hydrogen is replaced with deuterium, the chemical properties of the compound hardly change. However, since the atomic weight of deuterium is twice the atomic weight of hydrogen, the physical properties of deuterated compounds may change. For example, a compound substituted with deuterium has a lower vibrational energy level. Compounds substituted with deuterium can prevent reduction of Van der Waals force between molecules or decrease in quantum efficiency due to collisions caused by vibrations between molecules. In addition, the C-D bond can improve the stability of the compound. Accordingly, it is more preferable that the compound represented by Formula 1 or 2 contains deuterium in terms of efficiency and lifespan of the device.

Compounds of Formulas 1 and 2 including deuterium can be prepared by a known deuteration reaction. According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is formed using a deuterated compound as a precursor, or deuterium is introduced into the compound through a hydrogen-deuterium exchange reaction under an acid catalyst using a deuterated solvent. You may.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification,

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

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

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

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

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

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

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

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

In the present specification, the silyl group may be represented by the formula of _{-SiY a} Y _b Y _{c , wherein Y a} , Y _b and Y _c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto. Does not.

In the present specification, the phosphine oxide group is represented by _{-P(=O)R 101} R _{102 , R 101} and R ₁₀₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Alkyl group; Alkenyl group; Alkoxy group; Cycloalkyl group; Aryl group; And a substituent consisting of at least one of a heterocyclic group. Specifically, there are diphenylphosphine oxide group, dinaphthylphosphine oxide group, and the like, but are not limited thereto.

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

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

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

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

,

,

, 등이 될 수 있다. 다만, 이에 한정되는 것은 아니다. When the fluorenyl group is substituted,

,

,

Can be, etc. However, it is not limited thereto.

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

,

,

,

,

,

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

,

,

,

,

,

And the like, but are not limited thereto.

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

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

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

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

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

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

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

In the exemplary embodiment of the present specification, the emission layer may include the compound of Formula 1 and the compound of Formula 2 in a weight ratio of 10:1 to 1:10.

In the exemplary embodiment of the present specification, the emission layer may include the compound of Formula 1 and the compound of Formula 2 in a weight ratio of 2:1 to 1:2.

In the exemplary embodiment of the present specification, the emission layer may include the compound of Formula 1 and the compound of Formula 2 in a weight ratio of 1:1.

In the exemplary embodiment of the present specification, L1 may be selected from the following structural formulas.

In the above structural formula, a dotted line means a position bonded to the anthracene and carbazole of Formula 1, respectively.

In the exemplary embodiment of the present specification, L1 may be selected from the following structural formulas.

In the above structural formula, a dotted line means a position bonded to the anthracene and carbazole of Formula 1, respectively.

In the exemplary embodiment of the present specification, Ar1 is an aryl group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 is a phenyl group, a biphenyl group, or a naphthyl group.

In the exemplary embodiment of the present specification, Ar1 is a phenyl group.

In the exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group including O or S having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar2 is an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar2 is an aryl group having 6 to 20 carbon atoms, or a heteroaryl group including O or S having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthre. It is a nil group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

In the exemplary embodiment of the present specification, Ar2 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

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

In the exemplary embodiment of the present specification, R2 may be hydrogen or deuterium, or may be combined with an adjacent group to form a substituted or unsubstituted aromatic ring.

In the exemplary embodiment of the present specification, R2 may be hydrogen or deuterium, or may be combined with an adjacent group to form an aromatic ring.

In the exemplary embodiment of the present specification, R2 may be hydrogen or deuterium, or may be combined with an adjacent group to form a benzene ring.

In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted O or S having 2 to 30 carbon atoms. It is a containing heteroaryl group.

In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms, or a heteroaryl group including O or S having 2 to 30 carbon atoms.

,

,

,

,

또는

이다.In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted Naphthyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted Or an unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted fluorenobenzofuranyl group, a substituted or unsubstituted benzothienobenzofuranyl group,

,

,

,

,

or

to be.

,

,

,

,

또는

이다.In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a pyrenyl group, a triphenylenyl group, and a dibenzofuranyl group. Benzothiophenyl group, naphthobenzofuranyl group, fluorenobenzofuranyl group, benzothienobenzofuranyl group,

,

,

,

,

or

to be.

In the exemplary embodiment of the present specification, at least one of Ar3 and Ar4 is a substituted or unsubstituted heteroaryl group containing O or S having 2 to 30 carbon atoms.

,

,

,

,

또는

이다.In an exemplary embodiment of the present specification, at least one of Ar3 and Ar4 is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted A cyclic fluorenobenzofuranyl group, a substituted or unsubstituted benzothienobenzofuranyl group,

,

,

,

,

or

to be.

