KR20210004868A - 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. The compound may improve lifespan characteristics of the organic light emitting device.

Description

A compound and an organic light-emitting device containing the same TECHNICAL FIELD

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2019-0081385 filed with the Korean Intellectual Property Office on July 5, 2019, the entire contents of which are incorporated herein.

The present specification relates to a compound and an organic light emitting device including the same.

An organic light-emitting device is a light-emitting device using an organic semiconductor material, and requires exchange of holes and/or electrons between an electrode and an organic semiconductor material. The organic light emitting device can be divided into two types as follows according to the operating principle. First, excitons are formed in the organic material layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes, and used as a current source (voltage source). It is a type of light emitting device. The second is a light emitting device in which holes and/or electrons are injected into an organic semiconductor material layer forming an interface with the electrode by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy 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 is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device. For example, a hole injection layer, a hole transport layer, a light emitting layer, an electron control layer, a hole control layer, an electron transport layer, and an electron injection. It can be made of layers, etc. 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 back to the ground. These organic light emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

Materials used as the organic material layer in the organic light-emitting device may be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, electron injection materials, and the like, according to their functions. The light-emitting material includes blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary to realize better natural colors according to the light-emitting color.

In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The principle is that when a small amount of a dopant having an energy band gap smaller than that of a host that mainly constitutes the light emitting layer is mixed with the light emitting layer, excitons generated from the host are transported as a dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

In order to fully exhibit the excellent characteristics of the organic light emitting device described above, materials that form the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron suppression materials, electron transport materials, electron injection materials, etc., are stable and efficient materials. As it is supported by, the development of new materials is continuously required.

International Patent Application Publication No. 2003-012890

The present specification provides a compound 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,

Y1 is O or S,

X1 to X6 are each independently N or CR,

At least one of X1 to X3; And at least one of X4 to X6 is necessarily N,

L1 to L4 are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar1 to Ar4 are each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

At least three of Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

When all of X1 to X6 are N and all of Ar1 to Ar4 are phenyl groups, at least one of Ar1 to Ar4 is deuterium; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted cycloalkyl group; And a phenyl group substituted with one or more substituents selected from a substituted or unsubstituted alkyl group,

R, R1 and R2 are each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxyl group; Halogen group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; Or a substituted or unsubstituted arylthio group,

a and b are each independently an integer of 1 to 4,

When a or b is each of 2 or more, the substituents in the 2 or more parentheses are the same as or different from each other.

In addition, the present application is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the above-described compound.

When the compound according to the exemplary embodiment of the present application is used in an organic light-emitting device, there is an effect of increasing the luminance of the device, lowering the driving voltage, improving luminous efficiency, and improving life characteristics.

1 shows an example of an organic light emitting device according to an exemplary embodiment of the specification.

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

The present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

Y1 is O or S,

X1 to X6 are each independently N or CR,

At least one of X1 to X3; And at least one of X4 to X6 is necessarily N,

L1 to L4 are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar1 to Ar4 are each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

At least three of Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

When all of X1 to X6 are N and all of Ar1 to Ar4 are phenyl groups, at least one of Ar1 to Ar4 is deuterium; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted cycloalkyl group; And a phenyl group substituted with one or more substituents selected from a substituted or unsubstituted alkyl group,

R, R1 and R2 are each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxyl group; Halogen group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; Or a substituted or unsubstituted arylthio group,

a and b are each independently an integer of 1 to 4,

When a or b is each 2 or more, the substituents in the two or more parentheses are the same as or different from each other.

The compound represented by Chemical Formula 1 may change the performance of electron transport and control through the control of the symmetry of the electron withdrawing group amines and the ability to attract electrons around oxadiazole or thiadiazole. Accordingly, the carrier balance as an organic light-emitting device can be derived for each device. In particular, due to the strong electron attracting ability through the combination of the dimer form of the azine group and oxadiazole or thiadiazole, it has excellent electron transport ability and shows excellent mixing effect even when mixed with an alkali metal complex, so when used in organic light emitting devices. There are effects of increasing the luminance of the device, lowering the driving voltage, improving the luminous efficiency, and improving the life characteristics.

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

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Silyl group; Amine group; Phosphine oxide group; Alkyl group; Cycloalkyl group; Alkenyl group; Alkoxy group; Alkylthio group; Aryl group; It means that it is substituted with one or two or more substituents selected from the group consisting of a sulfonyl group and a heterocyclic group, or is substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are limited thereto. It is not.

