KR102230986B1 - Compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification provides a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

Description

Compound and organic light emitting device containing the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

The present invention relates to a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0041093 filed with the Korean Intellectual Property Office on April 9, 2018, the entire contents of which are incorporated herein.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic light-emitting device using the organic light-emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer has a multi-layered structure made of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls to the ground.

Development of a new material for the organic light emitting device as described above is continuously required.

Korean Patent Application Publication No. 10-2007-0091540

The present specification provides a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

R1 to R6 and Y1 to Y4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, and at least one of R1 to R6 is a cyano group.

An exemplary embodiment of the present specification is a cathode; anode; And an organic material layer provided between the cathode and the anode, wherein the compound represented by Formula 1 is included in the organic material layer.

Another exemplary embodiment of the present specification is a cathode; anode; At least two light emitting units provided between the cathode and the anode; And a charge generating layer provided between at least two of the two or more light emitting units, wherein the compound represented by Formula 1 is included in the charge generating layer. do.

The compound represented by Formula 1 may be used as a material for an organic material layer of an organic light-emitting device, and is preferably used for a hole transport layer, a hole injection layer, a hole control layer, a layer that simultaneously injects and transports holes, or a p-type charge generation layer. I can.

In one embodiment, the efficiency of the organic light-emitting device including the compound of the present invention is improved.

In one embodiment, the driving voltage of the organic light-emitting device including the compound of the present invention is lowered.

In an exemplary embodiment, the lifespan characteristics of the organic light emitting device including the compound of the present invention are improved.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.
2 shows 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 8, an electron transport layer 9, and an electron injection layer 10. And an example of an organic light-emitting device comprising the cathode 4 is shown.
3 shows a substrate 1, an anode 2, a first light-emitting unit 11, an N-type charge generation layer 12, a P-type charge generation layer 13, a second light-emitting unit 14, and a cathode 4 ) Shows an example of an organic light-emitting device.

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

The present specification provides a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

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

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 "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group; Silyl group; Nitro group; Carbonyl group; Ester group; Haloalkoxy group; Haloalkyl group; Phosphine oxide group; Alkyl sulfoxy group; Arylsulfoxy group; Aryl group; And substituted with one substituent selected from the group consisting of a heteroaryl group, substituted with a substituent to which two or more substituents selected from the group are connected, or unsubstituted with any substituent. For example, the heteroarylaryl group may be an aryl group, and may be interpreted as a substituent connected with a heteroaryl group and an aryl group. Examples of the group to which three substituents are connected include an aryl group substituted with a heteroaryl group substituted with an aryl group, an aryl group substituted with an aryl group substituted with a heteroaryl group, and a heteroaryl group substituted with an aryl group substituted with a heteroaryl group.

In the present specification, examples of the halogen group include a fluoro group, a chloro group, a bromo group, or an iodo group.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 30 carbon atoms. The carbonyl group may be represented by -C(=O)Rm, where Rm is hydrogen having 1 to 25 carbon atoms; A linear, branched or cyclic alkyl group; Or it may be an aryl group having 6 to 25 carbon atoms.

In the present specification, the ester group may be represented by -COORn. The number of carbon atoms of the ester group is not particularly limited, but is preferably 1 to 30 carbon atoms. Wherein Rn is a straight chain, branched chain or cyclic chain alkyl group having 1 to 25 carbon atoms; Or it may be an aryl group having 6 to 25 carbon atoms.

In the present specification, the silyl group may be represented by the formula of -SiRxRyRz, wherein Rx, Ry and Rz are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; Or it may be a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. The silyl group may be, for example, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. Not limited.

In the present specification, -TMS is a trimethylsilyl group.

In the present specification, the alkoxy group refers to a group in which an alkyl group is bonded to an oxygen atom, and the number of carbon atoms is not particularly limited, but 1 to 30; 1 to 20; 1 to 15; 1 to 10; Or it is preferably 1 to 6. Specific examples of the alkoxy group include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, a pentyloxy group, an iso-amyloxy group, and a hexyloxy group.

In the present specification, the haloalkoxy group refers to an alkoxy group substituted with one or more halogen groups, and the above description of the halogen group and the alkoxy group may be applied to the halogen group and the alkoxy group of the haloalkoxy group.

In the present specification, an alkyl group refers to a linear or branched saturated hydrocarbon. The number of carbon atoms of the alkyl group is not particularly limited, but 1 to 30; 1 to 25; 1 to 20; 1 to 15; 1 to 10; Or it is preferably 1 to 6. The alkyl group may be chain or cyclic.

Specific examples of the chain alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl , Isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

The number of carbon atoms of the cyclic alkyl group (cycloalkyl group) is not particularly limited, but is 3 to 30; 3 to 24; 3 to 14; 3 to 8; Or it is preferably 3 to 6. 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 are not limited thereto.

In the present specification, a haloalkyl group refers to an alkyl group substituted with one or more halogen groups, and the foregoing description of the halogen group and the alkyl group may be applied to the halogen group and the alkyl group of the haloalkyl group.

In the present specification, an aryl group means wholly or partially unsaturated substituted or unsubstituted monocyclic or polycyclic. Although the number of carbon atoms is not particularly limited, the number of carbon atoms is 6 to 60; 6 to 40; 6 to 36; 6 to 30; 6 to 25; 6 to 20; Or it is preferably 6 to 18. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, and a terphenyl group. The polycyclic aryl group is a naphthyl group, anthracenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenalenyl group, pyrenyl group, tetracenyl group, chrysenyl group, pentacenyl group , Fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirofluorenyl group, and the like, but are not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

,

,

,

,

,

,

및

등이 있으나, 이에 한정되지 않는다.The substituted fluorenyl group is

,

,

,

,

,

,

And

And the like, but are not limited thereto.

In the present specification, the heteroaryl group is a cyclic group including at least one of N, O, and S as a heteroatom, and the number of carbon atoms is not particularly limited, but the number of carbon atoms is 2 to 40; 2 to 36; 2 to 30; 2 to 25; 2 to 20; Or it is preferably 2 to 16. Examples of the heteroaryl group include thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, tria Genyl group, triazolyl group, acridinyl group, carbonyl group, acenaphthoquinoxalinyl group, indenoquinazolinyl group, indenoisoquinolinyl group, indenoquinolinyl group, pyridoindolyl group, pyridazinyl group, Pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolinyl group, indolyl group, carbazolyl group , Benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, dibenzofuranyl group, phenanthrolinyl group (phenanthrolinyl), thiazolyl Group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenoxazinyl group, phenothiazinyl group, and the like, but are not limited thereto.