,

,

,

,

또는

이다.In an exemplary embodiment of the present specification, at least one of Ar3 and Ar4 is a dibenzofuranyl group unsubstituted or substituted with an aryl group, a dibenzothiophenyl group unsubstituted or substituted with an aryl group, a naphthobenzofuranyl group, and fluorenobenzofura. Nil group, benzothienobenzofuranyl group,

,

,

,

,

or

to be.

In the exemplary embodiment of the present specification, at least one of Ar3 and Ar4 may be represented by the following Chemical Formula 2-1, Chemical Formula 2-2, or Chemical Formula 2-3.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Formula 2-1, Formula 2-2, and Formula 2-3,

X1 is O or S,

는 상기 L2 또는 L3와 결합하는 위치를 의미하고,

Means a position bonded to the L2 or L3,

R4 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

R6 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

p is an integer of 0 to 7, and when p is an integer of 2 or more, R4 is the same as or different from each other,

q is an integer from 0 to 9, and when p is an integer of 2 or more, R5 is the same as or different from each other,

r is an integer of 0 to 3, and when r is an integer of 2 or more, R6 is the same as or different from each other,

* At least two of them are bonded to the following Chemical Formula 2-4, and the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

[Formula 2-4]

In Formula 2-4,

W is O, S or CR'R",

R'and R" are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

R7 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

s is an integer of 0 to 4, and when s is an integer of 2 or more, R7 is the same as or different from each other,

* Is a position bonded to Formula 2-3.

In the exemplary embodiment of the present specification, R4 is hydrogen, deuterium, or a phenyl group.

In the exemplary embodiment of the present specification, R'and R" are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms to be.

In the exemplary embodiment of the present specification, R'and R" are the same as or different from each other, and each independently an alkyl group having 1 to 50 carbon atoms; or an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R'and R" are the same as or different from each other, and each independently a methyl group; or a phenyl group.

In the exemplary embodiment of the present specification, L2 to L4 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.

In the exemplary embodiment of the present specification, L2 to L4 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, L2 to L4 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.

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

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

In the exemplary embodiment of the present specification, the emission layer further includes a dopant compound.

In the exemplary embodiment of the present specification, when the sum of the weight of the compound of Formula 1 and the weight of the compound of Formula 2 is 100 parts by weight, the dopant compound may be included in an amount greater than 0 to less than 10 parts by weight.

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

[Formula 3]

In Formula 3,

X10 is B or P(=O),

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

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

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

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

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

The compound represented by Formula 1 according to an exemplary embodiment of the present invention may have a core structure as shown in Scheme 1 below, and the compound represented by Formula 2 according to an exemplary embodiment of the present invention is represented by the following Schemes 2-1 and 2 A core structure may be prepared as shown in -2, and the compound represented by Formula 3 according to an exemplary embodiment of the present invention may have a core structure as shown in Scheme 3 below. Substituents of Formulas 1 to 3 prepared in Schemes 1, 2-1, 2-2 and 3 below may be bonded by methods known in the art, and the type, position, or number of substituents may be determined in the art. It can be changed according to known techniques.

<Reaction Scheme 1>

In Reaction Scheme 1, the definitions of R1, Ar1, Ar2, and L1 are as defined in Formula 1, and R11 and R12 are the same as or different from each other, and each independently, hydrogen or a substituted or unsubstituted alkyl group or bonded to each other It forms a substituted or unsubstituted ring.

<Reaction Scheme 2-1, When Ar5 in Formula 2 is hydrogen>

In Reaction Scheme 2-1, the definitions of R3, L2, L3, Ar3, and Ar4 are as defined in Chemical Formula 2, and R11 and R12 are the same as those in Scheme 1 above.

<Reaction Scheme 2-2, When Ar5 in Formula 2 is not hydrogen>

In Reaction Scheme 2-2, the definitions of R3, L2, L3, L4, Ar3, Ar4, and Ar5 are as defined in Chemical Formula 2, and R11 and R12 are the same as those in Scheme 1.

<Reaction Scheme 3>

In Reaction Scheme 3, the definitions of Cy1 to Cy3, Y1, Y2, and X10 are as defined in Chemical Formula 3.

In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents to the core structures prepared in Schemes 1, 2-1, 2-2, and 3 above. In addition, in the present specification, the HOMO and LUMO energy levels of the compound may be adjusted by introducing various substituents to the core structure having the above structure.

The organic light-emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except for forming a light-emitting layer using the compounds represented by Formulas 1, 2, and 3 described above.

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

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

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

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

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

According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

The organic light-emitting device may have, for example, a stacked structure as described below, but is not limited thereto.