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

In the present specification, the alkylthio group may be linear, branched or cyclic. Although the number of carbon atoms of the alkylthio group is not particularly limited, it is preferably 1 to 20 carbon atoms. Specifically, methylthio, ethylthio, n-propylthio, isopropylthio, i-propylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio , Isopentylthio, n-hexylthio, 3,3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio and p-methylbenzylthio, etc. , But is not limited thereto.

In the present specification, the number of carbon atoms of the aryl group is not particularly limited, but may be 6 to 60 or 6 to 30, and the aryl group may be monocyclic or polycyclic.

In the present specification, when the aryl group is a monocyclic aryl group, it may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, it may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysene group, a triphenylenyl group, a fluorenyl group, and the like, but is not limited thereto.

In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent aryl group, and may be selected from the examples of the aryl group described above except that it is a divalent group.

In the present specification, the heteroaryl group is an atom other than carbon and contains one or more heteroatoms, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, Si, and S. have. The number of carbon atoms of the heteroaryl group is not particularly limited, but is preferably 2 to 60 carbon atoms or 2 to 30 carbon atoms. Examples of the heteroaryl group include thiophene group, furan group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, tria Genyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group , Isoquinolinyl group, indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophene group, dibenzothiophene group , Benzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzosilol group, dibenzosilol group, phenanthrolinyl group, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, phenoxazine group And their condensation structures, but are not limited thereto.

In the present specification, the heteroarylene group refers to a heteroaryl group having two bonding positions, that is, a divalent heteroaryl group, and may be selected from the examples of the aforementioned heteroaryl group except that it is a divalent group.

In the present specification, the number of carbon atoms in the amine group is not particularly limited, but is preferably 1 to 30. The amine group may be substituted with the aforementioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof, and specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine Group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group And triphenylamine groups, but are not limited thereto.

In the present specification, the number of carbon atoms of the imide group, the carbonyl group and the ester group is not particularly limited, but it is preferably 1 to 50 carbon atoms.

In the present specification, the nitrogen of the amide group may be substituted with hydrogen, a straight-chain, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

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

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, and styrenyl group, but are not limited thereto.

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

In the present specification, the silyl group is a substituent including Si and the Si atom is directly connected as a radical, represented by -SiR ₁₀₄ R ₁₀₅ R ₁₀₆ , R ₁₀₄ to R ₁₀₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Alkyl group; Alkenyl group; Alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group and phenylsilyl group. It is not limited.

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

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

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

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

In the exemplary embodiment of the present specification, Y1 is S.

In the exemplary embodiment of the present specification, Y1 is O.

In the exemplary embodiment of the present specification, Formula 1 may be represented by any one of Formulas 1-1 to 1-6 below.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-1 to 1-6,

Y1, X1 to X6, L1 to L4, Ar1 to Ar4, R1, R2, a and b are the same as defined in Formula 1 above.

In the compound of Formula 1, an N-containing monocyclic ring is substituted with phenylene bonded to both sides of oxadiazole (or thiadiazole), and the N-containing monocyclic ring is based on oxadiazole (or thiadiazole)- It can be combined in the para, -meta or -ortho direction.

According to an exemplary embodiment of the present specification, when the binding direction of the N-containing monocyclic ring includes the -meta and -ortho directions, the electron transport ability and the energy level of the exciton energy barrier are adjusted to increase the speed of electron injection. I can.

In the exemplary embodiment of the present specification, X1 to X6 are each N.

In an exemplary embodiment of the present specification, at least two of X1 to X3; And at least two of X4 to X6 are each N, and the rest of X1 to X6 except for N are each CR.

In the exemplary embodiment of the present specification, X1 to X3 are each N, two of X4 to X6 are each N, and the other is CR.

In the exemplary embodiment of the present specification, X4 to X6 are each N, two of X1 to X3 are each N, and the other is CR.

In the exemplary embodiment of the present specification, two of X1 to X3 are each N, the other one is CR, two of X4 to X6 are each N, and the other one is CR.

In the exemplary embodiment of the present specification, two of X1 to X3 are each N, the other is CR, one of X4 to X6 is N, and the other two are CR.

In the exemplary embodiment of the present specification, two of X4 to X6 are each N, the other is CR, one of X1 to X3 is N, and the other two are CR.

In the exemplary embodiment of the present specification, one of X1 to X3 is N, the other two are CR, one of X4 to X6 is N, and the other two are CR.

In the exemplary embodiment of the present specification, X1 to X3, X5, and X6 are each N, and X4 is CR.

In the exemplary embodiment of the present specification, X1 to X4 and X6 are each N, and X5 is CR.

In the exemplary embodiment of the present specification, X1 to X5 are each N, and X6 is CR.

In the exemplary embodiment of the present specification, X2 to X6 are each N, and X1 is CR.

