KR20200033770A - Organic light emitting device - Google Patents

Abstract

The present specification relates to an organic light emitting device comprising: an anode; a cathode; a light emitting layer disposed between the anode and the cathode; and an organic material layer disposed between the cathode and the light emitting layer, wherein the light emitting layer includes a compound represented by Formula 1, and the organic material layer disposed between the cathode and the light emitting layer includes a compound represented by Formula 2.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

The present invention relates to an organic light emitting device in which the light emitting layer includes a compound represented by Formula 1, and the organic material layer provided between the light emitting layers includes a compound represented by Formula 2.

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0112966, filed with the Korean Intellectual Property Office on September 20, 2018, all of which is 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, the organic material layer is formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, or an electron injection layer. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, electrons are injected at the cathode, and excitons are formed when the injected holes meet the electrons. It glows when it falls to the ground.

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

Patent Publication No. 10-2008-0103953

In the present invention, the light emitting layer includes a compound represented by the formula (1), and the organic material layer provided between the cathode and the light emitting layer includes the compound represented by the formula (2), so that the driving voltage is low, high in efficiency, excellent in life characteristics, or color purity. It is intended to provide a high organic light emitting device.

An exemplary embodiment of the present specification is an anode; cathode; A light emitting layer provided between the anode and the cathode; And an organic material layer provided between the cathode and the light emitting layer, wherein the light emitting layer includes a compound represented by Formula 1 below, and the organic material layer provided between the cathode and the light emitting layer represents Formula 2 below. It provides an organic light-emitting device comprising a compound.

[Formula 1]

In Chemical Formula 1,

Any one of R1 to R8 is a group connected to any one of Ar1 or R11 to R18, one is a group connected to any one of R11 to R18, and the rest are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; -OR; -SiRaRbRc; -OSiRaRbRc; Or a substituted or unsubstituted aryl group,

Any one of R11 to R18 is a group connected to any one of Ar2 or R1 to R8, one is a group connected to any one of R1 to R8, and the rest are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; -OR; -SiRaRbRc; -OSiRaRbRc; Or a substituted or unsubstituted aryl group,

R and Ra to Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl groups; Or an aryl group,

Ar1 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group,

Ar2 is a substituted or unsubstituted aryl group,

n is an integer from 1 to 3,

The compound represented by Formula 1 includes at least one deuterium,

[Formula 2]

In Chemical Formula 2,

HAr is a substituted or unsubstituted nitrogen-containing heterocyclic group,

L is a direct bond; -O-; A substituted or unsubstituted divalent to tetravalent aryl group; Or a substituted or unsubstituted divalent to tetravalent heteroaryl group,

L1 and L2 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,

a1 is an integer from 0 to 3, and when a1 is 2 or more, L1 is the same or different from each other, b1 is an integer from 0 to 3, and when b1 is 2 or more, L2 is the same or different from each other,

a is 1 or 2, b is 1 or 2, and when b is 2, HAr is the same or different from each other,

a2 is 1 or 2, b2 is 1 or 2,

When a2 is 2,-[(L1) _a1- (CN) _a ] is the same as or different from each other,

When b2 is 2,-[(L2) _b1- (HAr) _b ] is the same as or different from each other.

The organic light emitting diode according to the exemplary embodiment of the present specification has an effect of having a low driving voltage, high efficiency, excellent life characteristics, or high color purity.

1 to 3 schematically show the structure of an organic light emitting device according to an exemplary embodiment of the present invention.

Hereinafter, the present invention 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.

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

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

In the present specification, terms such as 'include' or 'have' mean that a feature or component described in the specification exists, and excludes the possibility of adding one or more other features or components in advance. It is not.

In the present specification, when a part such as a region or a layer is provided on or on another part, it includes not only the case directly above the other part, but also the case where other areas, layers, and the like are interposed therebetween.

In this specification, "deuteration" means that hydrogen is replaced with deuterium. The meaning that a compound is "deuterated" means that one or more hydrogens present in the compound have been replaced with deuterium. X% deuterated compound or group means that X% of available hydrogen is replaced with deuterium.

In the present specification, the deuterated ratio of a compound means a ratio occupied by the number of deuterium among the sum of the number of hydrogen and deuterium present in the compound.

In the present specification, when all the hydrogens that may be present in the compound are substituted with deuterium, it is indicated that it is 100% deuterated.

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

In the present specification, an alkyl group means a straight chain or branched chain saturated hydrocarbon. The number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. The alkyl group may be chained or cyclic.

Specific examples of the chained alkyl group are methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, n-pentyl, isopentyl, neopentyl , n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 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, etc., but is not limited thereto. Does not work.

The number of carbon atoms of the cyclic alkyl group (cycloalkyl group) is not particularly limited, and the number of carbon atoms of the cyclic alkyl group (cycloalkyl group) is preferably 3 to 40. According to an exemplary embodiment, the cycloalkyl group has 3 to 24 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 14 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 8 carbon atoms. Specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethyl Cyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.

In the present specification, the alkenyl group represents a linear or pulverized unsaturated hydrocarbon group, and may be a straight chain or a branched chain. The number of carbon atoms is not particularly limited, but is preferably 2 to 30. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. Specific examples include, but are not limited to, ethenyl, vinyl, propenyl, allyl, isopropenyl, butenyl, isobutenyl, n-pentenyl and n-hexenyl.

In the present 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 are planar, and a derivative in an aromatic hydrocarbon is a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed with an aromatic hydrocarbon or an aromatic hydrocarbon. It means a structure with similar properties. In addition, in the present specification, an aryl group includes a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are connected to each other. According to one embodiment, the carbon number of the aryl group is 6 to 36, 6 to 30, or 6 to 25. According to one embodiment, the carbon number of the aryl group is 6 to 18. According to one embodiment, the carbon number of the aryl group is 6 to 13.

The aryl group may be monocyclic or polycyclic. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and a quarterphenyl group, but are not limited thereto. The polycyclic aryl group is a naphthyl group, anthracenyl group, phenanthrenyl group, perillynyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, tetrasenyl group, chrysenyl group, fluorenyl group, indenyl group, Acenaphthyl group, benzofluorenyl group, and the like, but are not limited thereto.

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 spiro bond with 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 heterocyclic group means a monovalent heterocycle. The heterocycle is an aromatic heterocycle; Or it may be an aliphatic heterocycle. In one embodiment, the number of carbon atoms in the heterocycle is not particularly limited, but is preferably 2 to 40 carbon atoms. According to an exemplary embodiment, the heterocycle has 2 to 30 carbon atoms. According to another exemplary embodiment, the heterocycle has 2 to 20 carbon atoms.

In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms. Examples of the aliphatic heterocycle include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepan, and azocaine , Thiokane, and the like.

In the present specification, an aromatic heterocycle means an aromatic ring containing one or more of heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isooxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinazoline, quinoxaline, naphthyridine, acridine, phenan Tridine, diazanaphthalene, driazainden, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole , Dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, phenanthridine, indolocarbazole, indenocarbazole, and the like, but is not limited thereto.

In the present specification, a heteroaryl group means a monovalent aromatic heterocycle.

In the present specification, the description of the aryl group can be applied, except that the arylene group is divalent.

In the present specification, a description of the heteroaryl group may be applied, except that the heteroarylene group is divalent.