(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/electron blocking layer/light emitting layer/electron transport layer/cathode

(8) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode

(9) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode

(10) Anode/Hole injection layer/Hole transport layer/Electron blocking layer/Light emitting layer/Electron transport layer/Electron injection layer/Cathode

(11) Anode/Hole Transport Layer/Light-Emitting Layer/Hole Blocking Layer/Electron Transport Layer/Cathode

(12) Anode/Hole transport layer/Light emitting layer/Hole blocking layer/Electron transport layer/Electron injection layer/Cathode

(13) Anode/Hole injection layer/Hole transport layer/Light emitting layer/Hole blocking layer/Electron transport layer/Cathode

(14) Anode/Hole injection layer/Hole transport layer/Light emitting layer/Hole blocking layer/Electron transport layer/Electron injection layer/Cathode

(15) Anode/Hole Injection Layer/Hole Transport Layer/Electron Suppression Layer/Emitting Layer/Hole Suppression Layer/Layer for Simultaneous Electron Transport and Electron Injection/Cathode

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

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

1 illustrates an organic light emitting device and is not limited thereto.

The organic light emitting device of the present specification includes an organic material layer including an emission layer, and the emission layer includes a compound represented by Formula 1, a compound represented by Formula 2, and a compound represented by Formula 3.

According to an exemplary embodiment of the present specification, the emission layer of the organic light emitting device includes a compound represented by Formula 1 and a compound represented by Formula 2 as a host of the emission layer, and the compound represented by Formula 3 is used as the emission layer. Include as a dopant of.

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

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

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

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

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

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

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

The cathode material is generally preferably a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

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

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

As the light-emitting material, a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.

When the organic light-emitting device includes an additional light-emitting layer in addition to the light-emitting layer including the compound represented by Formulas 1, 2 and 3 described above, the additional light-emitting layer may emit red, green or blue light, and a phosphorescent material or a fluorescent material It can be made of. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The host material of the additional light-emitting layer includes a condensed aromatic ring derivative or a heterocyclic-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives and the like, but are not limited thereto. In addition, a polymer compound may be used, and a polymer compound such as poly-1,4-phenylene or polyfluorene may be used, but is not limited thereto.

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

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer.As an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Do. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq _3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.

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

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

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

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

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

1. Synthesis of compound 1

Synthesis Example 1-1. Synthesis of compound 1-a

2-Bromo-9-phenyl-9H-carbazole (50 g, 155 mmol) and (3-chlorophenyl) boronic acid (24 g, 155 mmol) were added to a round bottom flask and tetrahydrofuran (THF) 800 ml Melted in. Potassium carbonate (43 g, 310 mmol) was dissolved in 200 ml of distilled water and added, and tetrakis(triphenylphosphine)palladium(0) (TTP, 9.0g, 7.7 mmol) was added. After refluxing for 2 hours and cooling, the organic layer was separated. After distillation under reduced pressure to remove tetrahydrofuran (THF), it was dissolved in chloroform, placed in a separatory funnel, and washed several times with water. Magnesium sulfate was added to the organic layer to remove water, and then filtered. The filtrate was distilled under reduced pressure to remove the solvent. Purified using column chromatography to obtain compound 1-a. (40 g, 73% yield)

Synthesis Example 1-2. Synthesis of compound 1-b

Compound 1-a (40 g,113 mmol), bis(pinacolato)diborone (43 g, 170 mmol) and potassium acetate (KOAc, 27.7 g, 283 mmol) were added to a flask together with 300 ml of Dioxane to disperse. After adding bis(dibenzylideneacetone)palladium (Pd(dba) _2, 0.65g, 1.1mmol) and tricyclohexylphosphine (PCy3, 0.63g, 2.3mmol), the mixture was stirred under reflux for 24 hours. After completion of the reaction, Dioxane was removed by distillation under reduced pressure. After dissolving in chloroform, extraction was performed three times with distilled water, the organic layer was distilled under reduced pressure to remove chloroform, and then purified by column chromatography to obtain compound 1-b. (38 g, yield 75%)

Synthesis Example 1-3. Synthesis of compound 1

After dissolving 9-bromo-10-phenylanthracene (25 g, 75 mmol) and compound 1-b (35 g, 79 mmol) in Dioxane (400 ml), potassium carbonate (21 g, 150 mmol) was added to 100 ml of distilled water. After melting and adding, bis(tri-tert-butylphosphine)palladium(0) (BTP, 0.076 g, 0.15 mmol) was added and stirred under reflux for 24 hours. The reaction solution was cooled, the organic layer was extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and purified using column chromatography to obtain compound 1 (19g, yield 75%). [M+H ⁺ ]= 572.3

2. Synthesis of compound 2

Synthesis Example 2-1. Synthesis of compound 2-a

Compound 2-a was synthesized in the same manner as in Synthesis Example 1-1, except that (4-chlorophenyl) boronic acid was used instead of (3-chlorophenyl) boronic acid.