In the exemplary embodiment of the present specification, X1, X2, X4, and X5 are each N, and X3 and X6 are each CR.

In the exemplary embodiment of the present specification, X1, X2, X5, and X6 are each N, and X3 and X4 are each CR.

In the exemplary embodiment of the present specification, X2, X3, X5, and X6 are each N, and X1 and X4 are each CR.

In the exemplary embodiment of the present specification, X2 to X5 are each N, and X1 and X6 are each CR.

In the exemplary embodiment of the present specification, X1 to X4 are each N, and X5 and X6 are each CR.

In the exemplary embodiment of the present specification, X1 to X3 and X5 are each N, and X4 and X6 are each CR.

In the exemplary embodiment of the present specification, X1 to X3 and X6 are each N, and X4 and X5 are each CR.

In the exemplary embodiment of the present specification, X3 to X6 are each N, and X1 and X2 are each CR.

In the exemplary embodiment of the present specification, X1 and X4 to X6 are each N, and X2 and X3 are each CR.

In the exemplary embodiment of the present specification, X2 and X4 to X6 are each N, and X1 and X3 are each CR.

In the exemplary embodiment of the present specification, X1, X2, X4, and X5 are each CR, and X3 and X6 are each N.

In the exemplary embodiment of the present specification, X1, X2, X5, and X6 are each CR, and X3 and X4 are each N.

In the exemplary embodiment of the present specification, X2, X3, X5, and X6 are each CR, and X1 and X4 are each N.

In the exemplary embodiment of the present specification, X2 to X5 are each CR, and X1 and X6 are each N.

In the exemplary embodiment of the present specification, X1 to X4 are each CR, and X5 and X6 are each N.

In the exemplary embodiment of the present specification, X1 to X3 and X5 are each CR, and X4 and X6 are each N.

In the exemplary embodiment of the present specification, X1 to X3 and X6 are each CR, and X4 and X5 are each N.

In the exemplary embodiment of the present specification, X3 to X6 are each CR, and X1 and X2 are each N.

In the exemplary embodiment of the present specification, X1 and X4 to X6 are each CR, and X2 and X3 are each N.

In the exemplary embodiment of the present specification, X2 and X4 to X6 are each CR, and X1 and X3 are each N.

In an exemplary embodiment of the present specification, R is hydrogen; Nitrile group; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R is hydrogen; Nitrile group; Or a C ₆ -C ₃₀ aryl group.

In an exemplary embodiment of the present specification, R is hydrogen; Nitrile group; Or a phenyl group.

In an exemplary embodiment of the present specification, Formula 1 may be represented by any one of the following structural formulas.

In the above structural formula,

Y1, L1 to L4, Ar1 to Ar4, R1, R2, a and b are the same as defined in Formula 1 above.

According to an exemplary embodiment of the present specification, L1 to L4 are each independently a direct bond; Or a substituted or unsubstituted C 6 to C 30 arylene group.

According to another exemplary embodiment, the L1 to L4 are each independently a direct bond; Or a substituted or unsubstituted phenylene group.

According to another exemplary embodiment, the L1 to L4 are each independently a direct bond; Or a phenylene group.

In the exemplary embodiment of the present specification, when all of X1 to X6 are N, at least one of Ar1 to Ar4 is not an unsubstituted phenyl group. That is, when all of X1 to X6 are N, Ar1 to Ar4 cannot be unsubstituted phenyl groups at the same time. Here, the unsubstituted phenyl group means a phenyl group having no substituent. These conditions apply to all of the descriptions of Ar1 to Ar4 below, even if there is no separate mention.

According to another exemplary embodiment, when all of X1 to X5 are N and all of Ar1 to Ar4 are phenyl, at least one of Ar1 to Ar4 is deuterium; Nitrile group; A substituted or unsubstituted silyl group having 3 to 30 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; And a phenyl group substituted with one or more substituents selected from a substituted or unsubstituted C1 to C20 alkyl group.

In another exemplary embodiment, when all of X1 to X5 are N and all of Ar1 to Ar4 are phenyl, at least one of Ar1 to Ar4 is deuterium; Nitrile group; Trimethylsilyl group; Cyclopentyl group; Cyclohexyl group; Methyl group; And a phenyl group substituted with one or more substituents selected from tert-butyl group.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In another exemplary embodiment, Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group. The heteroaryl group includes O or S as a heteroatom.

According to another exemplary embodiment, Ar1 to Ar4 are each independently a substituted or unsubstituted 6 to 30 aryl group; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and the substituents are selected from deuterium, a nitrile group, a trialkylsilyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and an alkyl group having 1 to 20 carbon atoms. It may be substituted or unsubstituted with one or more substituents.