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

An exemplary embodiment of the present specification is an anode; cathode; A light emitting layer provided between the anode and the cathode; And an organic material layer provided between the cathode and the light emitting layer, wherein the light emitting layer includes a compound represented by Formula 1, and the organic material layer provided between the cathode and the light emitting layer is represented by Formula 2 It provides an organic light-emitting device comprising a compound.

In one embodiment, the compound represented by Formula 1 includes at least one deuterium. When hydrogen is replaced with deuterium, the chemical properties of the compounds change little. However, since the atomic weight of deuterium is twice that of hydrogen, the deuterated compound may change its physical properties. For example, a compound substituted with deuterium has a low vibration energy level. Reduction of the vibration energy level can prevent a decrease in the intermolecular van der Waals force or a reduction in the quantum efficiency due to collision due to intermolecular vibration. Accordingly, the compound represented by Chemical Formula 1 may include deuterium to improve the efficiency and lifetime of the device.

The compound represented by Chemical Formula 2 includes nitrogen-containing heterocycle and CN .

The nitrogen-containing heterocycle, which is generally used as an electron injection and transport material, has excellent electron injection and transfer capability. This may cause an excessively large amount of electrons to pass to the emission layer, resulting in an imbalance between holes and electrons in the emission layer. In addition, in the light-emitting region, excitons formed by electron-hole pairs are accumulated at the interface between the hole transport layer and the light-emitting layer, which causes a decrease in efficiency and life of the device.

Since the compound represented by Chemical Formula 2 of the present invention has a strong electron acceptor substituent, such as CN, is introduced into a nitrogen-containing heterocycle, the LUMO (Lowest Unoccupied Molecular Orbital) of the compound decreases and at the same time increases the dipole moment. As a result, the movement speed of electrons passing to the light emitting layer is controlled, thereby improving the efficiency and life of the device.

Hereinafter, an exemplary embodiment of the compound represented by Chemical Formula 1 will be described.

The compound represented by Chemical Formula 1 is deuterated at least 10% according to an exemplary embodiment, deuterated at least 20% according to an exemplary embodiment, and deuterated at least 30% according to an exemplary embodiment, according to an exemplary embodiment More than 40% deuterated, according to one embodiment more than 50% deuterated, according to one embodiment more than 60% deuterated, according to one embodiment more than 70% deuterated, 80% according to one embodiment The above is deuterated, and according to one embodiment, 90% or more is deuterated, and according to one embodiment, it is 100% deuterated.

According to the exemplary embodiment of the present specification, Ar1 is hydrogen; heavy hydrogen; Or an aryl group unsubstituted or substituted with R21.

According to an exemplary embodiment of the present specification, R21 is deuterium; Cyano group; Alkyl groups; Alkenyl group; -ORd; -SiReRfRg; -OSiReRfRg; Or an aryl group, the Rd to Rg are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl groups; Or an aryl group.

According to an exemplary embodiment of the present specification, R21 is deuterium; Cyano group; Or an alkyl group.

According to the exemplary embodiment of the present specification, Ar1 is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted quarterphenyl group; A substituted or unsubstituted naphthylphenyl group; A substituted or unsubstituted naphthylbiphenyl group; A substituted or unsubstituted phenylnaphthyl group; A substituted or unsubstituted naphthyl naphthyl group; Or a substituted or unsubstituted biphenyl naphthyl group.

According to the exemplary embodiment of the present specification, Ar1 is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with deuterium or cyano groups; A biphenyl group unsubstituted or substituted with deuterium or cyano groups; A terphenyl group unsubstituted or substituted with deuterium or cyano groups; A quaterphenyl group unsubstituted or substituted with deuterium or cyano groups; A naphthylphenyl group unsubstituted or substituted with deuterium or cyano groups; A naphthylbiphenyl group unsubstituted or substituted with deuterium or cyano groups; A phenyl naphthyl group unsubstituted or substituted with deuterium or cyano groups; Naphthyl naphthyl group unsubstituted or substituted with deuterium or cyano group; Or a biphenyl naphthyl group unsubstituted or substituted with deuterium or cyano groups.

According to the exemplary embodiment of the present specification, Ar1 is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with deuterium or cyano groups; A biphenyl group unsubstituted or substituted with deuterium; A terphenyl group unsubstituted or substituted with deuterium; A quaterphenyl group unsubstituted or substituted with deuterium; A naphthylphenyl group unsubstituted or substituted with deuterium; A naphthylbiphenyl group unsubstituted or substituted with deuterium; A phenylnaphthyl group unsubstituted or substituted with deuterium; A naphthyl naphthyl group unsubstituted or substituted with deuterium; Or a biphenyl naphthyl group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with deuterium or cyano groups; A biphenyl group unsubstituted or substituted with deuterium; A terphenyl group unsubstituted or substituted with deuterium; A quaterphenyl group unsubstituted or substituted with deuterium; A naphthylphenyl group unsubstituted or substituted with deuterium; A naphthylbiphenyl group unsubstituted or substituted with deuterium; A phenylnaphthyl group unsubstituted or substituted with deuterium; A naphthyl naphthyl group unsubstituted or substituted with deuterium; Or a biphenyl naphthyl group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group.

According to one embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, cyano groups, and aryl groups unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar1 is composed of 'deuterium, cyano group, a phenyl group unsubstituted or substituted with deuterium, a biphenyl group unsubstituted or substituted with deuterium, and a naphthyl group substituted or unsubstituted with deuterium'. It is a phenyl group unsubstituted or substituted with one or more substituents selected from the group.

According to an exemplary embodiment of the present specification, Ar1 is substituted with 'deuterium, cyano group, phenyl group unsubstituted or substituted with deuterium, biphenyl group unsubstituted or substituted with deuterium, or naphthyl group unsubstituted or substituted with deuterium'. Or an unsubstituted phenyl group.

In one embodiment of the present specification, Ar2 is an aryl group unsubstituted or substituted with R22.

In one embodiment of the present specification, R22 is deuterium; Cyano group; Alkyl groups; Alkenyl group; -ORh; -SiRiRjRk; -OSiRiRjRk; Or an aryl group, the Rh to Rk are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl groups; Or an aryl group.

According to an exemplary embodiment of the present specification, R22 is deuterium; Cyano group; Or an alkyl group.

According to an 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 quarterphenyl group; A substituted or unsubstituted naphthylphenyl group; A substituted or unsubstituted naphthylbiphenyl group; A substituted or unsubstituted phenylnaphthyl group; A substituted or unsubstituted naphthyl naphthyl group; Or a substituted or unsubstituted biphenyl naphthyl group.

According to an exemplary embodiment of the present specification, Ar2 is deuterium; A phenyl group unsubstituted or substituted with deuterium or cyano groups; A biphenyl group unsubstituted or substituted with deuterium or cyano groups; A terphenyl group unsubstituted or substituted with deuterium or cyano groups; A quaterphenyl group unsubstituted or substituted with deuterium or cyano groups; A naphthylphenyl group unsubstituted or substituted with deuterium or cyano groups; A naphthylbiphenyl group unsubstituted or substituted with deuterium or cyano groups; A phenyl naphthyl group unsubstituted or substituted with deuterium or cyano groups; Naphthyl naphthyl group unsubstituted or substituted with deuterium or cyano group; Or a biphenyl naphthyl group unsubstituted or substituted with deuterium or cyano groups.