Synthesis Example 2-2. Synthesis of compound 2-b

Compound 2-b was synthesized in the same manner as in Synthesis Example 1-2, except that compound 2-a was used instead of compound 1-a.

Synthesis Example 2-3. Synthesis of compound 2

Compound 2 was synthesized in the same manner as in Synthesis Example 1-3, except that 2-b was used instead of compound 1-b. [M+H ⁺ ]= 572.3

3. Synthesis of compound 3

Synthesis Example 3-1. Synthesis of compound 3

Compound 1 (10g) and AlCl ₃ (2g) were _{added to C 6} D ₆ (200ml) and stirred for 2 hours. After completion of the reaction, D ₂ O (15ml) was added and stirred for 30 minutes, and then trimethylamine (1.2ml) was added dropwise. The reaction solution was transferred to a separatory funnel, and extracted with water and toluene. The extract _{was dried over MgSO 4} and recrystallized with ethyl acetate to obtain compound 3. [M+H ⁺ ]=601.9

4. Synthesis of compound 4

Synthesis Example 4-1. Synthesis of compound 4

Compound 4 was synthesized in the same manner except that 2-(10-bromoanthracene-9-yl)dibenzo[b,d]furan was used instead of 9-bromo-10-phenylanthracene in Synthesis Example 1-3. Synthesized. [M+H ⁺ ]= 562.3

5. Synthesis of compound 5

Synthesis Example 5-1. Synthesis of compound 5-a

In Synthesis Example 1-1, instead of 2-bromo-9-phenyl-9H-carbazole and (3-chlorophenyl) boronic acid, (9-phenyl-9H-carbazol-2-yl) boronic acid and 2-bromo- Compound 5-a was synthesized by the same synthesis except that 7-chloronaphthalene was used.

Synthesis Example 5-2. Synthesis of compound 5-b

In Synthesis Example 1-2, compound 5-b was synthesized in the same manner, except that compound 5-a was used instead of compound 1-a.

Synthesis Example 5-3. Synthesis of compound 5

Compound 5 was synthesized in the same manner as in Synthesis Example 1-3 except that compound 5-b was used instead of 1-b. [M+H ⁺ ]= 622.8

6. Synthesis of compound 6

Synthesis Example 6-1. Synthesis of compound 6-a

Instead of 2-bromo-9-phenyl-9H-carbazole and (3-chlorophenyl) boronic acid in Synthesis Example 1-1, (4-chlorophenyl) boronic acid and 2-bromodibenzo[b,d] furan were used. Except for the synthesis, compound 6-a was synthesized in the same manner.

Synthesis Example 6-2. Synthesis of compound 6-b

In Synthesis Example 1-2, compound 6-b was synthesized in the same manner, except that compound 6-a was used instead of compound 1-a.

Synthesis Example 6-3. Synthesis of compound 6

In Synthesis Example 1-3, compound 1-b and 9-bromo-10-phenylanthracene instead of 6-b and 9-bromo-10-(naphthalen-1-yl) anthracene were synthesized in the same manner, except that Compound 6 was synthesized. [M+H ⁺ ]= 547.2

7. Synthesis of compound 7

Synthesis Example 7-1. Synthesis of compound 7-a

In Synthesis Example 3-1, compound 7-a was obtained by the same synthesis except that 9-(naphthalene-1-yl)anthracene was used instead of compound 1.

Synthesis Example 7-2. Synthesis of compound 7-b

After dissolving compound 7-a (30g, 94mmol) in 400ml of dimethylformamide (DMF), N-bromosuccinimide (NBS, 16.7g, 94mmol) dissolved in 50ml of DMF is slowly added dropwise. After stirring at room temperature for 2 hours, 500 ml of water was added dropwise. When a solid is formed, it is filtered, dissolved in chloroform, and extracted several times with distilled water. Recrystallized from ethyl acetate to obtain compound 7-b. (25g, yield 68%)

Synthesis Example 7-3. Synthesis of compound 7

Compound 7 was synthesized in the same manner as in Synthesis Example 1-3, except that 6-b and 7-b were used instead of compounds 1-b and 9-bromo-10-phenylanthracene. [M+H ⁺ ]= 562.8

8. Synthesis of compound 8.

Synthesis Example 8-1. Synthesis of compound 8

Instead of compound 1-b and 9-bromo-10-phenylanthracene in Synthesis Example 1-3, 4,4,5,5,-tetramethyl-2-(3-(naphthalen-1-yl)phenyl)-1, Compound 8 was synthesized in the same manner, except that 3,2-dioxaborolein and 9-(10-bromoanthracene-9-yl)dibenzo[b,d]furan were used. [M+H ⁺ ]= 547.2

9. Synthesis of compound 9

Synthesis Example 9-1. Synthesis of compound 9-a

In Synthesis Example 1-1, instead of 2-bromo-9-phenyl-9H-carbazole and (3-chlorophenyl) boronic acid, (10-(naphthalen-1-yl) anthracene-9-yl) boronic acid and 8-bro Compound 9-a was synthesized in the same manner except that mo-1-chlorodibenzo[b,d]furan was used.