According to another exemplary embodiment, Ar1 to Ar4 are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophene group, the substituents are deuterium, nitrile group, trimethylsilyl group, cyclopentyl group, cyclohexyl group, methyl group and tert-butyl group to be substituted or unsubstituted with one or more substituents selected from among I can.

In the exemplary embodiment of the present specification, Ar1 to Ar4 may each independently be represented by any one of the following structural formulas.

In the above structural formula,

Q1 is NRa, CRbRc, O or S,

R3 and R4 are each independently hydrogen; heavy hydrogen; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted cycloalkyl group,

Ra to Rc are each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, and Rb and Rc may be bonded to each other to form a ring,

d4 is an integer from 0 to 4,

d5 is an integer from 0 to 5,

d7 is an integer from 0 to 7,

d9 is an integer from 0 to 9,

e is 1 or 2,

When d4, d5, d7, d9 and e are each 2 or more, the substituents in two or more parentheses are the same as or different from each other,

* Is a position connected to Formula 1 above.

In the exemplary embodiment of the present specification, R3 and R4 are each independently hydrogen; heavy hydrogen; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted cycloalkyl group.

In the exemplary embodiment of the present specification, R3 and R4 are each independently deuterium; Nitrile group; A trialkylsilyl group having 3 to 20 carbon atoms; A cycloalkyl group having 3 to 30 carbon atoms; Or an alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, R3 and R4 are each independently deuterium; Nitrile group; Trimethylsilyl group; Cyclopentyl group; Cyclohexyl group; It is a methyl group or a tert-butyl group.

In the exemplary embodiment of the present specification, Ra to Rc are each independently hydrogen or an alkyl group having 1 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ra to Rc are each independently hydrogen or a methyl group.

In the exemplary embodiment of the present specification, d5 is an integer of 1 to 4.

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

In the exemplary embodiment of the present specification, R1 and R2 are each independently hydrogen; heavy hydrogen; Nitrile group; An alkyl group having 1 to 50 carbon atoms; Or an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R1 and R2 are each independently hydrogen; heavy hydrogen; Nitrile group; An alkyl group having 1 to 10 carbon atoms; Or it is a monocyclic aryl group.

In the exemplary embodiment of the present specification, R1 and R2 are each independently hydrogen; heavy hydrogen; Nitrile group; Methyl group; Propyl group; Or a phenyl group.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 may be any one selected from the following structural formulas.

.

.

The compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described below, and the substituent may be combined by a method known in the art, and the type, position, or number of the substituent is known in the art. Subject to change depending on technology.

In the present specification, "energy level" means the energy level. Therefore, the energy level is interpreted to mean the absolute value of the corresponding energy value. For example, a deep energy level means that the absolute value increases in the negative direction from the vacuum level.

In the present specification, HOMO (highest occupied molecular orbital) means a molecular orbital function (highest occupied molecular orbital) in a region with the highest energy in a region where electrons can participate in binding, and LUMO (lowest unoccupied molecular orbital) Means a molecular orbital function (lowest unoccupied molecular orbital) in which electrons have the lowest energy among the anti-bonding regions, and the HOMO energy level means the distance from the vacuum level to the HOMO. In addition, the LUMO energy level means the distance from the vacuum level to the LUMO.

In the present specification, a bandgap means a difference in energy levels between HOMO and LUMO, that is, a HOMO-LUMO gap.

In addition, the present specification provides an organic light-emitting device including the above-described compound.

An exemplary embodiment of the present application is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

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

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

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

In the exemplary embodiment of the present application, the organic material layer includes one or more electron transport layers, and at least one of the electron transport layers includes the compound.

In the exemplary embodiment of the present application, the organic material layer includes one or more electron controlling layers, and at least one of the electron controlling layers includes the compound.

According to an exemplary embodiment of the present specification, the organic material layer includes an electron transport layer, and the electron transport layer may include 5wt% to 99wt% of the compound based on 100wt% of the electron transport layer, and preferably 10wt% to 30wt% Included in %.

In the exemplary embodiment of the present application, the organic material layer includes an electron controlling layer and an electron transport layer, and the electron controlling layer and the electron transport layer include the compound.

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

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

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

1 is a first electrode (1), hole injection layer (2), hole transport layer (3), hole control layer (4), light emitting layer (5), electron control layer (6), electron transport layer (7), electron injection A structure of an organic light-emitting device in which the layer 8 and the second electrode 9 are sequentially stacked is illustrated. In this structure, the compound is the hole injection layer (2), the hole transport layer (3), the hole control layer (4), the light emitting layer (5), the electron control layer (6), the electron transport layer (7) and the electron injection It may be included in one or more of the layers 8, and specifically, may be included in the electron transport layer and/or the electron control layer.