According to an exemplary embodiment of the present specification, Ar2 is deuterium; A phenyl group unsubstituted or substituted with deuterium or cyano groups; A biphenyl group unsubstituted or substituted with deuterium; A terphenyl group unsubstituted or substituted with deuterium; A quaterphenyl group unsubstituted or substituted with deuterium; A naphthylphenyl group unsubstituted or substituted with deuterium; A naphthylbiphenyl group unsubstituted or substituted with deuterium; A phenylnaphthyl group unsubstituted or substituted with deuterium; A naphthyl naphthyl group unsubstituted or substituted with deuterium; Or a biphenyl naphthyl group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group.

According to an exemplary embodiment of the present specification, Ar2 is a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, cyano groups, and aryl groups unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar2 is made of 'deuterium, cyano group, a phenyl group unsubstituted or substituted with deuterium, a biphenyl group unsubstituted or substituted with deuterium, and a naphthyl group substituted or unsubstituted with deuterium'. It is a phenyl group unsubstituted or substituted with one or more substituents selected from the group.

According to an exemplary embodiment of the present specification, Ar2 is substituted with 'deuterium, cyano group, phenyl group unsubstituted or substituted with deuterium, biphenyl group unsubstituted or substituted with deuterium, or naphthyl group unsubstituted or substituted with deuterium'. Or an unsubstituted phenyl group.

According to an exemplary embodiment of the present specification, the group that does not bind to any one of Ar1 and R11 to R18 among the R1 to R8 deuterium; Or an alkyl group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, the group that does not bind to any one of Ar1 and R1 to R8 among R11 to R18 is deuterium; Or an alkyl group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, at least one of the groups that do not bind to any one of Ar1 and R11 to R18 among the R1 to R8; At least two; At least three; At least four; Or at least five are deuterium.

According to an exemplary embodiment of the present specification, at least one of the groups that do not bind to any one of Ar2 and R1 to R8 among the R11 to R18; At least two; At least three; At least four; Or at least five are deuterium.

According to an exemplary embodiment of the present specification, all groups that do not bind to any one of Ar1 and R11 to R18 among R1 to R8 are deuterium.

According to an exemplary embodiment of the present specification, all groups that do not bind to any one of Ar2 and R1 to R8 among R11 to R18 are deuterium.

According to an exemplary embodiment of the present specification, when Ar1 is a substituted or unsubstituted aryl group, Ar1 is at least 10%; At least 20%; At least 30%; At least 40%; At least 50%; At least 60%; At least 70%; At least 80%; At least 90% is deuterated.

According to an exemplary embodiment of the present specification, Ar2 is at least 10%; At least 20%; At least 30%; At least 40%; At least 50%; At least 60%; At least 70%; At least 80%; At least 90% is deuterated.

According to an exemplary embodiment of the present specification, the formula 1 is represented by any one of the following formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Chemical Formulas 1-1 to 1-3,

The definitions of R1 to R8, R11 to R18, Ar1 and Ar2 are the same as defined in Formula 1,

n1 to n3 are the same as or different from each other, and each independently an integer of 1 to 3.

According to an exemplary embodiment of the present specification, the formula 1 is represented by the formula 1-1 or 1-3.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is substituted with one or more deuterium. Such deuterated compounds can be prepared by known deuteration reactions. According to the exemplary embodiment of the present specification, the compound represented by Chemical 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.

In this specification, the degree of deuteration can be confirmed by a known method such as nuclear magnetic resonance spectroscopy ( ¹ H NMR) or GC / MS.

According to an exemplary embodiment of the present specification, Ar2 is represented by the following formula (a-1).

[Formula a-1]

In Chemical Formula a-1, d is an integer of 1 to 3,

는 R11 내지 R18 중 어느 하나에 연결되는 기이며,

Is a group connected to any one of R11 to R18,

R23 is hydrogen; heavy hydrogen; Cyano group; Alkyl groups; Alkenyl group; -ORh; -SiRiRjRk; -OSiRiRjRk; Or an aryl group, the Rh to Rk are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl groups; Or an aryl group.

According to an exemplary embodiment of the present specification, the n is 1.

According to an exemplary embodiment of the present specification, the n1 is 1.

According to an exemplary embodiment of the present specification, the n2 is 1.

According to an exemplary embodiment of the present specification, the n3 is 1.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is any one selected from the following compounds.

Hereinafter, an exemplary embodiment of the compound represented by Chemical Formula 2 will be described.

According to an exemplary embodiment of the present specification, the HAr is a substituted or unsubstituted nitrogen-containing heterocyclic group.

According to an exemplary embodiment of the present specification, the HAr is a substituted or unsubstituted C2-C42 nitrogen-containing heterocyclic group.

According to an exemplary embodiment of the present specification, the HAr is a substituted or unsubstituted C2-C38 nitrogen-containing heterocyclic group.

According to an exemplary embodiment of the present specification, the HAr is a substituted or unsubstituted C2-C34 nitrogen-containing heterocyclic group.

According to an exemplary embodiment of the present specification, the HAr is a substituted or unsubstituted C2-C30 nitrogen-containing heterocyclic group.

According to an exemplary embodiment of the present specification, the HAr is a substituted or unsubstituted heterocyclic group containing two or more N.

According to an exemplary embodiment of the present specification, the HAr is a substituted or unsubstituted 1 to 8 ring nitrogen-containing heterocyclic group.

According to an exemplary embodiment of the present specification, the HAr is a nitrogen-containing heterocyclic group unsubstituted or substituted with R51.

According to an exemplary embodiment of the present specification, the R51 is hydrogen; heavy hydrogen; Cyano group; An aryl group unsubstituted or substituted with deuterium, cyano or aryl groups; Or a heteroaryl group.

According to an exemplary embodiment of the present specification, the HAr is a pyrrolyl group, imidazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, triazinyl group, triazolyl group, acridinyl group, spirofluorene indolo Acridinyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, benzimidazoquinazolinyl group; Quinoxalinyl group, phthalazinyl group, pyridopyrimidyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolinyl group, indolyl group, carbazolyl group, imidazolyl group, benzimidazolyl group, benzo Thiazolyl group, benzocarbazolyl group, phenanthroline group, phenimidazophenantridinyl group; Aziridinyl group, azaindoleyl group, isoindoleyl group, indazolyl group, purinyl group, pteridinyl group, beta-carbonyl group, naphthyridinyl group, ter-pyridyl group, A phenazinyl group, an imidazopyridinyl group, a pyropyridinyl group, an azepinyl group or a pyrazolyl group, and may be substituted with R51.

According to an exemplary embodiment of the present specification, the HAr is a substituted or unsubstituted pyrimidinyl group; A substituted or unsubstituted pyridinyl group; A substituted or unsubstituted triazinyl group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted imidazolyl group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted phenanthrolinyl group; A substituted or unsubstituted benzo [4,5] imidazo [1,2-c] quinazolinyl group; A substituted or unsubstituted benzo [4,5] imidazo [1,2-f] phenantridinyl group; Or a substituted or unsubstituted spiro [fluorene-9,8'-indolo [3,2,1-di] acridinyl] group.

According to an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted divalent to tetravalent aryl group; Or a substituted or unsubstituted divalent to tetravalent heteroaryl group.

According to an exemplary embodiment of the present specification, L is a direct bond; -O-; A substituted or unsubstituted C6-C36 divalent to tetravalent aryl group; Or a substituted or unsubstituted C2-C36 divalent to tetravalent heteroaryl group.