Synthesis Example 9-2. Synthesis of compound 9

Compound 9 was synthesized in the same manner as in Synthesis Example 1-3, except that 2-naphthylboronic acid and compound 9-a were used instead of compound 1-b and 9-bromo-10-phenylanthracene. [M+H ⁺ ]= 597.3

10. Synthesis of compound 10

Synthesis Example 10-1. Synthesis of compound 10-a

Compound 10 was synthesized in the same manner as in Synthesis Example 1-1 except that 2-bromoanthracene and phenylboronic acid were used instead of 2-bromo-9-phenyl-9H-carbazole and (3-chlorophenyl) boronic acid. -a was synthesized.

Synthesis Example 10-2. Synthesis of compound 10-b

Compound 10-b was synthesized in the same manner as in Synthesis Example 7-2, except that compound 10-a was used instead of compound 7-a.

Synthesis Example 10-3. Synthesis of compound 10-c

Compound 10-c was synthesized in the same manner as in Synthesis Example 1-3, except that phenylboronic acid and compound 10-b were used instead of compounds 1-b and 9-bromo-10-phenylanthracene.

Synthesis Example 10-4. Synthesis of compound 10-d

In Synthesis Example 7-2, compound 10-d was synthesized in the same manner, except that compound 10-c was used instead of compound 7-a.

Synthesis Example 10-5. Synthesis of compound 10

Compound 10 was synthesized in the same manner as in Synthesis Example 1-3, except that 10-d and 6-d were used instead of compounds 1-b and 9-bromo-10-phenylanthracene. [M+H ⁺ ]= 573.2

11. Synthesis of compound 11

Synthesis Example 11-1. Synthesis of compound 11

In Synthesis Example 1-3, instead of compound 1-b and 9-bromo-10-phenylanthracene (4-(naphthalen-2-yl)phenyl)boronic acid and 9-bromo-10-(naphthalen-1-yl)anthracene Compound 11 was synthesized by the same synthesis except for using. [M+H ⁺ ]= 507.2

12. Synthesis of compound 12

Synthesis Example 12-1. Synthesis of compound 12

Compound 12 was obtained by the same synthesis except that compound 11 was used instead of compound 1 in Synthesis Example 3-1. [M+H ⁺ ]= 533.4

13. Synthesis of compound 13

Synthesis Example 13-1. Synthesis of compound 13-a

Compound 13-a was synthesized in the same manner as in Synthesis Example 1-1, except that 2-bromonaphthalene was used instead of 2-bromo-9-phenyl-9H-carbazole.

Synthesis Example 13-2. Synthesis of compound 13-b

In Synthesis Example 1-2, compound 13-b was synthesized in the same manner, except that 13-a was used instead of compound 1-a.

Synthesis Example 13-3. Synthesis of compound 13

In Synthesis Example 1-3, instead of compound 1-b and 9-bromo-10-phenylanthracene, 13-b and 9-([1,1'-biphenyl]-4-yl)-10-bromoanthracene were used. Except for the synthesis, compound 13 was synthesized in the same manner. [M+H ⁺ ]= 533.3

14. Synthesis of compound 14

Synthesis Example 14-1. Synthesis of compound 14-a

Compound 14-a was synthesized in the same manner as in Synthesis Example 1-1, except that 1-bromopyrene was used instead of 2-bromo-9-phenyl-9H-carbazole.

Synthesis Example 14-2. Synthesis of compound 14-b

Compound 14-b was synthesized in the same manner as in Synthesis Example 1-2, except that 14-a was used instead of compound 1-a.

Synthesis Example 14-3. Synthesis of compound 14

Compound 14 was synthesized in the same manner as in Synthesis Example 1-3, except that 14-b was used instead of compound 1-b. [M+H ⁺ ]= 531.2

15. Synthesis of compound 15

Synthesis Example 15-1. Synthesis of compound 15-a

Synthesis in the same manner as in Synthesis Example 1-1 except for using 2-bromoanthracene and 1-naphthylboronic acid instead of 2-bromo-9-phenyl-9H-carbazole and (3-chlorophenyl) boronic acid Thus, compound 15-a was synthesized.