The description of the above-described alkyl group may be applied to the alkyl group of the alkyl sulfoxy group.

The description of the aryl group described above may be applied to the aryl group in the arylsulfoxy group.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent located three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the meaning of forming a ring by bonding with adjacent groups to each other means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring of these.

The hydrocarbon ring means a ring consisting of only carbon and hydrogen atoms, and the hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle refers to a ring including one or more of heteroatoms, and the heterocycle may be an aliphatic heterocycle or an aromatic heterocycle.

In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic hetero ring and the aromatic hetero ring may be monocyclic or polycyclic.

The aliphatic hydrocarbon ring is a ring that is not aromatic and refers to a ring consisting only of carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, It is not limited to this.

The aromatic hydrocarbon ring means an aromatic ring consisting only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthalene, benzo Fluorene, spirobifluorene, and the like, but are not limited thereto.

The aliphatic heterocycle means an aliphatic ring containing at least one heteroatom. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephan, and azocaine , Thiocane, and the like, but are not limited thereto.

The aromatic heterocycle means an aromatic ring containing at least one of heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, acridine , Phenanthridine, diazanaphthalene, dryazainden, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo Carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, phenanthridine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

In the exemplary embodiment of the present specification, R1 to R6 and Y1 to Y4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An alkyl group unsubstituted or substituted with a halogen group or a cyano group; An alkoxy group unsubstituted or substituted with a halogen group or a cyano group; An aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen group, a cyano group, a haloalkyl group, and a haloalkoxy group; Or a halogen group or a heteroaryl group unsubstituted or substituted with a cyano group, and at least one of R1 to R6 is a cyano group.

In the exemplary embodiment of the present specification, R1 to R6 and Y1 to Y4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 18 carbon atoms; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with a halogen group or a cyano group; An alkoxy group having 1 to 10 carbon atoms unsubstituted or substituted with a halogen group or a cyano group; An aryl group having 6 to 18 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen group, a cyano group, a haloalkyl group having 1 to 10 carbon atoms, and a haloalkoxy group having 1 to 10 carbon atoms; Or a halogen group or a C2-C18 heteroaryl group unsubstituted or substituted with a cyano group, and at least one of R1 to R6 is a cyano group.

In the exemplary embodiment of the present specification, R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A silyl group substituted with an alkyl group; Haloalkyl group; An aryl group having 6 to 18 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen group, a cyano group, a haloalkyl group, and a haloalkoxy group; Or a 6-membered heteroaryl group containing 1 or more N, and at least one of R1 to R6 is a cyano group.

In the exemplary embodiment of the present specification, R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluoro group; Cyano group; Trimethylsilyl group; A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a fluoro group, a cyano group, a trifluoromethyl group, and a trifluoromethoxy group; Pyrimidinyl group; Diazinyl group; Or a triazinyl group, and at least one of R1 to R6 is a cyano group.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted alkoxy group.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Haloalkyl group; Or a haloalkoxy group.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A haloalkyl group having 1 to 10 carbon atoms; Or a haloalkoxy group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, R1 is hydrogen; Fluoro group; Cyano group; Trifluoromethyl group; Or a trifluoromethoxy group.

In the exemplary embodiment of the present specification, R2 is hydrogen; Fluoro group; Cyano group; Trifluoromethyl group; Or a trifluoromethoxy group.

In the exemplary embodiment of the present specification, R1 and R2 are the same.

In an exemplary embodiment of the present specification, R4 is CN.

In an exemplary embodiment of the present specification, R5 is CN.

In an exemplary embodiment of the present specification, R4 and R5 are the same.

In the exemplary embodiment of the present specification, R3 and R6 are the same as or different from each other, and each independently a substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, R3 and R6 are the same as or different from each other, and each independently a silyl group unsubstituted or substituted with an alkyl group; An aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen group, a haloalkyl group, a haloalkoxy group, and a cyano group; Or it is a heteroaryl group containing 1 or more N.

In the exemplary embodiment of the present specification, R3 and R6 are the same as or different from each other, and each independently a silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 18 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen group, a haloalkyl group having 1 to 10 carbon atoms, a haloalkoxy group having 1 to 10 carbon atoms, and a cyano group; Or it is a C2-C18 heteroaryl group containing a 6-membered ring containing 1 or more N.

In the exemplary embodiment of the present specification, R3 and R6 are the same as or different from each other, and each independently a silyl group unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms; An aryl group having 6 to 12 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen group, a haloalkyl group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, and a cyano group; Or it is a 6-membered heteroaryl group containing 1 or more N.

In the exemplary embodiment of the present specification, R3 and R6 are the same as or different from each other, and each independently a trimethylsilyl group; A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a fluoro group, a trifluoromethyl group, a trifluoromethoxy group, and a cyano group; Pyrimidinyl group; Diazinyl group; Or a triazinyl group.

In the exemplary embodiment of the present specification, R3 and R6 are the same as or different from each other, and each independently a substituted or unsubstituted silyl group; Substituted phenyl group; A substituted or unsubstituted polycyclic aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, R3 and R6 are the same as or different from each other, and each independently a silyl group unsubstituted or substituted with an alkyl group; A phenyl group substituted with one or more substituents selected from the group consisting of a halogen group, a haloalkyl group, a haloalkoxy group, and a cyano group; A polycyclic aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen group, a haloalkyl group, a haloalkoxy group, and a cyano group; Or a substituted or unsubstituted heteroaryl group containing 1 or more N.

In an exemplary embodiment of the present specification, R3 and R6 are the same.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 2.

[Formula 2]

In Formula 2, R1 to R3, R6, and Y1 to Y4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

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

According to an exemplary embodiment of the present specification, the compound of Formula 1 described above may be prepared according to the following General Formula 1. The following general formula 1 shows a method for preparing an exemplary compound of Chemical Formula 1, and other compounds of Chemical Formula 1 may be prepared by changing the type or substitution position of the substituent.

[General Formula 1]

In the general formula 1, the definitions of R1 to R6 and Y1 to Y4 are the same as those defined in Chemical Formula 1, and G1 is a halogen group or -OTF (trifluoromethoxy group).

Referring to the general formula (1), introducing a group which contains the R6 and R3 via a common sonogashira coupling reaction to the reaction and introducing a ketone through the oxidation and ring-forming reaction and then, through the underlying S _N 2 reaction Y1 to Y4 may be finally introduced to prepare a compound according to an exemplary embodiment of Chemical Formula 1.