The organic light-emitting device of the present application 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 the present application, that is, the compound.

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.

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

In 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 the exemplary embodiment of the present application, 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.

The anode is an electrode for injecting holes, and a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer as the anode material.

The cathode is an electrode for injecting electrons, and the cathode material is usually a material having a small work function to facilitate electron injection into the organic material layer.

Specific examples of the cathode 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); ZnO: Al or SnO _2: a combination of a metal and an oxide such as 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.

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.

In the exemplary embodiment of the present specification, the emission layer may include a host and a dopant. In this case, the dopant may be included in an amount of 0.1 wt% to 30 wt% based on 100 wt% of the host in the emission layer.

In the exemplary embodiment of the present specification, the host material of the light emitting layer includes a condensed aromatic ring derivative and a hetero ring-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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

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

When the emission layer emits red light, the emission dopants include PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium). ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum), but is not limited thereto. When the emission layer emits green light, the emission dopant is a phosphor such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium), or Alq3(tris(8-hydroxyquinolino)aluminum), anthracene compound, pyrene type A fluorescent material such as a compound or a boron-based compound may be used, but is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant is a phosphorescent material such as (4,6-F ₂ ppy) ₂ Irpic, but spiro-DPVBi, spiro-6P, distillbenzene (DSB), distrylarylene (DSA ), a PFO-based polymer, a PPV-based polymer, an anthracene-based compound, a pyrene-based compound, a boron-based compound, or the like may be used, but is not limited thereto.

The hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer, and the hole injection material is a material capable of receiving holes from the anode at a low voltage, and is a high occupied HOMO (highest occupied material) of the hole injection material. It is preferable that molecular orbital) is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, etc., but are not limited thereto. The thickness of the hole injection layer may be 1 nm to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing deterioration of the hole injection characteristics, and when the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There is an advantage that can prevent it.

The hole transport layer may serve to facilitate transport of holes. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

The hole control layer may be provided between the hole transport layer and the light emitting layer, and serves to effectively receive holes from the hole transport layer and control the amount of holes transferred to the light emitting layer by adjusting hole mobility. In addition, the electrons supplied from the light emitting layer can simultaneously perform the role of an electron barrier to prevent passing to the hole transport layer. Through this, it is possible to maximize the balance of holes and electrons in the emission layer to increase luminous efficiency, and improve stability and lifespan. Materials known in the art may be used as the material for the hole control layer.

The electron control layer may be provided between the light emitting layer and the electron transport layer, and serves to control the amount of electrons transferred to the light emitting layer by effectively receiving electrons from the electron transport layer and controlling electron mobility. In addition, it can simultaneously serve as a hole barrier preventing holes supplied from the emission layer from passing over to the electron transport layer. Through this, it is possible to maximize the balance of holes and electrons in the emission layer to increase luminous efficiency, and improve stability and lifespan. Materials known in the art may be used as a material for the electron control layer in addition to the compound.

The electron transport layer may serve to facilitate transport of electrons. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is suitable. Specific examples other than the above compounds include Al complexes of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.

In the exemplary embodiment of the present specification, the electron transport layer may further include an organometallic complex, and the organometallic complex may be mixed with the compound to be included in one layer. Specifically, the compound and the organic metal complex may be mixed and then vacuum-deposited, or a mixed layer may be formed by depositing each. In this case, there are effects such as controlling the energy level between the cathode or the electron injection layer and improving the bonding ability at the interface between the organic material and the metal. As the organometallic complex, at least one selected from LiQ, NaQ, LiF, CsF, BaF, BaO, and Al ₂ O ₃ may be used, but is not limited thereto.

The thickness of the electron transport layer may be 1 nm to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing deterioration of the electron transport characteristics, and if the thickness of the electron transport layer is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in the driving voltage to improve the movement of electrons. There is an advantage to be able to.

The electron injection layer may serve to facilitate injection of electrons. 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 the movement of excitons generated in the light emitting layer to the hole injection layer, and , A compound having excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

A capping layer may be provided on the cathode. Materials known in the art, such as a carbazole-based compound, may be used for the capping layer.

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

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

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

< Manufacturing example >

Manufacturing example 1. Synthesis of Intermediates A1 to A5

SM1 (hydrazine compound; 1 eq), SM2 (triethyl orthoester; 1.1 eq) and ammonium chloride (3.5 eq) were added to an excess of ethanol and heated to reflux according to the combination shown in Table 1 below. After 10 hours, the reaction was terminated, the temperature was stabilized at room temperature, and distilled under reduced pressure. Thereafter, the slurry was stirred through hexane and diethylether, filtered, and purified through column chromatography with hexane to prepare intermediates A1 to A5 of Table 1 below.