Synthesis Example 15-2. Synthesis of compound 15-b

In Synthesis Example 7-2, compound 15-b was synthesized in the same manner, except that compound 15-a was used instead of compound 7-a.

Synthesis Example 15-3. Synthesis of compound 15-c

In Synthesis Example 1-3, compound 15-c was synthesized in the same manner, except that phenylboronic acid and compound 15-b were used instead of compound 1-b and 9-bromo-10-phenylanthracene.

Synthesis Example 15-4. Synthesis of compound 15-d

Compound 15-d was synthesized in the same manner as in Synthesis Example 7-2, except that compound 15-c was used instead of compound 7-a.

Synthesis Example 15-5. Synthesis of compound 15

In Synthesis Example 1-3, compound 15 was synthesized in the same manner except that (4-(naphthalen-2-yl)phenyl)boronic acid and 15-d were used instead of compound 1-b and 9-bromo-10-phenylanthracene. Was synthesized. [M+H ⁺ ]= 583.3

16. Synthesis of compound 16

Synthesis Example 16-1. Synthesis of compound 16

Compound 16 was obtained by the same synthesis except that compound 15 was used instead of compound 1 in Synthesis Example 3-1. [M+H ⁺ ]= 613.4

17. Synthesis of compound 17

Synthesis Example 17-1. Synthesis of compound 17

In Synthesis Example 1-3, instead of compound 1-b and 9-bromo-10-phenylanthracene, naphtho[2,1-b]benzofuran-10ylboronic acid and 9-bromo-10-(naphthalen-1-yl ) Except for the use of anthracene was synthesized in the same manner to synthesize compound 17. [M+H ⁺ ]= 521.3

18. Synthesis of compound 18

Synthesis Example 18-1. Synthesis of compound 18

Synthesis in the same manner as in Synthesis Example 1-3 except that naphtho[2,1-b]benzofuran-10ylboronic acid and compound 7-b were used instead of compound 1-b and 9-bromo-10-phenylanthracene Thus, compound 18 was synthesized. [M+H ⁺ ]= 536.3

19. Synthesis of compound 19

Synthesis Example 19-1. Synthesis of compound 19

In Synthesis Example 1-3, instead of compound 1-b and 9-bromo-10-phenylanthracene, naphtho[1,2-b]benzofuran-7ylboronic acid and 9-([1,1'-biphenyl]- Compound 19 was synthesized by the same synthesis except that 3-yl)-10-bromoanthracene was used. [M+H ⁺ ]= 547.2

20. Synthesis of compound 20

Synthesis Example 20-1. Synthesis of compound 20

In Synthesis Example 1-3, instead of compound 1-b and 9-bromo-10-phenylanthracene, naphtho[2,3-b]benzofuran-2ylboronic acid and 9-bromo-10-(naphthalen-2-yl ) Compound 20 was synthesized by the same synthesis except that anthracene was used. [M+H ⁺ ]= 521.6

21. Synthesis of compound 21

Synthesis Example 21-1. Synthesis of compound 21

In Synthesis Example 1-3, compound 1-b and 9-bromo-10-phenylanthracene instead of naphtho[2,3-b]benzofuran-2ylboronic acid and 10-d were synthesized in the same manner, except that Compound 20 was synthesized. [M+H ⁺ ]= 547.2

22. Synthesis of compound 22

Synthesis Example 22-1. Synthesis of compound 22-a

After dissolving dibenzo[b,d]furan-2-ol (50g, 271mmol) in 1500ml of DMF, the temperature was lowered to 0 degrees. N-bromosuccinimide (48.3g, 271mmol) dissolved in 50ml of DMF is slowly added dropwise. After stirring for 2 hours, 500 ml of water was added dropwise. When a solid is formed, it is filtered, dissolved in chloroform, and extracted several times with distilled water. Purified by column chromatography to obtain compound 22-a. (47g, yield 65%)

Synthesis Example 22-2. Synthesis of compound 22-b

Compound 22-a (47 g, 179 mmol) and (5-chloro-2-fluorophenyl) boronic acid (31 g, 179 mmol) were placed in a round bottom flask and dissolved in 900 ml of tetrahydrofuran (THF). Potassium carbonate (49 g, 357 mmol) was dissolved in 200 ml of distilled water and added, and tetrakis(triphenylphosphine)palladium(0) (4.1 g, 3.6 mmol) was added. After refluxing for 2 hours and cooling, the organic layer was separated. After distillation under reduced pressure to remove tetrahydrofuran (THF), it was dissolved in chloroform, placed in a separatory funnel, and washed several times with water. Magnesium sulfate was added to the organic layer to remove water, and then filtered. The filtrate was distilled under reduced pressure to remove the solvent to obtain a liquid compound 22-b. (40 g, 72% yield)