In addition, the present specification provides an organic light-emitting device including the compound represented by Formula 1 above.

An exemplary embodiment of the present specification is a cathode; anode; And an organic material layer provided between the cathode and the anode, wherein the compound represented by Formula 1 is included in the organic material 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 multilayer structure in which two or more organic material layers are stacked.

In the exemplary embodiment of the present specification, the organic material layer is a hole injection layer, a hole transport layer, a layer that simultaneously injects and transports holes, a hole control layer, a light emitting layer, an electron control layer, a layer that simultaneously injects and transports electrons, an electron transport layer, and And one or more layers selected from the group consisting of electron injection layers. However, the structure of the organic light emitting device is not limited thereto and may include various organic material layers.

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

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is preferably included in at least one of a hole transport layer, a hole injection layer, a layer for simultaneously injecting and transporting holes, and a hole control layer.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is preferably included in a hole transport layer, a hole injection layer, a layer that simultaneously injects and transports holes, or a hole control layer.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is included in the hole transport layer. In an exemplary embodiment, the compound represented by Formula 1 may be included in the hole transport layer of the first layer, or may be included in the hole transport layer of two or more layers, respectively. When the compound represented by Formula 1 is included in each of two or more hole transport layers, each of the compounds represented by Formula 1 may be the same or different.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is included in the hole injection layer. In an exemplary embodiment, the compound represented by Formula 1 may be included in the hole injection layer of the first layer, or may be included in the hole injection layer of two or more layers, respectively. When the compound represented by Formula 1 is included in each of the two or more hole injection layers, the compounds represented by Formula 1 may be the same or different.

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, and a light emitting layer, as shown in FIG. (8), the electron transport layer 9, the electron injection layer 10 and may be made of a cathode (4). In an exemplary embodiment, the compound of Formula 1 is included in any one of the hole injection layer 5, the hole transport layer 6, and the hole control layer 7, preferably the hole injection layer 5 .

An exemplary embodiment of the present specification is also a cathode; anode; At least two light emitting units provided between the cathode and the anode; And a charge generating layer provided between at least two of the two or more light emitting units, wherein the compound represented by Formula 1 is included in the charge generating layer. do.

The tandem type organic light emitting device has a structure in which two or more light emitting units are stacked. Since the device of the tandem structure can be driven at a lower current than the unit device based on the same brightness, there is an advantage in that the lifespan characteristics of the device are greatly improved.

In the tandem type organic light-emitting device, each light-emitting unit may include at least one light-emitting layer, and may further include an organic material layer other than the light-emitting layer. In one embodiment, each of the light emitting units is independently a hole injection layer, a hole transport layer, a layer that simultaneously injects and transports holes, a hole control layer, an electron control layer, a layer that simultaneously injects and transports electrons, an electron transport layer, and It further includes at least one layer selected from the group consisting of electron injection layers.

In the present specification, a charge generating layer refers to a layer in which holes and electrons are generated when a voltage is applied. The charge generation layer includes an N-type charge generation layer and a P-type charge generation layer. In the present specification, the N-type charge generation layer refers to a charge generation layer located closer to the anode than the P-type charge generation layer, and the P-type charge generation layer refers to a charge generation layer located closer to the cathode than the N-type charge generation layer.

In the exemplary embodiment of the present specification, the charge generation layer includes an N-type charge generation layer and a P-type charge generation layer, and the compound represented by Formula 1 is included in the P-type charge generation layer.

The N-type charge generation layer and the P-type charge generation layer may be provided in contact with each other, and in this case, an NP junction is formed. By the NP junction, holes are easily formed in the P-type charge generation layer and electrons are easily formed in the N-type charge generation layer. Electrons are transported toward the anode through the LUMO level of the N-type charge generating layer, and holes are transported toward the cathode through the HOMO level of the P-type charge generating layer.

The organic light-emitting device according to an exemplary embodiment of the present invention generates a substrate 1, an anode 2, a first light-emitting unit 11, an N-type charge generation layer 12, and a P-type charge, as shown in FIG. 3. The layer 13, the second light emitting unit 14, and the cathode 4 may be formed. In the device structure as shown in FIG. 3, the P-type charge generation layer 13 may include a compound represented by Formula 1 above.

In the exemplary embodiment of the present specification, the organic light emitting device of FIG. 3 includes a substrate, an anode, and a first light emitting unit (a first hole injection layer, a first hole transport layer, a first hole control layer, a first emission layer, and a first electron). A transport layer), an N-type charge generation layer, a P-type charge generation layer, a second light-emitting unit (a second hole transport layer, a second light-emitting layer, and a second electron transport layer), and a cathode, but are not limited thereto.

3 illustrates a tandem type organic light emitting device including two light emitting units, the tandem type organic light emitting device may have an appropriate number of light emitting units as necessary, and the upper limit of the number is not particularly limited.

The N-type charge generation layer is 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorine-substituted 3,4,9,10-pe Rylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenylline derivative And the like, but is not limited thereto. In one embodiment, the N-type charge generation layer may include a benzoimidazophenanthrinine derivative and a metal of Li at the same time.

The P-type charge generation layer may include an arylamine derivative and a compound containing a cyano group at the same time.

In an exemplary embodiment of the present specification, the organic material layer including Formula 1 further includes a compound represented by Formula 3-A or Formula 3-B.

[Formula 3-A]

In Formula 3-A,

R11 and R12 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, or combine with each other to form a substituted or unsubstituted ring,

R13 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

a13 is an integer from 0 to 6, and when a13 is 2 or more, R13 is the same as or different from each other,

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

Ar3 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group,

[Formula 3-B]

In Formula 3-B,

Ar4 is a substituted or unsubstituted aryl group,

L is a substituted or unsubstituted arylene group,

n is an integer of 1 to 4, when n is 2 or more, L is the same as or different from each other,

Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 may include 5 parts by weight to 100 parts by weight based on 100 parts by weight of the organic material layer comprising Formula 1; Alternatively, it is included in the organic material layer in an amount of 5 parts by weight to 95 parts by weight.

In an exemplary embodiment of the present specification, the organic material layer including the compound represented by Formula 1 may include a hole injection layer; Hole transport layer; Hole injection and transport layer; Hole control layer; Alternatively, it may be a p-type charge generation layer, but is not limited thereto.