According to an exemplary embodiment of the present specification, L is a direct bond; -O-; A substituted or unsubstituted C6-C30 divalent to tetravalent aryl group; Or a substituted or unsubstituted C2-C30 divalent to tetravalent heteroaryl group.

According to an exemplary embodiment of the present specification, L is a direct bond; -O-; A substituted or unsubstituted C6-C25 divalent to tetravalent aryl group; Or a substituted or unsubstituted C2-C25 divalent to tetravalent heteroaryl group.

According to an exemplary embodiment of the present specification, L is a direct bond; -O-; A divalent to tetravalent aryl group unsubstituted or substituted with R52; Or a divalent to tetravalent heteroaryl group unsubstituted or substituted with R53.

According to one embodiment of the present specification, R52 and R53 are the same as or different from each other, and each independently deuterium; Cyano group; Alkyl groups; An aryl group unsubstituted or substituted with a cyano group or an aryl group; Or a heteroaryl group.

According to an exemplary embodiment of the present specification, R52 is hydrogen.

According to an exemplary embodiment of the present specification, R53 is hydrogen.

According to an exemplary embodiment of the present specification, L is a direct bond; -O-; A substituted or unsubstituted divalent to tetravalent phenyl group; A substituted or unsubstituted divalent to tetravalent biphenyl group; A substituted or unsubstituted divalent to tetravalent naphthyl group; A substituted or unsubstituted divalent to tetravalent fluorenyl group; A substituted or unsubstituted divalent to tetravalent anthracenyl group; A substituted or unsubstituted divalent to tetravalent spiro [fluorene-9,9'-xanthene] group; A substituted or unsubstituted divalent to tetravalent pyridinyl group; A substituted or unsubstituted divalent to tetravalent carbazolyl group; A substituted or unsubstituted divalent to tetravalent benzimidazole group; Or a substituted or unsubstituted divalent to tetravalent dibenzofuranyl group.

In some embodiments of L, the substituent at “substituted or unsubstituted” is deuterium; Cyano group; An aryl group unsubstituted or substituted with deuterium, an alkyl group, a cyano group, or a heteroaryl group; Or it may be a heteroaryl group unsubstituted or substituted with deuterium, cyano or aryl groups.

According to one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6-C36 arylene group; Or a substituted or unsubstituted C2-C36 heteroarylene group.

According to one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6-C30 arylene group; Or a substituted or unsubstituted C2-C30 heteroarylene group.

According to one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6-C25 arylene group; Or a substituted or unsubstituted C2-C5 heteroarylene group.

According to one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted divalent spiro [fluorene-9,9'-xanthene] group; A substituted or unsubstituted divalent pyridinyl group; A substituted or unsubstituted divalent carbazolyl group; A substituted or unsubstituted divalent benzimidazole group; Or a substituted or unsubstituted divalent dibenzofuranyl group.

According to one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Deuterium, alkyl group, cyano group, aryl group, aryl group substituted with cyano group, aryl group substituted with alkyl group, aryl group substituted with aryl group, aryl group substituted with heteroaryl group, or C6 substituted or unsubstituted with heteroaryl group -C25 arylene group; Or deuterium, alkyl group, cyano group, aryl group, aryl group substituted with cyano group, aryl group substituted with alkyl group, aryl group substituted with aryl group, aryl group substituted with heteroaryl group, or substituted or unsubstituted with heteroaryl group It is a substituted or unsubstituted C2-C5 heteroarylene group.

In some embodiments of L1 and L2, the substituent at "substituted or unsubstituted" is deuterium; Cyano group; An aryl group unsubstituted or substituted with deuterium, an alkyl group, a cyano group, or a heteroaryl group; Or it may be a heteroaryl group unsubstituted or substituted with deuterium, cyano or aryl groups.

According to an exemplary embodiment of the present specification, the L,-(L1) _a1 - _and- (L2) _b1 -are not all direct bonds.

According to an exemplary embodiment of the present specification, at least two of the L,-(L1) _a1 - _and- (L2) _b1 -is not a direct bond.

According to an exemplary embodiment of the present specification, at least one of the L,-(L1) _a1 - _and- (L2) _b1 -is a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present specification, the L, L1 and L2 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.

According to one embodiment of the present specification, L is a substituted or unsubstituted divalent to tetravalent heteroaryl group, or at least one of L1 and L2 is a substituted or unsubstituted heteroarylene group.

According to an exemplary embodiment of the present specification, R61 and R62 are the same as or different from each other, and each independently deuterium; Cyano group; Alkyl groups; Aryl group; Or a heteroaryl group.

According to an exemplary embodiment of the present specification, R61 and R62 are the same as or different from each other, and each independently deuterium; Cyano group; Methyl group; Phenyl group; Dibenzofuranyl group; Or a pyridinyl group.

According to an exemplary embodiment of the present specification, a is 1.

According to an exemplary embodiment of the present specification, a is 2.

According to an exemplary embodiment of the present specification, b is 1.

According to an exemplary embodiment of the present specification, b is 2.

According to an exemplary embodiment of the present specification, a1 and b1 are each 0.

According to an exemplary embodiment of the present specification, the sum of a1 and b1 is 1 or more.

According to an exemplary embodiment of the present specification, the sum of a1 and b1 is 2.

According to an exemplary embodiment of the present specification, the sum of a1 and b1 is 3.

According to an exemplary embodiment of the present specification, the sum of a1 and b1 is 4.

According to an exemplary embodiment of the present specification, a2 is 1.

According to an exemplary embodiment of the present specification, b2 is 1.

According to the exemplary embodiment of the present specification, L is a substituted or unsubstituted monovalent to tetravalent heteroaryl group, or at least one of L1 and L2 is a substituted or unsubstituted heteroarylene group.

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

This specification is an anode; cathode; A light emitting layer provided between the anode and the cathode; And an organic material layer provided between the cathode and the light emitting layer, wherein the light emitting layer includes a compound represented by Formula 1, and the organic material layer provided between the cathode and the light emitting layer is represented by Formula 2 It provides an organic light-emitting device comprising a compound.

In the present specification, the meaning that a specific A material is included in the B layer is: ① one or more A materials are included in one B layer, and ② the B layer is composed of one or more layers, and the A material is among the multi-layer B layers. It includes all included in the first floor or higher.

In the present specification, the meaning that a specific A material is included in the C layer or the D layer is ① included in one or more of the C layers of one or more layers, ② included in one or more of the D layers of one or more layers, or ③ one layer It includes everything contained in the above-mentioned C layer and one or more layers of D layer.

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, the organic material layer between the anode and the light emitting layer may be a hole injection layer, a hole transport layer, a layer simultaneously performing hole transport and injection, or a hole control layer. The organic material layer between the cathode and the light emitting layer may be an electron control layer, an electron transport layer, an electron injection layer, or a layer that simultaneously transports and injects electrons. The organic light emitting device may include one or more layers having the same function.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is included in the light emitting layer. The organic light-emitting device may further include other light-emitting layers. In one embodiment, when two or more light-emitting layers are included, each light-emitting layer may include the same or different materials, and the color of light-emitting may also be the same or different.

In one embodiment of the present specification, the organic light emitting device includes one light emitting layer.

In one embodiment of the present specification, the content of the compound represented by Chemical Formula 1 is 50 parts by weight or more and 100 parts by weight or less compared to 100 parts by weight of the total weight of the light emitting layer.

