KR20200026752A - Organic light emitting device - Google Patents

Abstract

The present specification relates to an organic light emitting device comprising: a first electrode; a second electrode installed to face the first electrode; and a first organic layer and a second organic layer installed between the first electrode and the second electrode, wherein the first organic layer comprises a compound represented by chemical formula 1 and the second organic layer comprises a compound represented by chemical formula 3.

Description

Organic light emitting element {ORGANIC LIGHT EMITTING DEVICE}

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0104684 filed with the Korea Intellectual Property Office on September 3, 2018, the entire contents of which are incorporated herein.

The present specification relates to an organic light emitting device.

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

Conventionally, aromatic diamine derivatives and aromatic condensed ring diamine derivatives have been known as hole transport materials used in organic EL devices. However, in this case, since the applied voltage is mostly high, problems such as deterioration of device life and large power consumption have arisen. As a solution of the above problem, a method of doping an electron-accepting compound such as Lewis acid or using a hole injection layer of an organic EL device has been proposed. However, the above method has shown that there is a limitation in the hole injection and transport, and therefore, the effect of low voltage, high efficiency, and long life time can be achieved by the combination of the material between the hole transport layer or the hole control layer or the material of the hole transport layer and the multilayer hole control layer. I tried to draw. In general, the hole transport layer aromatics were substituted tertiary amines, and the device characteristics found in the combination group of the materials have shown various results. Therefore, there is a continuous demand for the development of new materials for improving device characteristics due to hole transport and carrier control.

United States Patent Application Publication No. 2004-0251816

The present specification is to provide an organic light emitting device.

Herein is a first electrode; A second electrode provided to face the first electrode; And a first organic material layer and a second organic material layer provided between the first electrode and the second electrode.

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

The second organic material layer is an organic light emitting device comprising a compound represented by the following formula (3):

 [Formula 1]

In Chemical Formula 1,

X is O or S,

R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

At least one of R1 to R4 is represented by the formula (2A) or 2B,

n1 to n4 are each independently an integer of 1 to 4,

when n1 to n4 are each independently 2 or more, the substituents in parentheses are the same as or different from each other,

[Formula 2A]

[Formula 2B]

In Chemical Formulas 2A and 2B,

At least one of A1 to A3 is N, and the other is CH or combines with an adjacent group of L1, L2, L3, Ar4 and Ar5 to form a substituted or unsubstituted ring,

L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted ring,

Ar4 and Ar5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted ring,

Ar6 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, a is an integer from 0 to 5,

[Formula 3]

In Chemical Formula 3,

X 1 is N or CH,

Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

The organic light emitting device using the compound according to the exemplary embodiment of the present specification in the hole blocking layer, the electron control layer, the electron transport layer, or the electron injection and transport layer, respectively, can have a low driving voltage, high luminous efficiency, or long life.

1, 3, and 4 show an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
FIG. 2 shows a substrate 1, an anode 2, a hole transport layer 5, a light emitting layer 3, a hole blocking layer or an electron control layer 6, the electron injection and transport layer 7 and the cathode 4 are sequentially stacked An example of the organic light emitting element is shown.

Hereinafter, this specification is demonstrated in detail.

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

In the present specification, when a part "includes" a certain component, this means that the component may further include other components, except for the case where there is no description to the contrary.

Herein is a first electrode; A second electrode provided to face the first electrode; And a first organic material layer and a second organic material layer provided between the first electrode and the second electrode, wherein the first organic material layer includes a compound represented by Chemical Formula 1, and the second organic material layer is represented by Chemical Formula 3 It provides an organic light emitting device comprising the compound represented.

According to the exemplary embodiment of the present specification, the compound represented by Chemical Formula 1 has an advantage of controlling triplet energy by having the core structure as described above, and may exhibit long life and high efficiency.

According to an exemplary embodiment of the present specification, since the compound represented by the formula (1) has a lower absolute value of the LUMO energy level than the compound represented by the formula (3) to enable smooth electron transfer to the light emitting layer, the formulas (1) and (3) An organic light-emitting device comprising has an excellent effect in efficiency and / or life.

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

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

As used herein, the term "substituted or unsubstituted" is hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" 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 linked.

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 chain, carbon number is not particularly limited, but is preferably 1 to 60. 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-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

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

In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. 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 and the like It may be, but is not limited to such.

In the present specification, the alkenyl group may be linear or branched chain, carbon number 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, styrenyl group and the like, but are not limited thereto.

In the present specification, the amine group is selected from the group consisting of -NH ₂ , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group. Although it may be selected, the carbon number is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group. , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthre And a nilfluorenylamine group, an N-biphenyl fluorenylamine group and the like, but is not limited thereto.

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

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-60. Specifically, the polycyclic aryl group may be naphthyl group, anthracene group, phenanthrene group, pyrene group, perylene group, chrysene group, fluorene group and the like, but is not limited thereto.

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

등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorene group is substituted,

Etc., but is not limited thereto.