In an exemplary embodiment of the present specification, the organic material layer including the compound represented by Formula 1 may include a hole injection layer; Or a p-type charge generating layer.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is included in the hole transport layer in an amount of 5 parts by weight to 95 parts by weight based on 100 parts by weight of the hole transport layer including Formula 1.

In the exemplary embodiment of the present specification, R11 and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl group; Or an aryl group unsubstituted or substituted with an alkyl group or an aryl group, or combine with each other to form a ring unsubstituted or substituted with an alkyl group or an aryl group.

In the exemplary embodiment of the present specification, R11 and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms; Or an aryl group having 6 to 25 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 25 carbon atoms, or combined with each other to be substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 25 carbon atoms Formed aromatic hydrocarbon rings.

In the exemplary embodiment of the present specification, R11 and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 6 carbon atoms; Or an aryl group having 6 to 18 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 18 carbon atoms, or substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 18 carbon atoms by bonding to each other To form an aromatic hydrocarbon ring having 6 to 24 carbon atoms.

In the exemplary embodiment of the present specification, R11 and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Or a methyl group, t-butyl group, or a phenyl group unsubstituted or substituted with a phenyl group, or combine with each other to form a fluorene ring.

In the exemplary embodiment of the present specification, R13 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

In the exemplary embodiment of the present specification, R13 is hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms; Or an aryl group unsubstituted or substituted with an alkyl group or an aryl group.

In the exemplary embodiment of the present specification, R13 is hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms; Or an aryl group having 6 to 25 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 25 carbon atoms.

In the exemplary embodiment of the present specification, R13 is hydrogen; heavy hydrogen; Alkyl group; Or a phenyl group unsubstituted or substituted with an alkyl group or an aryl group.

In the exemplary embodiment of the present specification, R13 is hydrogen; Methyl group; t-butyl group; Or a phenyl group.

In the exemplary embodiment of the present specification, a13 is 1.

In the exemplary embodiment of the present specification, a13 is 0.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 25 carbon atoms; Or a substituted or unsubstituted C2 to C25 heteroaryl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; Or an alkyl group, an aryl group, or a heteroaryl group unsubstituted or substituted with a heteroaryl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 25 carbon atoms, or a heteroaryl group having 2 to 25 carbon atoms Aryl group having 6 to 25 carbon atoms; Or a C2-C25 heteroaryl group substituted or unsubstituted with a C1-C10 alkyl group, a C6-C25 aryl group, or a C2-C25 heteroaryl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted tetraphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a carbazolyl group, a phenalthrenyl group, a dibenzofuranyl group, and a dibenzothio group. A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group; A biphenyl group unsubstituted or substituted with a phenyl group; A terphenyl group unsubstituted or substituted with a phenyl group or a biphenyl group; Tetraphenyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; 9,9'-spirobifluorenyl group; Naphthyl group; Triphenylenyl group; Phenanthrenyl group; Dibenzofuranyl group; Or a dibenzothiophenyl group.

In the exemplary embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

In the exemplary embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; Or an aryl group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; Or a C6-C25 aryl group substituted or unsubstituted with a C6-C25 aryl group.

In the exemplary embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; Or it is a C6-C18 aryl group substituted or unsubstituted with a C6-C18 aryl group.

In the exemplary embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

In the exemplary embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; Phenyl group; Biphenyl group; Or a naphthyl group.

In the exemplary embodiment of the present specification, Ar4 is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

In the exemplary embodiment of the present specification, Ar4 is an aryl group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, Ar4 is an aryl group having 6 to 25 carbon atoms, which is unsubstituted or substituted with an aryl group having 6 to 25 carbon atoms.

In the exemplary embodiment of the present specification, Ar4 is an aryl group having 6 to 18 carbon atoms, which is unsubstituted or substituted with an aryl group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, Ar4 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In the exemplary embodiment of the present specification, Ar4 is a phenyl group; Biphenyl group; Or a naphthyl group.

In the exemplary embodiment of the present specification, Ar4 is a phenyl group; [1,1'-biphenyl]-4-yl group; Or 1-naphthyl group.

In the exemplary embodiment of the present specification, L is a substituted or unsubstituted arylene group having 6 to 25 carbon atoms.

In the exemplary embodiment of the present specification, L is a substituted or unsubstituted arylene group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, L is a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

In the exemplary embodiment of the present specification, L is an arylene group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, L is an arylene group.

In the exemplary embodiment of the present specification, L is an arylene group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, L is a phenylene group; Or a biphenylene group.

In the exemplary embodiment of the present specification, n is 1.

In the exemplary embodiment of the present specification, n is 2.

In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and are each independently an aryl group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and are each independently an aryl group having 6 to 25 carbon atoms substituted or unsubstituted with an aryl group having 6 to 25 carbon atoms.

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

In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group; Biphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; A fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; Or a 9,9'-spirobifluorenyl group.

In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a phenyl group or a phenyl group unsubstituted or substituted with a naphthyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Or a 9,9'-spirobifluorenyl group.

In the exemplary embodiment of the present specification, the compound represented by Formula 3-A is any one selected from the following compounds.

In an exemplary embodiment of the present invention, the compound represented by Formula 3-B is any one selected from the following compounds.

According to an exemplary embodiment of the present specification, the compound of Formula 3-A described above may be prepared according to the following General Formula 3-A.

[General Formula 3-A]

A halogen group (X) is introduced into the reactant using a general halogenation reaction, and then an Ar3 group is introduced through a C-C coupling reaction such as a Suzuki reaction. Thereafter, an Ar1 or Ar2 group is introduced into the amine group through a Buchwald reaction. In the general formula 3-A, the definitions of R11, R12, and Ar1 to Ar3 are the same as those defined in the general formula 3-A.

According to an exemplary embodiment of the present specification, the compound of Formula 3-B described above may be prepared according to the following General Formula 3-B.

[General Formula 3-B]

Ar6 groups may be introduced into the amine group through a general Buchwald reaction, and then the amine groups may be introduced into carbazole through an additional Buchwald reaction. In the general formula 3-B, the definitions of Ar4 to Ar6, L and n are the same as those defined in the general formula 3-B, and Y is a halogen group.

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.

In addition, the organic light-emitting device of the present specification may have the following stacked structure, but is not particularly 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 injection layer/hole transport layer/light emitting layer/electron transport layer/cathode

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

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

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

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

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

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

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

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

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 the compound of Formula 1 above.