In one embodiment of the present specification, the light emitting layer including the compound represented by Chemical Formula 1 further includes a dopant. The dopant may include 1 part by weight or more and less than 50 parts by weight based on 100 parts by weight of the total weight of the light emitting layer.

In one embodiment of the present specification, the compound represented by Chemical Formula 2 is included in the organic material layer between the cathode and the light emitting layer.

In one embodiment of the present specification, the compound represented by Chemical Formula 2 is included in 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 organic material layer including the compound represented by Chemical Formula 2 includes an electron injection layer; Electron transport layer; Electron injection and transport layer; Or an electron control layer.

In one embodiment of the present specification, the organic material layer including the compound represented by Chemical Formula 2 is an electron injection and transport layer.

In one embodiment of the present specification, the organic material layer including the compound represented by Chemical Formula 2 is provided in contact with the light emitting layer.

In one embodiment of the present specification, the organic material layer including the compound represented by Chemical Formula 2 is provided in contact with the light emitting layer containing the compound represented by Chemical Formula 1.

In the present specification, the 'layer' is a meaning that is 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 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.

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

The organic light emitting device according to an exemplary embodiment of the present invention may include a substrate 1, an anode 2, a light emitting layer 8, an organic material layer 3, and a cathode 4, as shown in FIG. 1. In one embodiment, the compound represented by Chemical Formula 1 is included in the light-emitting layer 8, and the compound represented by Chemical Formula 2 is included in the organic material layer 3.

The organic light emitting device according to an exemplary embodiment of the present invention includes a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 7, a light emitting layer as shown in FIG. (8), an electron control layer (9), an electron transport layer (10), an electron injection layer (11), and a cathode (4). In one embodiment, the compound represented by Chemical Formula 1 is included in the light emitting layer 8. In one embodiment, the compound represented by Chemical Formula 2 is included in the electron control layer 9, the electron transport layer 10, or the electron injection layer 11.

The organic light emitting device according to an exemplary embodiment of the present invention includes a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6a, and a second hole transport layer 6b as shown in FIG. ), A light emitting layer 8, an electron injection and transport layer 12 and a cathode (4). In one embodiment, the compound represented by Chemical Formula 1 is included in the light emitting layer 8. In one embodiment, the compound represented by Formula 2 is included in the electron injection and transport layer 12.

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 3, 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 / electron control layer / electron transport layer / electron injection layer / cathode

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 then forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, 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 formed 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, for example 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 compound represented by Chemical Formula 1 is formed as a light emitting layer by a solution coating method in the manufacture of an organic light emitting device.

In one embodiment of the present specification, the compound represented by Chemical Formula 2 is formed of an organic material layer provided between the cathode and the light emitting layer by vapor deposition. In this case, a physical vapor deposition method (PVD, physical vapor deposition) such as sputtering or e-beam evaporation may be used, but the present invention is not limited thereto.

In one embodiment of the present specification, other layers in the organic light-emitting device may 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. Specific examples of the positive electrode 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 metal and oxide such as ZnO: Al or SnO ₂ : 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. Specific examples of the negative electrode material include 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 hole injection layer is a layer for injecting holes received from an electrode into an emission layer or an adjacent layer provided toward the emission layer. The hole injection material has the ability to transport holes and has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and moves excitons generated in the light emitting layer to the electron injection layer or the electron injection material. It is preferable to use a compound that prevents and also has excellent thin film forming ability. It is preferable that the highest 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 porphyrin, oligothiophene, arylamine-based organic matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, perylene There are organic-based organic materials, anthraquinones, 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 the holes to the light emitting layer. As the hole transport material, a material capable of receiving holes from an anode or a hole injection layer and transporting holes to a light emitting layer is suitable as a material having high mobility for holes. Specific examples of the hole transport material include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

The hole control layer is a layer that prevents electrons from entering the anode to the light emitting layer and controls the performance of the entire device by controlling the flow of holes flowing into the light emitting layer. The hole control material is preferably a compound having the ability to prevent the inflow of electrons from the light emitting layer to the anode, and to control the flow of holes injected into the light emitting layer or light emitting material. In one embodiment, as the hole control layer, an arylamine-based organic material may be used, but is not limited thereto.

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

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, and the like, and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladders. Type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material for the light emitting layer include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. As the aromatic amine derivative, as a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, pyrene, anthracene, chrysene, periplanene and the like having an arylamine group can be used. As the styrylamine compound, a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine may be used. Examples of the styrylamine compound include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. The metal complex may be an iridium complex, a platinum complex, or the like, but is not limited thereto.

The electron control layer is a layer that blocks holes from entering the cathode from the light emitting layer and controls electrons flowing into the light emitting layer to control the performance of the entire device. As the electron regulating material, a compound having the ability to prevent the inflow of holes from the light emitting layer to the cathode and to control the electrons injected into the light emitting layer or the light emitting material is preferable. As the electron regulating material, an appropriate material may be used depending on the composition of the organic material layer used in the device. The electron control layer is positioned between the light emitting layer and the cathode, and is preferably provided in direct contact with the light emitting layer.

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 from the cathode well and transferring them to the light emitting layer, a material having high mobility for electrons is suitable. Examples of the electron transport material include an Al complex of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited to these. The electron transport layer can be used with any desired negative electrode material as used according to the prior art. In one embodiment, the negative electrode material includes a material having a low work function; And an aluminum layer or a silver layer. Examples of the material having a low work function include cesium, barium, calcium, ytterbium, and samarium. After forming a layer with the material, an aluminum layer or a silver layer may be formed on the layer.

The electron injection layer is a layer that injects electrons received from the electrode into the light emitting layer. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, In addition, it is preferable to use a compound having excellent thin film forming ability. 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, 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) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

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 specification is not interpreted to be limited to the embodiments described below. The embodiments of the present specification are provided to more fully describe the present specification to those skilled in the art.

Manufacturing example

<Synthesis of Compound 1-1>

1-bromo-2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalene (20g, 47.2mmol) and 4,4,5,5-tetramethyl-2- (2-methyl-4- ( 4- (naphthalen-1-yl) phenyl) naphthalen-1-yl) -1,3,2-dioxaborolane (24.4 g, 52 mmol) was added to 250 mL of Tetrahydrofuran solvent and stirred. Add potassium carbonate (13.1 g 94.5 mmol) aqueous solution and raise the temperature. When distillation starts, add Tetrakis (triphenylphosphine) palladium (0) (1.64g, 1.42mmol) and stir for an additional 4 hours. After completion of the reaction, compound 1-1-A was prepared through filtration and ethanol purification (28 g, yield 86.2%). Compound 1-1-A was dissolved in Benzene-d6 in an inert environment and stirred for 2 hours with trichlorobenzene. The reaction was terminated through D ₂ O quenching to obtain compound 1-1.

[M + H] ⁺ = 719

<Synthesis of Compound 1-2>

1-bromo-4- (4- (naphthalen-1-yl) phenyl) naphthalene is used instead of 1-bromo-2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalene, and 4, 4,5,5-tetramethyl-2- (2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalen-1-yl) -1,3,2-dioxaborolane instead of 4,4,5, Same as the synthesis method of Compound 1-1, except that 5-tetramethyl-2- (4- (3- (naphthalen-1-yl) phenyl) naphthalen-1-yl) -1,3,2-dioxaborolane was used. Compound 1-2 was prepared by the method.