Manufacturing example 2. Synthesis of Intermediates B1 and B2

SM1 (1-benzoyl-2-formylhydrazine compound; 1 eq) described in Table 2 below was added to an excess of toluene, followed by addition of Lawesson's reagent (1.1 eq), followed by heating to reflux. After 3 hours, the reaction was terminated and the temperature was stabilized at room temperature, followed by distillation under reduced pressure. After that, it was purified through column chromatography with hexane and solidified with ethanol to prepare intermediates B1 and B2 of Table 2 below.

Manufacturing example 3. Synthesis of intermediates C1 to C7

After adding SM1 (1eq) shown in Table 3 to an excess amount of tetrahydrofuran (THF) and stabilizing the temperature at -78°C while stirring, n-butyllithium (n-BuLi; hexane solution, 2.5M, 1.3eq ) Was added and stirred for 1 hour, and then bromine (1.3eq) was added dropwise. After 1 hour, the reaction was terminated, the temperature was stabilized at 0° C., titrated with 1N hydrogen chloride, and extracted with ethyl acetate and sodium thiosulfate aqueous solution. Then, it was recrystallized with diethylether to prepare intermediates C1 to C7 of Table 3 below.

Manufacturing example 4. Synthesis of Intermediates T1 to T17

In the combination described in Table 4 below, SM1 (1eq) and SM2 (1.3eq) were added to 1,4-dioxane (12 times compared to SM1 based on the mass ratio), and potassium acetate (3eq) was added, followed by stirring and refluxing. Palladium acetate (0.02eq) and tricyclohexylphosphine (0.04eq) were stirred in 1,4-dioxane for 5 minutes and then added. After 2 hours, the reaction was confirmed and cooled to room temperature. After adding ethanol and water, filtering was performed and recrystallized with ethyl acetate to prepare intermediates T1 to T17 shown in Table 4 below.

Manufacturing example 5. Synthesis of intermediates S1 to S15

In Preparation Example 4, the intermediates S1 to S15 of Table 5 were prepared in the same manner as in Preparation Example 4, except that the combination of SM1 and SM2 was used as shown in Table 5 below.

Manufacturing example 6. Synthesis of intermediates Z1 to Z19

After adding SM1 (1eq) and SM2 (1.02eq) to an excess amount of tetrahydrofuran (THF) in the combination described in Table 6 below, a 2M aqueous potassium carbonate solution (30 vol% of THF) was added, and tetrakistriphenyl- Phosphinopalladium (2mol%) was added, followed by heating and stirring for 10 hours. After the temperature was lowered to room temperature and the reaction was terminated, the aqueous potassium carbonate solution was removed to separate the layers. After removing the solvent, distillation under vacuum and recrystallization from tetrahydrofuran and ethyl acetate were performed to prepare intermediates Z1 to Z19 of Table 6 below.

Manufacturing example 7. Synthesis of compounds 1 to 19

After adding SM1 (1eq) and SM2 (1.02eq) to an excess of 1,4-dioxane in the combination shown in Table 7 below, 2M potassium carbonate aqueous solution (30 vol% compared to THF) was added, and palladium acetate (0.02eq ) And tricyclohexylphosphine (0.04eq) were stirred in 1,4-dioxane for 5 minutes and then added, followed by heating and stirring for 10 hours. After the temperature was lowered to room temperature and the reaction was terminated, the aqueous potassium carbonate solution was removed to separate the layers. After removal of the solvent, distillation under vacuum and recrystallization with tetrahydrofuran and ethyl acetate were performed to prepare compounds 1 to 19 of Table 7 below.

Compounds 20 to 24 were prepared in the same manner as in the preparation method of Compounds 1 to 19.

Compound 20 Compound 21 Compound 22

Compound 23 compound 24

Example 1.