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

In addition, the compound of Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

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

In the exemplary embodiment of the present specification, when the compound of Formula 1 is included in the one or more organic material layers, materials other than the compound of Formula 1 may be the same or different from each other. When the organic light emitting device includes a plurality of organic material layers, the plurality of organic material layers may be formed of the same material or different materials.

As the anode material, it is preferable to use a material having a large work function 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); Combinations of metals and oxides 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.

As the cathode material, it is preferable to use 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 are multilayered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer for injecting holes received from an electrode into an adjacent layer. The hole injection material has the ability to transport holes 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 transfer of 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 is excellent in thin film formation ability. It is preferable that the HOMO (highest occupied molecular orbital) 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 material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene. There are a series of organic substances, anthraquinone, and polyaniline and a polythiophene series of conductive polymers, but are not limited thereto.

The hole transport layer is a layer that transports holes injected from the hole injection layer to the emission layer. As the hole transport material, a material capable of transporting holes from an anode or a hole injection layer to the light emitting layer and having high mobility for holes is suitable. Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion.

The hole control layer is a layer that prevents excess electrons passing through the emission layer from moving in the direction of the hole transport layer. The hole control material is preferably a material having a lower LUMO (Lowest Unoccupied Molecular Orbital) level than the transport transport layer, and may be selected as an appropriate material in consideration of the energy level of the surrounding layer. In an exemplary embodiment, an arylamine-based organic material may be used as the hole control layer, but is not limited thereto.

The electron control layer is a layer that blocks the inflow of holes from the emission layer to the cathode and controls the electrons flowing into the emission layer to control the performance of the entire device. The electron controlling material is preferably a compound having the ability to prevent the inflow of holes from the light-emitting layer to the cathode and to control electrons injected into the light-emitting layer or the light-emitting material. As the electron controlling material, a suitable material may be used according to the configuration of the organic material layer used in the device. The electron control layer is located between the light emitting layer and the cathode, and is preferably provided in direct contact with the light emitting layer.

According to an exemplary embodiment of the present specification, the hole transport layer; Hole injection layer; Electron control layer; Hole injection and transport layer; Alternatively, the p-type charge generation layer may further include a p-type dopant. As the p-type dopant, those known in the art may be used, for example, an arylamine derivative and a compound including a cyano group. The p-type dopant includes the hole transport layer; Hole injection layer; Electron control layer; Hole injection and transport layer; Alternatively, it may be included in an amount of 0.1% to 75% by weight, preferably 30% to 55% by weight, based on 100% by weight of the p-type charge generating layer.

In the exemplary embodiment of the present specification, the hole injection and transport layer refers to a layer that simultaneously injects and transports holes. Materials of the above-described hole injection layer and hole transport layer may be used for the hole injection and transport layer.

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. Specific examples of the light-emitting material include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material.

As a host material for the light emitting layer, a condensed aromatic ring derivative or a heterocyclic-containing compound may be used. The condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocycle-containing 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, periflanthene and the like having an arylamine group may 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, and styryltetraamine. As the metal complex, an iridium complex, a platinum complex, or the like may be used, but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is suitable. Examples of the electron transport material include an 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 negative electrode material as used according to the prior art. In an exemplary embodiment, as the negative electrode material, a material having a low work function; And an aluminum layer or a silver layer. Examples of the material having the 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 for injecting electrons received from an 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 on the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the hole injection layer, In addition, it is preferable to use a compound excellent in thin film forming ability. 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.

In the exemplary embodiment of the present specification, the electron injection and transport layer refers to a layer that simultaneously injects and transports electrons. Materials of the electron injection layer and the electron transport layer described above may be used for the electron injection and transport layer.

According to an exemplary embodiment of the present specification, the electron transport layer; Electron injection layer; Electron control layer; Electron injection and transport layer; Alternatively, the n-type charge generation layer may further include an n-type dopant. As the n-type dopant, those known in the art may be used, and for example, an alkali metal, an alkaline earth metal, an alkali metal compound, an alkaline earth metal compound, an alkali metal complex or an alkaline earth metal complex may be used. As the metal compound, an oxide, a halide, or the like may be used, and the complex may further include an organic ligand. For example, LiQ or the like can be used. The n-type dopant includes the electron transport layer; Electron injection layer; Electron control layer; Electron injection and transport layer; Alternatively, it may be included in an amount of 0.1% to 75% by weight, preferably 30% to 55% by weight, based on 100% by weight of the n-type charge generating layer.

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.

The preparation of the compound represented by Formula 1 and the organic light-emitting device including the same will be described in detail in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

<Production Example 1> Synthesis of Compound 1

Step 1) Synthesis of Compound 1-1

In a 1000 ml round bottom flask 2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile (2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile) (50 g, 0.1592 mol), copper iodide (3.03 g, 1.592 mmol), isopropylamine (89.27 ml, 63.7 mmol) and tetrakis (triphenylphosphine) palladium (0) (7.3 g, 0.634mmol) was added and dissolved in toluene (500ml), followed by heating and stirring. After heating for 10 minutes, 1-ethynyl-3,5-bis (trifluoromethyl) benzene (1-ethynyl-3,5-bis (trifluoromethyl) benzene) (112.71 g, 0.3981 mol) was added to toluene (100 ml). Melt and slowly add dropwise.

After the reaction was completed, 80% of toluene was distilled, and anhydrous ethanol was added thereto to solidify. After filtering and dissolving in chloroform, the mixture is stirred with water for 10 minutes. The organic layer is collected, dried over anhydrous magnesium sulfate, and filtered. The organic layer was distilled under reduced pressure, solidified with anhydrous ethanol, and filtered to obtain compound 1-1 (60 g, yield 60%).

MS[M+H] ⁺ = 628

Step 2) Synthesis of Compound 1-2

In a 500 ml round bottom flask, compound 1-1 (30 g, 0.0477 mol), palladium chloride (PdCl ₂ ) (1.7 g, 0.953 mmol), silver hexafluoroantimonate (AgSbF ₆ ) (3.27 g, 0.953 mmol) and D. Phenyl sulfoxide (Ph ₂ SO) (57.8 g, 0.2859 mol) was dissolved in dichloroethylene (DCE), stirred at 60° C. for 12 hours, then cesium carbonate (Cs ₂ CO ₃ ) (9.532 mmol) was added and stirred for 12 hours. Let it. After extracting with dichloromethane (CH ₂ Cl ₂₎ After completion of the reaction dichloromethane (CH ₂ Cl ₂₎ to all into a 35% hydrochloric acid (HCl) and stirred for 2 hours after the shot. After extraction with dichloromethane/ammonium chloride aqueous solution (CH ₂ Cl ₂ /aq.NH ₄ Cl), the organic layer was dried over anhydrous magnesium sulfate (MgSO ₄ ), and the organic layers were collected and concentrated under reduced pressure. Then, compound 1-2 (15g, yield 45.27%) is obtained using column chromatography.