Synthesis Example 22-3. Synthesis of compound 22-c

22-b (40 g, 128 mmol), potassium carbonate (53 g, 384 mmol) and 600 ml of DMF were placed in a round bottom flask and stirred under reflux for 3 hours. After cooling, the reaction solution is poured into 1.5 L of distilled water. When a solid precipitated, it was filtered. After dissolving in 750 ml of chloroform, it was washed several times with distilled water using a separatory funnel. Magnesium sulfate was added to the organic layer to remove water and filtered. Purified using column chromatography to obtain compound 22-c. (25 g, 67% yield)

Synthesis Example 22-4. Synthesis of compound 22-d

Compound 22-d was synthesized in the same manner as in Synthesis Example 1-2 except that 22-c was used instead of compound 1-a.

Synthesis Example 22-5. Synthesis of compound 22

Synthesis in the same manner as in Synthesis Example 1-3 except that compounds 22-d and 9-bromo-10-(naphthalen-1-yl)anthracene were used instead of compounds 1-b and 9-bromo-10-phenylanthracene Thus, compound 22 was synthesized. [M+H ⁺ ]= 561.2

23. Synthesis of compound 23

Synthesis Example 23-1. Synthesis of compound 23

Compound 23 was synthesized in the same manner as in Synthesis Example 1-3, except that Compound 22-d and Compound 7-b were used instead of Compound 1-b and 9-bromo-10-phenylanthracene. [M+H ⁺ ]= 576.3

24. Synthesis of compound 24

Synthesis Example 24-1. Synthesis of compound 24-a

Compound 24-a was obtained in the same manner as in Synthesis Example 22-2, except that (4-chloro-2-fluorophenyl) boronic acid was used instead of (5-chloro-2-fluorophenyl) boronic acid.

Synthesis Example 24-2. Synthesis of compound 24-b

Compound 24-b was obtained by the same synthesis except that compound 24-a was used instead of compound 22-b in Synthesis Example 22-3.

Synthesis Example 24-3. Synthesis of compound 24-c

In Synthesis Example 1-2, compound 24-c was synthesized in the same manner, except that compound 24-b was used instead of compound 1-a.

Synthesis Example 24-4. Synthesis of compound 24

Synthesis in the same manner as in Synthesis Example 1-3 except that compounds 24-c and 9-bromo-10-(naphthalen-1-yl)anthracene were used instead of compounds 1-b and 9-bromo-10-phenylanthracene. Thus, compound 24 was synthesized. [M+H ⁺ ]= 561.2

25. Synthesis of compound 25

Synthesis Example 25-1. Synthesis of compound 25-a

In Synthesis Example 22-2, instead of compound 22-a and (5-chloro-2-fluorophenyl) boronic acid, 3-bromo-2-fluorodibenzo[b,d]furan and (2-chloro-6-hydro) Compound 25-a was obtained by the same synthesis except that oxyphenyl) boronic acid was used.

Synthesis Example 25-2. Synthesis of compound 25-b

Compound 25-b was obtained in the same manner as in Synthesis Example 22-3, except that compound 25-a was used instead of compound 22-b.

Synthesis Example 25-3. Synthesis of compound 25-c

Compound 25-c was synthesized in the same manner as in Synthesis Example 1-2, except that compound 25-b was used instead of 1-a.

Synthesis Example 25-4. Synthesis of compound 25

Instead of compounds 1-b and 9-bromo-10-phenylanthracene in Synthesis Example 1-3, compounds 25-c and 9-([1,1'-biphenyl]-3-yl)-10-bromoanthracene were used. Compound 25 was synthesized in the same manner except for using. [M+H ⁺ ]= 587.2

<Experimental Example>

The structures of the compounds used in the following Examples and Comparative Examples are as follows, and among the following structures, compounds corresponding to Formulas 1 and 2 of the present invention were prepared through the aforementioned Synthesis Examples, respectively.

Example 1

A glass substrate coated with a thin film of 150 nm indium tin oxide (ITO) was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using nitrogen plasma, the substrate was transported to a vacuum evaporator. The HAT-CN compound was thermally vacuum deposited to a thickness of 5 nm on the prepared ITO transparent electrode to form a hole injection layer. Subsequently, HTL1 was thermally vacuum evaporated to a thickness of 100 nm, and HTL2 was thermally vacuum evaporated to a thickness of 10 nm to form a hole transport layer. Subsequently, compound 1 and compound 6 as a host and BD-1 (weight ratio 47.5: 47.5: 5) as a dopant were simultaneously vacuum-deposited to form a light emitting layer having a thickness of 20 nm. Then, ETL was vacuum-deposited to a thickness of 20 nm to form an electron transport layer. Then, LiF was vacuum-deposited to a thickness of 0.5 nm to form an electron injection layer. Then, aluminum was deposited to a thickness of 100 nm to form a cathode to manufacture an organic light emitting device.