[M + H] ⁺ = 693

<Synthesis of Compound 1-3>

Instead of 1-bromo-2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalene, 1-bromo-4- (4- (naphthalen-1-yl) phenyl) naphthalene is used, and 4, 4,5,5-tetramethyl-2- (2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalen-1-yl) -1,3,2-dioxaborolane instead of 5- (4- ( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-1-yl) isophthalonitrile, except that compound 1-3 was synthesized in the same manner as in compound 1-1. Was prepared.

[M + H] ⁺ = 606

<Synthesis of Compound 1-4>

Instead of 1-bromo-2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalene, 1-bromo-4- (4- (naphthalen-2-yl) phenyl) naphthalene is used, and 4 , 4,5,5-tetramethyl-2- (2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalen-1-yl) -1,3,2-dioxaborolane instead of (4- (4 Compound 1-4 was prepared by the same method as the synthesis method of compound 1-1, except that-(naphthalen-1-yl) phenyl) naphthalen-1-yl) boronic acid was used.

[M + H] ⁺ = 693

<Synthesis of Compound 1-5>

1-([1,1 ': 3', 1 "-terphenyl] -3-yl) -4- instead of 1-bromo-2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalene bromonaphthalene is used, and the 4,4,5,5-tetramethyl-2- (2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalen-1-yl) -1,3,2- 2- (4-([1,1 ': 3', 1 "-terphenyl] -3-yl) naphthalen-1-yl) -4,4,5,5-tetramethyl-1,3,2- instead of dioxaborolane Compound 1-5 was manufactured by the same method as the synthesis method of compound 1-1, except that dioxaborolane was used.

[M + H] ⁺ = 749

<Synthesis of Compound 1-6>

1-bromo-4- (4- (naphthalen-1-yl) phenyl) naphthalene is used instead of the 1-bromo-2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalene, and the 4 4,4,5 instead of, 4,5,5-tetramethyl-2- (2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalen-1-yl) -1,3,2-dioxaborolane Synthesis of the compound 1-1, except for the use of, 5-tetramethyl-2- (6- (4- (naphthalen-1-yl) phenyl) naphthalen-2-yl) -1,3,2-dioxaborolane Compound 1-6 was obtained by the same method.

[M + H] ⁺ = 693

<Synthesis of Compound 1-7>

Instead of 1-bromo-2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalene, 1-bromo-4- (3- (naphthalen-1-yl) phenyl) naphthalene is used, and the 4 4,4,5 instead of, 4,5,5-tetramethyl-2- (2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalen-1-yl) -1,3,2-dioxaborolane Synthesis of the compound 1-1, except that, 5-tetramethyl-2- (4- (3- (naphthalen-1-yl) phenyl) naphthalen-1-yl) -1,3,2-dioxaborolane was used. Compound 1-7 was obtained by the same method.

[M + H] ⁺ = 693

<Synthesis of Compound 1-8>

1-bromo-4- (4- (naphthalen-1-yl) phenyl) naphthalene is used instead of the 1-bromo-2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalene, and the 4 Instead of, 4,5,5-tetramethyl-2- (2-methyl-4- (4- (naphthalen-1-yl) phenyl) naphthalen-1-yl) -1,3,2-dioxaborolane 4- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-1-yl) benzonitrile except for using compound 1-1 in the same manner as in compound 1-1 8 was prepared.

[M + H] ⁺ = 585

<Synthesis of Compound 2-1>

2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine (30g, 58.3mmol) and 2- (4'-cyano- [1,1 ' -biphenyl] -4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (19.6g, 64.1mmol) was dissolved in 300 mL of Tetrahydrofuran and stirred. Add an aqueous solution of potassium carbonate (16.1g, 116.6mmol) and increase the temperature. When reflux begins, add Tetrakis (triphenylphosphine) palladium (0) (2.02g, 1.75mmol) catalyst and stir for 3 hours. After completion of the reaction, Compound 2-1 (31 g, yield 87%) was prepared through cooling and ethanol slurry purification.

[M + H] ⁺ = 613

<Synthesis of Compound 2-2>

2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine And 5 '-(4- (4- instead of 2- (4'-cyano- [1,1'-biphenyl] -4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenoxy) phenyl)-[1,1 ': 3', 1 "-terphenyl] -2,2" -dicarbonitrile Compound 2-2 was manufactured according to the same method as the synthesis method of Compound 2-1, except for the use.

[M + H] ⁺ = 680

<Synthesis of Compound 2-3>

2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- (4-chlorophenyl) -4-phenyl-6- (1- (triphenylen -2-yl) naphthalen-2-yl) -1,3,5-triazine is used, and 2- (4'-cyano- [1,1'-biphenyl] -4-yl) -4,4,5 Compound 2-3 was prepared by the same method as the synthesis method of Compound 2-1, except that (3-cyanophenyl) boronic acid was used instead of, 5-tetramethyl-1,3,2-dioxaborolane.

[M + H] ⁺ = 687

<Synthesis of Compound 2-4>

2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- (4-bromophenyl) -4,6-diphenyl-1,3,5 -triazine, 3- (9 instead of 2- (4'-cyano- [1,1'-biphenyl] -4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane , 9-diphenyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-fluoren-2-yl) benzonitrile, except that compound 2-1 Compound 2-4 was prepared by the same method as the synthesis method.

[M + H] ⁺ = 727

<Synthesis of Compound 2-5>

2- (3- (9,9-diphenyl-9H-fluoren-2-yl instead of 2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine ) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine, 2- ( Compound 2-1, except that 4-bromobenzonitrile was used instead of 4'-cyano- [1,1'-biphenyl] -4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane Compound 2-5 was prepared by the same method as the synthesis method.

[M + H] ⁺ = 727

<Synthesis of Compound 2-6>

Instead of 2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine, 7- (3- (4,6-diphenyl-1,3,5-triazin -2-yl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9,9-dimethyl-9H-fluorene-2-carbonitrile 2- (4'-cyano- [1,1'-biphenyl] -4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of 2- (4-bromophenyl) pyridine Compound 2-6 was manufactured by the same method as the synthesis method of Compound 2-1, except for the above.

[M + H] ⁺ = 680

<Synthesis of Compound 2-7>

4-([1,1'-biphenyl] -4-yl) -6- instead of 2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine (4- (4-bromonaphthalen-1-yl) phenyl) -2-phenylpyrimidine and 2- (4'-cyano- [1,1'-biphenyl] -4-yl) -4,4,5,5 Compound in the same manner as in the synthesis method of Compound 2-1, except that (3'-cyano- [1,1'-biphenyl] -4-yl) boronic acid was used instead of tetramethyl-1,3,2-dioxaborolane 2-7 was prepared.

[M + H] ⁺ = 688

<Synthesis of Compound 2-8>

4- (9-phenyl-1,10-phenanthrolin-2-yl) naphthalen- instead of 2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine 1-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate, 2- (4'-cyano- [1,1'-biphenyl] -4-yl ) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of 9,9-dimethyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl ) -9H-fluorene-2-carbonitrile, except that the compound 2-8 was prepared in the same manner as in the synthesis method of compound 2-1.