MS[M+H] ⁺ = 656

Step 3) Synthesis of Compound 1

Compound 1-2 (10g, 0.01523mol), malononitrile (3.046mmol) and dichloromethane solvent were added to a 500ml round bottom flask and stirred for 30 minutes under argon conditions. After cooling to 0℃ and stirring for 10 minutes, titanium tetrachloride (TiCl ₄ ) (8.45ml, 6.092mol) was slowly added, pyridine (7.35ml, 9.138mmol) was added, and the temperature was slowly raised to room temperature at 0℃ for 2 hours at room temperature. Stir. After extraction with dichloromethane/ammonium chloride aqueous solution (CH ₂ Cl ₂ /aq.NH ₄ Cl), the organic layer was dried over anhydrous magnesium sulfate, and the organic layer was collected and distilled under reduced pressure. 43.66%).

MS[M+H] ⁺ = 752

<Production Example 2> Synthesis of Compound 2

Step 1) Synthesis of compound 2-1

In a 1000 ml round bottom flask 2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile (2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile) (50 g, 15.87 mmol), copper iodide (3.03 g, 1.592 mmol), isopropylamine (89.27 ml, 63.70 mmol) and tetrakis (triphenylphosphine) palladium (0) (7.3 g, 0.634 mmol), dissolved in toluene (500ml), and stirred with heating. After heating and stirring for 10 minutes, 4-ethynyl-2-(trifluoromethyl)benzonitrile) (92.6g, 0.4746mol) is dissolved in toluene (100ml) and slowly added dropwise. . After the reaction was completed, 80% of toluene was distilled, and anhydrous ethanol was added thereto to solidify. After filtering and dissolving in chloroform, the mixture is stirred with water for 10 minutes. The organic layer is collected, dried over anhydrous magnesium sulfate, and filtered. The organic layer was distilled under reduced pressure, solidified with anhydrous ethanol, and filtered to obtain compound 2-1 (40 g, yield 46.28%).

MS[M+H] ⁺ = 542

Step 2) Synthesis of Compound 2

Compound 2-2 was prepared in the same manner as the synthesis method of compound 1-2, except that compound 2-1 was used instead of compound 1-1. Thereafter, compound 2 (3.9g, yield: 66%) was prepared in the same manner as the synthesis method of compound 1, except that compound 2-2 was used instead of compound 1-2.

MS[M+H] ⁺ = 666

<Production Example 3> Synthesis of Compound 3

Step 1) Synthesis of compound 3-1

In a 1000 ml round bottom flask 2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile (2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile) (50 g, 15.87 mmol), copper iodide (3.03 g, 1.592 mmol), isopropylamine (89.27 ml, 63.70 mmol) and tetrakis (triphenylphosphine) palladium (0) (7.3 g, 0.634 mmol), dissolved in toluene (500ml), and stirred with heating. After heating and stirring for 10 minutes, 4-ethynyl-2,6-difluorobenzonitrile (77.4 g, 0.4746 mol) is dissolved in toluene (100 ml) and slowly added dropwise. After completion of the reaction, 80% of toluene was distilled, and then anhydrous ethanol was added to solidify. After filtering and dissolving in chloroform, the mixture is stirred with water for 10 minutes. The organic layer is collected, dried over anhydrous magnesium sulfate, and filtered. The organic layer was distilled under reduced pressure, solidified with anhydrous ethanol, and filtered to obtain compound 3-1 (35 g, yield 46%).

MS[M+H] ⁺ = 478

Step 2) Synthesis of compound 3

Compound 3-2 was prepared in the same manner as the synthesis method of compound 1-2, except that compound 3-1 was used instead of compound 1-1. Thereafter, compound 3 (3.3g, yield 72%) was prepared in the same manner as in the synthesis method of compound 1, except that compound 3-2 was used instead of compound 1-2.

MS[M+H] ⁺ = 602

<Production Example 4> Synthesis of Compound 4

Step 1) Synthesis of compound 4-1

In a 1000 ml round bottom flask 2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile (2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile) (50 g, 15.87 mmol), copper iodide (3.03 g, 1.592 mmol), isopropylamine (89.27 ml, 63.70 mmol) and tetrakis (triphenylphosphine) palladium (0) (7.3 g, 0.634 mmol), dissolved in toluene (500ml), and stirred with heating. After heating and stirring for 10 minutes, 4-ethynlphtalonitrile (72.5g 0.4746mmol) is dissolved in toluene (100ml) and slowly added dropwise. After the reaction was completed, 80% of toluene was distilled, and anhydrous ethanol was added thereto to solidify. After filtering and dissolving in chloroform, the mixture is stirred with water for 10 minutes. The organic layer is collected, dried over anhydrous magnesium sulfate, and filtered. The organic layer was distilled under reduced pressure, solidified with anhydrous ethanol, and filtered to obtain compound 4-1 (35 g, yield 48.16%).

MS[M+H] ⁺ = 456

Step 2) Synthesis of compound 4

Compound 4-2 was prepared in the same manner as the synthesis method of compound 1-2, except that compound 4-1 was used instead of compound 1-1. Thereafter, compound 4 (3.3g, yield 72%) was prepared in the same manner as the synthesis method of compound 1, except that compound 4-2 was used instead of compound 1-2.

MS[M+H] ⁺ = 580

<Production Example 5> Synthesis of Compound 5

2,2' instead of 2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile (2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile) -(3,6-dibromo-4,5-bis(trifluoromethoxy)-1,2-phenylene)diacetonitrile is used, and 1-ethynyl-3,5-bis(trifluoro Compound 5-1 was synthesized in the same manner as in the synthesis method of compound 1-1, except that 5-ethynylpyrimidine was used instead of methyl)benzene.

Compound 5-2 was synthesized in the same manner as the synthesis method of compound 1-2, except that compound 5-1 was used instead of compound 1-1.

Compound 5 (3g, yield 51%) was synthesized in the same manner as in the synthesis method of compound 1, except that compound 5-2 was used instead of compound 1-2.