Examples 2 to 40 Comparative Examples 1 to 15

An organic light emitting device was manufactured in the same manner as in Example 1, but using the materials and contents (parts by weight based on the sum of host and dopant 1) in Table 1 below as a host and a dopant. to 40 and Comparative example 1 were measured for the drive voltage (Vop) and luminous efficiency (Cd / a) at a current density of 10 mA / cm ² of the organic light-emitting device manufactured by to 15, at a current density of 20 mA / cm ² The time (LT) to become 97% of the initial luminance was measured, and the results are shown in Table 2 below.

[Table 1]

[Table 2]

From Table 2, the organic light-emitting devices of Examples 1 to 40 including both the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 herein are Comparative Examples 1 to 4 not including the compound represented by Chemical Formula 2 And it can be seen that the device has superior device characteristics than Comparative Examples 5 to 9 which do not include the compound represented by Formula 1 herein.

In addition, it can be seen that Comparative Examples 10 to 15 including compounds A and B having different positions of the substituted carbazole in Chemical Formula 1 and the compounds represented by Chemical Formula 2 are inferior in device characteristics.

101: substrate
201: anode
301: light emitting layer
401: cathode

Claims (11)

Anode; A cathode provided opposite to the anode; And an organic light-emitting device provided with a light-emitting layer between the anode and the cathode,
The emission layer is an organic light-emitting device comprising a compound of Formula 1 and a compound of Formula 2 below:
[Formula 1]

[Formula 2]

In Formulas 1 and 2,
Ar1 is a substituted or unsubstituted aryl group,
Ar2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar3 and Ar4 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,
Ar5 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L1 is a phenylene group; Or a naphthylene group,
L2 to L4 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
R1 and R3 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 heteroaryl group,
R2 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,
m is an integer from 0 to 8,
n and o are each an integer of 0 to 7,
When m to each o is 2 or more, the substituents in parentheses are the same as or different from each other,
The compounds of Formulas 1 and 2 are different from each other. The organic light-emitting device of claim 1, wherein the emission layer further comprises a dopant compound. The organic light-emitting device of claim 1, wherein the emission layer comprises the compound of Formula 1 and the compound of Formula 2 in a weight ratio of 10:1 to 1:10. The organic light emitting device of claim 2, wherein the dopant compound is represented by the following formula (3):
[Formula 3]

In Formula 3,
X10 is B or P(=O),
Y1 is O, S or NRa, Y2 is O, S or NRb,
Cy1 to Cy3 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,
Ra is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with Cy1 or Cy3 to form a substituted or unsubstituted ring,
Rb is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with Cy2 or Cy3 to form a substituted or unsubstituted ring. The organic light-emitting device of claim 2, wherein when the sum of the weight of the compound of Formula 1 and the weight of the compound of Formula 2 is 100 parts by weight, the dopant compound is included in an amount greater than 0 to less than 10 parts by weight. The organic light-emitting device of claim 1, wherein at least one of Ar3 and Ar4 is represented by the following Chemical Formula 2-1, Chemical Formula 2-2, or Chemical Formula 2-3:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Formula 2-1, Formula 2-2, and Formula 2-3,
X1 is O or S,

Means a position bonded to the L2 or L3,
R4 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
R6 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
p is an integer of 0 to 7, and when p is an integer of 2 or more, R4 is the same as or different from each other,
q is an integer from 0 to 9, and when p is an integer of 2 or more, R5 is the same as or different from each other,
r is an integer of 0 to 3, and when r is an integer of 2 or more, R6 is the same as or different from each other,
* At least two of them are bonded to the following Chemical Formula 2-4, and the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
[Formula 2-4]

In Formula 2-4,
W is O, S or CR'R",
R7 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
R'and R" are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
s is an integer of 0 to 3, and when s is an integer of 2 or more, R7 is the same as or different from each other,
* Is a position bonded to Formula 2-3. The organic light-emitting device of claim 1, wherein the compound of Formula 1 is selected from the following structural formulas:

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

The organic light-emitting device of claim 4, wherein the compound of Formula 3 is selected from the following structural formulas:

The organic light-emitting device of claim 1, wherein the compound of Formula 1 is deuterated by 1% to 100%. The organic light-emitting device of claim 1, wherein the compound of Formula 2 is deuterated by 1% to 100%.

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