A substrate on which ITO/Ag/ITO was deposited to a thickness of 70 Å/1,000 Å/70 Å as an anode was cut into a size of 50 mm×50 mm×0.5 mm, placed in distilled water containing a dispersant, and washed with ultrasonic waves. The detergent was manufactured by Fischer Co., and the distilled water was Millipore Co. Distilled water filtered twice with the product's filter was used. After washing the anode for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the prepared anode, the following HI-1 was thermally vacuum-deposited to a thickness of 50 Å to form a hole injection layer, and the following HT1, a material for transporting holes, was vacuum-deposited to a thickness of 1,150 Å to form a hole transport layer. Then, a hole control layer was formed using the following HT2 (150Å), and the following BH1 as a host and the following BD1 (2% by weight) as a dopant were vacuum-deposited to a thickness of 360Å to form a light emitting layer. Thereafter, ETM1 was deposited to a thickness of 50 Å to form an electron control layer, and Compound 1 prepared in Preparation Example 7 and the following Liq were mixed at a mass ratio of 7:3 to form an electron transport layer having a thickness of 250 Å. After sequentially forming a 50Å-thick magnesium and lithium fluoride (LiF) as an electron injection layer, and forming a negative electrode to be 200Å in a thickness ratio of 1:4 magnesium and silver, the following CP1 was used as the CPL (Capping layer) of the negative electrode. The device was completed by depositing to a thickness of 600Å. In the above process, the deposition rate of the organic material was maintained at 1 Å/sec.

Compound 20 Compound 21 Compound 22

Compound 23 compound 24

Examples 2 to 29.

The organic light emitting devices of Examples 2 to 29 were prepared in the same manner as in Example 1, except that the compounds shown in Table 8 below were used instead of ETM1 and Compound 1 when forming the electron controlling layer and the electron transport layer in Example 1, respectively. I did. In the case of Example 17, the electron control layer was not formed.

Comparative Examples 1 to 5

Organic light emitting devices of Comparative Examples 1 to 5 were prepared in the same manner as in Example 1, except that the compounds shown in Table 8 below were used instead of ETM1 and Compound 1, respectively, when forming the electron controlling layer and the electron transport layer in Example 1 I did. In the case of Comparative Example 1, the electron control layer was not formed.

For the organic light emitting devices of the above Examples and Comparative Examples, the results of measuring the performance such as voltage, luminous efficiency, color coordinates, and lifetime at a current density of 20 mA/cm ² are shown in Table 8 below. T95 is a measure of the time when the luminance becomes 95% of the initial luminance.

Experimental example
20 mA/㎠ Electronic control layer Electron transport layer Voltage(V)
(@20mA/cm ² ) Cd/A
(@20mA/cm ² ) Color coordinates
(x,y) life span
(T95, h)
(@20mA/cm ² ) Example 1 ETM1 Compound 1 3.49 7.12 (0.135, 0.138) 53.5 Example 2 ETM1 Compound 2 3.48 7.23 (0.134, 0.137) 52.1 Example 3 ETM1 Compound 3 3.52 6.85 (0.133, 0.139) 47.8 Example 4 ETM1 Compound 4 3.43 7.15 (0.135, 0.138) 55.8 Example 5 ETM1 Compound 5 3.50 7.20 (0.134, 0.138) 49.1 Example 6 ETM1 Compound 6 3.44 7.11 (0.136, 0.139) 49.0 Example 7 ETM1 Compound 9 3.62 6.89 (0.133, 0.139) 46.5 Example 8 ETM1 Compound 10 3.58 6.87 (0.135, 0.138) 47.4 Example 9 ETM1 Compound 11 3.60 6.88 (0.134, 0.138) 47.0 Example 10 ETM1 Compound 13 3.49 7.21 (0.136, 0.139) 51.3 Example 11 ETM1 Compound 14 3.48 7.08 (0.136, 0.139) 55.1 Example 12 ETM1 Compound 15 3.60 6.79 (0.135, 0.138) 47.3 Example 13 ETM1 Compound 16 3.61 6.89 (0.135, 0.138) 47.4 Example 14 ETM1 Compound 17 3.48 7.18 (0.134, 0.138) 50.9 Example 15 ETM1 Compound 18 3.44 7.14 (0.136, 0.139) 51.0 Example 16 ETM1 Compound 19 3.55 6.84 (0.135, 0.138) 47.1 Example 17 - Compound 9 3.47 7.19 (0.133, 0.139) 46.5 Example 18 Compound 7 ETM2 3.63 6.87 (0.135, 0.138) 46.9 Example 19 Compound 8 ETM2 3.71 6.86 (0.134, 0.138) 47.1 Example 20 Compound 12 ETM2 3.50 7.01 (0.135, 0.138) 55.8 Example 21 Compound 7 Compound 14 3.58 7.23 (0.134, 0.137) 51.0 Example 22 Compound 12 Compound 19 3.59 7.16 (0.135, 0.138) 53.4 Example 23 ETM1 Compound 20 3.40 7.09 (0.135, 0.138) 50.8 Example 24 ETM1 Compound 21 3.48 7.23 (0.134, 0.138) 53.4 Example 25 ETM1 Compound 22 3.47 7.21 (0.135, 0.138) 51.4 Example 26 ETM1 Compound 23 3.44 7.19 (0.134, 0.138) 52.0 Example 27 ETM1 Compound 24 3.42 7.12 (0.135, 0.138) 53.8 Example 28 Compound 22 ETM2 3.48 7.12 (0.135, 0.138) 54.1 Example 29 Compound 2 Compound 22 3.43 7.28 (0.135, 0.138) 59.1 Comparative Example 1 - ET1 4.23 4.23 (0.133, 0.139) 30.8 Comparative Example 2 ETM1 ET1 3.91 6.23 (0.135, 0.138) 40.1 Comparative Example 3 ETM1 ET1 3.98 6.33 (0.134, 0.138) 38.4 Comparative Example 4 ETM1 ET2 3.88 6.08 (0.133, 0.139) 39.5 Comparative Example 5 ETM1 ET3 4.02 6.41 (0.133, 0.139) 41.2