MS[M+H] ⁺ = 653.44

<Production Example 6> Synthesis of Compound 6

2,2' instead of 2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile (2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile) -(3,6-dibromo-4,5-difluoro-1,2-phenylene)diacetonitrile is used, instead of 1-ethynyl-3,5-bis(trifluoromethyl)benzene Compound 6-1 was synthesized in the same manner as the synthesis method of compound 1-1, except that ethynyltrimethylsilane was used.

Compound 6-2 was synthesized in the same manner as the synthesis method of compound 1-2, except that compound 6-1 was used instead of compound 1-1.

Compound 6 (8g, yield 65%) was synthesized in the same manner as in the synthesis method of compound 1, except that compound 6-2 was used instead of compound 1-2.

MS[M+H] ⁺ = 509.11

<Production Example 7> Synthesis of Compound 7

3,6- instead of 2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile (2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile) Dibromo-4,5-bis(cyanomethyl)phthalonitrile is used, and 1-ethynyl-4-methoxybenzene is used instead of 1-ethynyl-3,5-bis(trifluoromethyl)benzene. Except for using, compound 7-1 was synthesized in the same manner as in the synthesis method of compound 1-1.

Compound 7-2 was synthesized in the same manner as the synthesis method of compound 1-2, except that compound 7-1 was used instead of compound 1-1.

Compound 7 (4g, yield 49.3%) was synthesized in the same manner as in the synthesis method of compound 1, except that compound 7-2 was used instead of compound 1-2.

MS[M+H] ⁺ = 699.07

<Production Example 8> Synthesis of Compound B

2,2' instead of 2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile (2,2'-(3,6-dibromo-1,2-phenylene)diacetonitrile) -(3,6-dibromo-1,2-phenylene)diacetonitrile was used, except that ethynylbenzene was used instead of 1-ethynyl-3,5-bis(trifluoromethyl)benzene Was synthesized compound B-1 in the same manner as the synthesis method of compound 1-1.

Compound B-2 was synthesized in the same manner as the synthesis method of compound 1-2, except that compound B-1 was used instead of compound 1-1.

Compound B (8g, yield 64%) was synthesized in the same manner as in the synthesis method of compound 1, except that compound B-2 was used instead of compound 1-2.

MS[M+H] ⁺ = 481

<Device example>

<Example 1-1>

A glass substrate coated with a thin film of ITO (Indium Tin Oxide) having a thickness of 140 nm was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a Decon™ CON705 product of Fischer Co. was used as a detergent, and distilled water secondarily filtered with a 0.22 μm sterilizing 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 was finished, ultrasonic cleaning was performed for 10 minutes with a solvent of isopropyl alcohol, acetone, and methanol, and dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, the following Compound HT-A and Compound 1 were thermally vacuum deposited to a thickness of 10 nm at a weight ratio of 95:5 to form a hole injection layer, and then Compound HT-A material was deposited to a thickness of 110 nm to form a hole transport layer. Formed. The following compound EB-A was thermally vacuum deposited to a thickness of 5 nm as a hole control layer thereon. Subsequently, the following compound BH-A and the following BD-A were vacuum-deposited to a thickness of 20 nm in a weight ratio of 96:4 as a light emitting layer. Subsequently, a compound represented by ET-A and Liq as an electron transport layer was thermally vacuum deposited to a thickness of 36 nm at a weight ratio of 1:1, and then a compound represented by the following Liq was vacuum-deposited to a thickness of 0.5 nm to form an electron injection layer. I did. An organic light-emitting device was manufactured by sequentially depositing magnesium and silver on the electron injection layer at a weight ratio of 10:1 to a thickness of 22 nm and aluminum to a thickness of 100 nm to form a cathode.

<Example 1-2> to <Example 1-8>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compounds shown in Table 1 were used instead of Compound 1 in Example 1-1.

<Comparative Example 1-1>

An organic light-emitting device in the same manner as in Example 1-1, except that the following compound HAT-CN was used instead of the compound HT-A and compound 1 in a weight ratio of 95:5 as the hole injection layer in Example 1-1. Was produced.

[HAT-CN]

<Comparative Example 1-2>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the hole injection layer was formed without any doping instead of Compound 1 in Example 1-1.

<Comparative Example 1-3>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound A was used instead of Compound 1 in Example 1-1.

Table 1 shows driving voltages and current efficiencies of the organic light emitting devices prepared in Examples 1-1 to 1-8 and Comparative Examples 1-1 to 1-3. At this time, voltage and efficiency were measured by applying a current density ^{of 10 mA/cm 2.}

Hole injection layer material Voltage
(V) efficiency
(cd/A) Example 1-1 Compound 1 + HT-A 4.79 6.20 Example 1-2 Compound 2 + HT-A 4.68 6.35 Example 1-3 Compound 3 + HT-A 4.60 6.50 Example 1-4 Compound 4 + HT-A 4.49 6.80 Example 1-5 Compound 5 + HT-A 4.42 6.90 Example 1-6 Compound 6 + HT-A 4.40 6.91 Example 1-7 Compound 7 + HT-A 4.30 6.98 Example 1-8 Compound B + HT-A 5.52 5.18 Comparative Example 1-1 Compound HAT-CN 6.23 4.88 Comparative Example 1-2 Compound HT-A 8.7 2.03 Comparative Example 1-3 Compound A + HT-A 6.28 3.85

It was confirmed from Table 1 that a device including the compound represented by Formula 1 of the present invention in an organic material layer, particularly a hole injection layer, has improved driving voltage and efficiency.

<Example 2-1>

A glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 100 nm was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the prepared ITO transparent electrode, HAT-CN was thermally vacuum deposited to a thickness of 5 nm to form a hole injection layer, followed by vacuum deposition of the compound NPB to a thickness of 10 nm to form a first hole transport layer. Subsequently, the following compound EB-B was vacuum-deposited on the first hole transport layer with a thickness of 10 nm to form a first hole control layer. Subsequently, compounds YGH-A, YGH-B, and YGD were vacuum-deposited at a weight ratio of 2:2:1 with a film thickness of 40 nm on the first hole control layer to form a first emission layer. Subsequently, the compound ET-B was vacuum-deposited to a thickness of 25 nm on the first emission layer to form a first electron transport layer. Subsequently, the following compounds NCG and Li (Lithium) were vacuum-deposited at a weight ratio of 50:1 on the first electron transport layer to form an N-type charge generation layer with a thickness of 10 nm.