[M + H] ⁺ = 600

<Synthesis of Compound 2-9>

2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2-bromo-9,10-bis (phenyl-d5) anthracene and 2 -(4'-cyano- [1,1'-biphenyl] -4-yl) -4 (4,5-diphenyl-2- instead of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Synthesis of Compound 2-1, except that (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1H-imidazol-1-yl) benzonitrile was used Compound 2-9 was prepared by the same method as the method.

[M + H] ⁺ = 736

<Synthesis of Compound 2-10>

Instead of 2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine, 9-bromo-10- (naphthalen-2-yl) anthracene is used and 2- (4'-cyano- [1,1'-biphenyl] -4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of 4- (3- (4,4,5, Synthesis of Compound 2-1, except that 5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [4,5] imidazo [1,2-c] quinazolin-6-yl) benzonitrile was used Compound 2-10 was prepared by the same method as.

[M + H] ⁺ = 623

<Synthesis of Compound 2-11>

2,7-dibromospiro [fluorene-9,8'-indolo [3,2, instead of 2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine 1-de] acridine] and instead of 2- (4'-cyano- [1,1'-biphenyl] -4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( Compound 2-11 was prepared by the same method as the synthesis method of compound 2-1, except that 4-cyanophenyl) boronic acid was used.

[M + H] ⁺ = 608

<Synthesis of Compound 2-12>

2- (10-bromoanthracen-9-yl) benzonitrile was used instead of 2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine and 2- (4 spiro [fluorene-9,8'-indolo [3,2] instead of '-cyano- [1,1'-biphenyl] -4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane Compound 1-12 was prepared by the same method as the synthesis method of Compound 2-1, except that, 1-de] acridin] -2-ylboronic acid was used.

[M + H] ⁺ = 683

<Synthesis of Compound 2-13>

2- (4- (4-bromodibenzo [b, d] furan-3-yl instead of 2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine ) phenyl) -4,6-diphenyl-1,3,5-triazine and 2- (4'-cyano- [1,1'-biphenyl] -4-yl) -4,4,5,5- Instead of tetramethyl-1,3,2-dioxaborolane, 9,9-dimethyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-fluorene-2-carbonitrile Compound 2-13 was manufactured by the same method as the synthesis method of compound 2-1, except that it was used.

[M + H] ⁺ = 693

<Synthesis of Compound 2-14>

2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2,4-diphenyl-6- (3 '-(4,4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl) -1,3,5-triazine and 2- (4'-cyano- [ 2-chlorospiro [fluorene-9,9'-xanthene] -7-carbonitrile was used instead of 1,1'-biphenyl] -4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane Compound 2-14 was manufactured by the same method as the synthesis method of Compound 2-1, except for the above.

[M + H] ⁺ = 741

<Synthesis of Compound 2-15>

2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 6,6 '-(5-chloro-1,3-phenylene) bis (2 , 4-diphenyl-1,3,5-triazine) and 2- (4'-cyano- [1,1'-biphenyl] -4-yl) -4,4,5,5-tetramethyl-1, 9,9-dimethyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-fluorene-2-carbonitrile instead of 3,2-dioxaborolane , Compound 2-15 was prepared by the same method as the synthesis method of compound 2-1.

[M + H] ⁺ = 758

<Synthesis of Compound 2-16>

2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 9,9 '-(5-chloro-1,3-phenylene) bis (9H -carbazole) and 9,9- instead of 2- (4'-cyano- [1,1'-biphenyl] -4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane Same as the synthesis method of compound 2-1, except that dimethyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-fluorene-2-carbonitrile was used. Compound 2-16 was prepared by the method.

[M + H] ⁺ = 626

<Synthesis of Compound 2-17>

3 ', 5'-dibromo- [1,1'-biphenyl] -4- instead of 2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine 4-phenyl-2- instead of 2- (4'-cyano- [1,1'-biphenyl] -4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane using carbonitrile (6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridin-2-yl) quinoline was used in the same manner as in the synthesis method of Compound 2-1. Compound 2-17 was prepared.

[M + H] ⁺ = 740

<Synthesis of Compound 2-18>

Instead of 2- (4- (4-bromonaphthalen-1-yl) phenyl) -4,6-diphenyl-1,3,5-triazine, 1,6-dibromopyrene is used and 2- (4'-cyano- [1, Instead of 1'-biphenyl] -4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane 4- (2- (4- (4,4,5,5-tetramethyl-1, Compound 2-18 was prepared by the same method as the synthesis method of compound 2-1, except that 3,2-dioxaborolan-2-yl) phenyl) -1H-benzo [d] imidazol-1-yl) benzonitrile was used. .

[M + H] ⁺ = 789

<Example 1>

A glass substrate coated with a thin film of indium tin oxide (ITO) at a thickness of 100 nm was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as the detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as the 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 transporting 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 vapor-deposited to a thickness of 60 nm on the prepared ITO transparent electrode to form a hole injection layer.

The following compound HAT was vacuum deposited on the hole injection layer to form a first hole transport layer having a thickness of 5 nm, and the following compound HT-A was vacuum deposited on the first hole transport layer to form a second hole transport layer having a thickness of 50 nm. .

Subsequently, on the second hole transport layer, Compound 1-1 and Compound BD were vacuum-deposited in a weight ratio of 25: 1 to form a light emitting layer having a thickness of 20 nm.

The compound 2-1 and the following compound LiQ were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 35 nm.

After depositing lithium fluoride (LiF) to a thickness of 1 nm on the electron injection and transport layer, aluminum was then deposited to a thickness of 100 nm to form a cathode to prepare an organic light emitting device.

In the above process, the deposition rate of the organic material was maintained at 0.04 nm / sec to 0.09 nm / sec, the deposition rate of lithium fluoride was maintained at 0.03 nm / sec, and the deposition rate of aluminum was maintained at 0.2 nm / sec. The vacuum degree during deposition was maintained between 1Х10 ^-7 torr and 5Х10 ^-5 torr.

<Examples 2 to 18>

An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound of Table 1 below instead of the compound 1-1 and the compound 2-1 of Example 1.

<Comparative Examples 1 to 6>

An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound of Table 1 below instead of the compound 1-1 and the compound 2-1 of Example 1. In particular, the electron injection and transport layers of the devices of Comparative Examples 3 and 4 were formed using only the compound LiQ.

The voltages and efficiencies of the organic light-emitting devices of Examples and Comparative Examples were measured under a current density of 10 mA / cm ² , and the lifespan (LT ₉₀ ) was measured under a current density of 20 mA / cm ² , and the results are shown in Table 1 below. Did. At this time, LT ₉₀ means a time when the luminance becomes 90% compared to the initial luminance. The color coordinate (x, y) means the CIE color coordinate.