From the results of Table 8, it can be seen that when the compound according to an exemplary embodiment of the present specification is included in the electron control layer and/or the electron transport layer, luminous efficiency and lifespan are improved compared to the case where it is not.

Specifically, not only Comparative Examples 4 and 5 using ET2 and ET3 containing only one azine ring, as well as Comparative Examples 1 to 5 using ET1, which is a phenyl group in which X1 to X6 are all N and Ar1 to Ar4 are all unsubstituted in Formula 1 herein. It can be seen that the luminous efficiency and lifetime characteristics of 3 appear much lower than in the Example using the compound according to Formula 1 herein.

1: first electrode
2: hole injection layer
3: hole transport layer
4: hole control layer
5: light emitting layer
6: electronic control layer
7: electron transport layer
8: electron injection layer
9: second electrode

Claims (12)

Compound represented by the following formula (1):
[Formula 1]

In Formula 1,
Y1 is O or S,
X1 to X6 are each independently N or CR,
At least one of X1 to X3; And at least one of X4 to X6 is necessarily N,
L1 to L4 are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar1 to Ar4 are each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
At least three of Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
When all of X1 to X6 are N and all of Ar1 to Ar4 are phenyl groups, at least one of Ar1 to Ar4 is deuterium; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted cycloalkyl group; And a phenyl group substituted with one or more substituents selected from a substituted or unsubstituted alkyl group,
R, R1 and R2 are each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxyl group; Halogen group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; Or a substituted or unsubstituted arylthio group,
a and b are each independently an integer of 1 to 4,
When a or b is each of 2 or more, the substituents in the 2 or more parentheses are the same as or different from each other. The method according to claim 1,
Formula 1 is a compound represented by any one of the following Formulas 1-1 to 1-6:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-1 to 1-6,
Y1, X1 to X6, L1 to L4, Ar1 to Ar4, R1, R2, a and b are the same as defined in Formula 1 above. The method according to claim 1,
Formula 1 is a compound represented by any one of the following structural formulas:

In the above structural formula,
Y1, L1 to L4, Ar1 to Ar4, R1, R2, a and b are the same as defined in Formula 1 above. The method according to claim 1,
The compounds Ar1 to Ar4 are each independently represented by any one of the following structural formulas:

In the above structural formula,
Q1 is NRa, CRbRc, O or S,
R3 and R4 are each independently hydrogen; heavy hydrogen; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted cycloalkyl group,
Ra to Rc are each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, and Rb and Rc may be bonded to each other to form a ring,
d4 is an integer from 0 to 4,
d5 is an integer from 0 to 5,
d7 is an integer from 0 to 7,
d9 is an integer from 0 to 9,
e is 1 or 2,
When d4, d5, d7, d9 and e are each 2 or more, the substituents in the two or more parentheses are the same as or different from each other,
* Is a position connected to Formula 1 above. The method according to claim 1,
The L1 to L4 are each independently a direct bond; Or a compound that is an arylene group having 6 to 30 carbon atoms. The method according to claim 1,
R1 and R2 are each independently hydrogen; heavy hydrogen; Nitrile group; An alkyl group having 1 to 50 carbon atoms; Or a compound that is an aryl group having 6 to 30 carbon atoms. The method according to claim 1,
The compound represented by Formula 1 is any one selected from the following structural formulas:

. A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 7 device. The method of claim 8,
The organic material layer includes one or more electron transport layers, and at least one of the electron transport layers includes the compound. The method of claim 9,
An organic light-emitting device wherein the electron transport layer comprising the compound further comprises an organic metal complex. The method of claim 8,
The organic material layer includes one or more electron controlling layers, and at least one of the electron controlling layers includes the compound. The method of claim 8,
The organic material layer includes an electron transport layer and an electron control layer, and the electron transport layer and the electron control layer contain the compound.

Images