Subsequently, HT-A and Compound 1 were vacuum-deposited at a weight ratio of 70:30 to form a P-type charge generation layer with a thickness of 10 nm, and only HT-A was vacuum-deposited to a thickness of 80 nm to form a second hole transport layer. . Subsequently, compounds BH-B and BD-B were vacuum-deposited to a thickness of 25 nm in a weight ratio of 96:4 as the second emission layer.

On the second emission layer, the compound ET-A and Liq as a second electron transport layer were thermally vacuum deposited to a thickness of 30 nm at a weight ratio of 1:1, and then LiF (Lithium Fluoride) was vacuum deposited to a thickness of 1 nm and aluminum to a thickness of 80 nm By forming a cathode, an organic light emitting device was manufactured.

<Example 2-2> to <Example 2-15>

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that the compounds shown in Table 2 were used instead of Compound 1 and HT-A in Example 2-1.

<Comparative Example 2-1> to <Comparative Example 2-6>

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that Compound 1 and HT-A in Example 2-1, and the compounds shown in Table 2 were used instead.

Table 2 shows the driving voltage and current efficiency of the organic light-emitting devices prepared in Examples 2-1 to 2-15 and Comparative Examples 2-1 to 2-6. At this time, the voltage and efficiency were measured by applying a current density ^{of 10mA/cm 2.}

P-type charge generation layer
Doping material P-type charge generation layer
Hole transport material Voltage
(V) efficiency
(cd/A) Example 2-1 Compound 1 Compound HT-A 7.86 67.42 Example 2-2 Compound 2 Compound HT-A 7.84 67.53 Example 2-3 Compound 3 Compound HT-A 7.77 69.02 Example 2-4 Compound 4 Compound HT-A 7.68 69.20 Example 2-5 Compound 1 Compound HT-B 7.97 67.42 Example 2-6 Compound 2 Compound HT-B 8.03 66.04 Example 2-7 Compound 3 Compound HT-B 8.00 65.43 Example 2-8 Compound 4 Compound HT-B 7.99 65.88 Example 2-9 Compound 1 Compound HT-C 7.82 67.97 Example 2-10 Compound 2 Compound HT-C 7.75 68.88 Example 2-11 Compound 3 Compound HT-C 7.74 69.23 Example 2-12 Compound 4 Compound HT-C 7.70 69.42 Experimental Example 2-13 Compound B Compound HT-A 8.97 61.58 Experimental Example 2-14 Compound B Compound HT-B 8.55 62.01 Experimental Example 2-15 Compound B Compound HT-C 8.01 62.55 Comparative Example 2-1 Compound HAT-CN Compound HT-A 10.52 51.32 Comparative Example 2-2 Compound HAT-CN Compound HT-B 10.77 50.45 Comparative Example 2-3 Compound HAT-CN Compound HT-C 10.79 50.3 Comparative Example 2-4 Compound A Compound HT-A 11.87 48.76 Comparative Example 2-5 Compound A Compound HT-B 11.75 48.55 Comparative Example 2-6 Compound A Compound HT-C 11.77 48.64

From Table 2, it was confirmed that the driving voltage and efficiency of the device were improved even when the compound represented by Formula 1 of the present invention was included in the organic material layer of the tandem organic light emitting device.

1: substrate
2: anode
3: organic material layer
4: cathode
5: hole injection layer
6: hole transport layer
7: hole control layer
8: light-emitting layer
9: electron transport layer
10: electron injection layer
11: first light emitting unit
12: N-type charge generation layer
13: P-type charge generation layer
14: second light emitting unit

Claims (13)

cathode; anode; And an organic material layer provided between the cathode and the anode,
The compound represented by the following Formula 1 is included in the organic material layer,
[Formula 1]

In Formula 1,
R1 to R6 and Y1 to Y4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, and at least one of R1 to R6 is a cyano group,
An organic light-emitting device wherein the organic material layer including the compound represented by Formula 1 further comprises a compound represented by Formula 3-A or Formula 3-B:
[Formula 3-A]

In Formula 3-A,
R11 and R12 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, or combine with each other to form a substituted or unsubstituted ring,
R13 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
a13 is an integer from 0 to 6, and when a13 is 2 or more, R13 is the same as or different from each other,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar3 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group,
[Formula 3-B]

In Formula 3-B,
Ar4 is a substituted or unsubstituted aryl group,
L is a substituted or unsubstituted arylene group,
n is an integer of 1 to 4, when n is 2 or more, L is the same as or different from each other,
Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group. The method according to claim 1, R1 to R6 and Y1 to Y4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An alkyl group unsubstituted or substituted with a halogen group or a cyano group; An alkoxy group unsubstituted or substituted with a halogen group or a cyano group; An aryl group substituted with one or more substituents selected from the group consisting of a halogen group, a cyano group, a haloalkyl group, and a haloalkoxy group; Or a halogen group or a heteroaryl group unsubstituted or substituted with a cyano group, and at least one of R1 to R6 is a cyano group. The organic light-emitting device of claim 1, wherein Formula 1 is represented by the following Formula 2:
[Formula 2]

In Formula 2, R1 to R3, R6, and Y1 to Y4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. The organic light-emitting device of claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:

. delete delete The organic light-emitting device of claim 1, wherein the organic material layer is a hole transport layer, a hole injection layer, a layer that simultaneously injects and transports holes, or a hole control layer. cathode; anode; At least two light emitting units provided between the cathode and the anode; And a charge generation layer provided between at least two light emitting units among the two or more light emitting units,
The compound represented by Formula 1 according to claim 1 is included in the charge generating layer,
The charge generation layer including the compound represented by Formula 1 further comprises a compound represented by Formula 3-A or Formula 3-B according to claim 1. cathode; anode; At least two light emitting units provided between the cathode and the anode; And a charge generation layer provided between at least two light emitting units among the two or more light emitting units,
The compound represented by Formula 1 according to claim 1 is any one selected from the following compounds,

The organic light emitting device is that the compound is included in the charge generation layer. The organic light-emitting device of claim 8 or 9, wherein the charge generation layer includes an N-type charge generation layer and a P-type charge generation layer, and the compound represented by Formula 1 is included in the P-type charge generation layer. delete The organic light-emitting device of claim 1, wherein the compound represented by Formula 3-A is any one selected from the following compounds:

. The organic light-emitting device of claim 1, wherein the compound represented by Formula 3-B is any one selected from the following compounds:

.

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