Emitting layer Electron injection and transport layer Voltage
(V) efficiency
(cd / A) Color coordinate
(x, y) LT ₉₀ (h) Example 1 Compound 1-1 Compound 2-1 4.04 4.97 (0.142, 0.097) 302 Example 2 Compound 1-1 Compound 2-2 4.01 4.85 (0.142, 0.097) 261 Example 3 Compound 1-2 Compound 2-3 4.06 4.94 (0.142, 0.098) 287 Example 4 Compound 1-2 Compound 2-4 4.09 5.01 (0.142, 0.096) 277 Example 5 Compound 1-4 Compound 2-5 4.03 4.88 (0.142, 0.097) 271 Example 6 Compound 1-5 Compound 2-6 3.99 4.97 (0.142, 0.097) 278 Example 7 Compound 1-3 Compound 2-7 4.08 5.01 (0.142, 0.097) 280 Example 8 Compound 1-6 Compound 2-8 4.04 4.99 (0.142, 0.096) 283 Example 9 Compound 1-3 Compound 2-9 4.06 4.95 (0.142, 0.097) 257 Example 10 Compound 1-7 Compound 2-10 4.12 5.6 (0.142, 0.097) 274 Example 11 Compound 1-1 Compound 2-11 3.96 5.13 (0.142, 0.096) 287 Example 12 Compound 1-8 Compound 2-12 3.97 5.08 (0.142, 0.096) 269 Example 13 Compound 1-1 Compound 2-13 4.01 5.00 (0.142, 0.096) 282 Example 14 Compound 1-2 Compound 2-14 4.04 5.04 (0.142, 0.097) 274 Example 15 Compound 1-2 Compound 2-15 4.03 4.95 (0.142, 0.096) 287 Example 16 Compound 1-5 Compound 2-16 4.06 4.88 (0.142, 0.097) 289 Example 17 Compound 1-7 Compound 2-17 4.03 4.96 (0.142, 0.096) 279 Example 18 Compound 1-8 Compound 2-18 4.10 5.03 (0.142, 0.097) 294 Comparative Example 1 Compound 1-1 Compound E1 4.20 4.50 (0.142, 0.097) 100 Comparative Example 2 Compound 1-2 Compound E2 4.37 4.45 (0.142, 0.097) 117 Comparative Example 3 Compound 1-1 - 4.17 4.64 (0.142, 0.096) 96 Comparative Example 4 Compound 1-3 - 4.22 4.36 (0.142, 0.097) 99 Comparative Example 5 Compound BH1 Compound 2-4 4.16 4.63 (0.142, 0.097) 103 Comparative Example 6 Compound BH2 Compound 2-7 4.26 4.55 (0.142, 0.097) 110

From Table 1, it was confirmed that the device comprising the compound represented by Formula 1 of the present invention in the light-emitting layer and the compound represented by Formula 2 in the organic material layer between the cathode and the light-emitting layer has characteristics of low voltage, high efficiency, and high life. .

In addition, a compound not containing a cyano group as in Comparative Examples 1 and 2 is included in the organic material layer between the negative electrode and the light emitting layer, or a compound represented by Formula 2 as in Comparative Examples 3 and 4 is not included between the negative electrode and the light emitting layer, When using a compound that does not contain deuterium as a host of the light emitting layer, such as Comparative Examples 5 and 6, when compared with the device using the compounds of the present invention, it is confirmed that the driving voltage is high, the light emission efficiency is low, and the lifetime characteristics are particularly low. Did.

1: Substrate
2: anode
3: organic layer
4: Cathode
5: hole injection layer
6: hole transport layer
6a: first hole transport layer
6b: second hole transport layer
7: hole control layer
8: emitting layer
9: Electronic control layer
10: electron transport layer
11: electron injection layer
12: electron injection and transport layer

Claims (13)

anode; cathode; A light emitting layer provided between the anode and the cathode; And an organic material layer provided between the cathode and the light emitting layer, wherein the light emitting layer includes a compound represented by Formula 1, and the organic material layer provided between the cathode and the light emitting layer is represented by Formula 2 below. Organic light emitting device comprising a compound:
[Formula 1]

In Chemical Formula 1,
Any one of R1 to R8 is a group connected to any one of Ar1 or R11 to R18, one is a group connected to any one of R11 to R18, and the rest are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; -OR; -SiRaRbRc; -OSiRaRbRc; Or a substituted or unsubstituted aryl group,
Any one of R11 to R18 is a group connected to any one of Ar2 or R1 to R8, one is a group connected to any one of R1 to R8, and the rest are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; -OR; -SiRaRbRc; -OSiRaRbRc; Or a substituted or unsubstituted aryl group,
R and Ra to Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl groups; Or an aryl group,
Ar1 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group,
Ar2 is a substituted or unsubstituted aryl group,
n is an integer from 1 to 3,
The compound represented by Formula 1 includes at least one deuterium,
[Formula 2]

In Chemical Formula 2,
HAr is a substituted or unsubstituted nitrogen-containing heterocyclic group,
L is a direct bond; -O-; A substituted or unsubstituted divalent to tetravalent aryl group; Or a substituted or unsubstituted divalent to tetravalent heteroaryl group,
L1 and L2 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,
a1 is an integer from 0 to 3, and when a1 is 2 or more, L1 is the same or different from each other, b1 is an integer from 0 to 3, and when b1 is 2 or more, L2 is the same or different from each other,
a is 1 or 2, b is 1 or 2, and when b is 2, HAr is the same or different from each other,
a2 is 1 or 2, b2 is 1 or 2,
When a2 is 2,-[(L1) _a1- (CN) _a ] is the same as or different from each other,
When b2 is 2,-[(L2) _b1- (HAr) _b ] is the same as 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 formula 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Chemical Formulas 1-1 to 1-3,
The definitions of R1 to R8, R11 to R18, Ar1 and Ar2 are the same as defined in Formula 1,
n1 to n3 are the same as or different from each other, and each independently an integer of 1 to 3. The method according to claim 1, wherein Ar1 is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted quarterphenyl group; A substituted or unsubstituted naphthylphenyl group; A substituted or unsubstituted naphthylbiphenyl group; A substituted or unsubstituted phenylnaphthyl group; A substituted or unsubstituted naphthyl naphthyl group; Or a substituted or unsubstituted biphenyl naphthyl group. The method according to claim 1, wherein Ar2 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted quarterphenyl group; A substituted or unsubstituted naphthylphenyl group; A substituted or unsubstituted naphthylbiphenyl group; A substituted or unsubstituted phenylnaphthyl group; A substituted or unsubstituted naphthyl naphthyl group; Or a substituted or unsubstituted biphenyl naphthyl group. The method according to claim 1, wherein the compound represented by the formula (1) is at least 10% deuterated organic light emitting device. The method according to claim 1, At least one of the Ar1 and Ar2 is an organic light emitting device that is an aryl group substituted with deuterium. The method according to claim 1, wherein the HAr is a substituted or unsubstituted pyrimidinyl group; A substituted or unsubstituted pyridinyl group; A substituted or unsubstituted triazinyl group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted imidazolyl group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted phenanthrolinyl group; A substituted or unsubstituted benzo [4,5] imidazo [1,2-c] quinazolinyl group; A substituted or unsubstituted benzo [4,5] imidazo [1,2-f] phenantridinyl group; Or a substituted or unsubstituted spiro [fluorene-9,8'-indolo [3,2,1-di] acridinyl] group. The method according to claim 1, wherein a is an organic light emitting device of 2. The organic light emitting diode of claim 1, wherein b is 2. The method according to claim 1, wherein L is a substituted or unsubstituted divalent to tetravalent heteroaryl group, or at least any one of L1 and L2 is a substituted or unsubstituted heteroarylene group organic light emitting device. 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 organic material layer containing the compound represented by the formula (2) is an electron injection layer; Electron transport layer; Electron injection and transport layer; Or an organic light-emitting device that is an electron control layer. The method according to claim 1, The content of the compound represented by the formula (1) is an organic light-emitting device that is 50 parts by weight or more and 100 parts by weight or less compared to 100 parts by weight of the total weight of the light emitting layer.

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