In the present specification, the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number of a heterocyclic group is not specifically limited, It is preferable that it is C2-C60. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group , Pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanththroline group, isoxazole group, thiaxazole group Diazole group, dibenzofuran group, dibenzosilol group, phenoxathiine, phenoxazine group, phenoxazine group, phenothiazine group, dihydroindenocarbazole group, spirofluorene xanthene group and spirofluorene Thioxanthene groups, etc., but are not limited thereto. Is not. Etc., but is not limited thereto. In the present specification, in a substituted or unsubstituted ring in which adjacent groups are bonded to each other, a “ring” means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.

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

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

In the present specification, the divalent or trivalent aryl group may be monocyclic or polycyclic, and means that the aryl group has two or three bonding positions, that is, a divalent or trivalent group. The description of the aforementioned aryl groups can be applied except that they are each divalent or trivalent.

In the present specification, the arylene group refers to a divalent group having two bonding positions in the aryl group. The description of the aforementioned aryl groups can be applied except that they are each divalent.

In the present specification, the divalent heterocyclic group refers to a divalent group having two bonding positions in the heterocyclic group. The description of the aforementioned heterocyclic groups can be applied except that they are each divalent.

According to an exemplary embodiment of the present specification, the R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, the R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

According to an exemplary embodiment of the present specification, the R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

According to an exemplary embodiment of the present specification, the R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, the R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, a group other than the general formula 2A or 2B of the R1 to R4 is hydrogen or deuterium.

According to an exemplary embodiment of the present specification, at least one of the groups R1 to R4 other than the general formula 2A or 2B is an alkyl group, an aryl group, or an aryl group substituted with an alkyl group, the rest is hydrogen or deuterium.

According to an exemplary embodiment of the present specification, at least one of the groups other than the formula 2A or 2B of the R1 to R4 is a methyl group; n-butyl group; tert-butyl group; A phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group; Naphthyl group; Or a fluorene group substituted with a methyl group, and the remainder is hydrogen or deuterium.

According to an exemplary embodiment of the present specification, n1 is 2, and the adjacent R1 combines with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, n1 is 2, and the adjacent R1 combine with each other to form a substituted or unsubstituted hydrocarbon ring.

According to an exemplary embodiment of the present specification, n1 is 2, and the adjacent R1 combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to an exemplary embodiment of the present disclosure, wherein n1 is 2, the adjacent R1 is bonded to each other to form a substituted or unsubstituted benzene ring.

According to an exemplary embodiment of the present disclosure, the n1 is 2, the adjacent R1 is bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present disclosure, wherein n2 is 2, the adjacent R2 combines with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, n2 is 2 and the adjacent R2 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

According to an exemplary embodiment of the present disclosure, wherein n2 is 2, the adjacent R2 combines with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, n2 is 2, and the adjacent R2 are bonded to each other to form a substituted or unsubstituted benzene ring.

According to an exemplary embodiment of the present specification, n2 is 2, and the adjacent R2 are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, the n1 is 2, the adjacent R1 is bonded to each other to form a substituted or unsubstituted ring, the n2 is 2, the adjacent R2 is bonded to each other to form a benzene ring. .

According to an exemplary embodiment of the present specification, at least one of the R1 to R4 is represented by the formula 2A or 2B.

[Formula 2A]

[Formula 2B]

In Formulas 2A and 2B, the definitions of L1 to L3, Ar4 to Ar6, A1 to A3 and a are as described above.

According to an exemplary embodiment of the present specification, one of the R1 to R4 is represented by the formula 2A or 2B.

According to an exemplary embodiment of the present specification, two of the R1 to R4 are represented by the formula 2A or 2B.

According to an exemplary embodiment of the present specification, one of the R2 and one of the R3 is represented by the formula 2A or 2B.

According to an exemplary embodiment of the present disclosure, at least one of A1 to A3 is N, the remainder is CH, or combine with adjacent groups of L1, L2, L3, Ar4 and Ar5 to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, the L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, the L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, the L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, the L1 to L3 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a biphenylylene group.

According to an exemplary embodiment of the present specification, L3 is a direct bond; Phenylene group; Biphenylylene group; Naphthylene group; Divalent thiophene group; Divalent furan group; Divalent dibenzothiophene group; Divalent dibenzofuran group; Divalent carbazole groups unsubstituted or substituted with an aryl group or an alkylaryl group; Divalent benzocarbazole groups unsubstituted or substituted with an aryl group or an alkylaryl group; Divalent dibenzosilol groups substituted or substituted with alkyl groups; Divalent phenoxathiine group; Divalent phenoxazine; Divalent phenothiazine group; Divalent pyridine group; A divalent dihydroindenocarbazole group unsubstituted or substituted with an alkyl group; Divalent groups in which dibenzothiophene and a phenyl group are linked; Or a divalent group linked to a carbazole and a phenyl group.

According to an exemplary embodiment of the present specification, L3 is a direct bond; Phenylene group; Biphenylylene group; Naphthylene group; Divalent thiophene group; Divalent furan group; Divalent dibenzothiophene group; Divalent dibenzofuran group; Divalent carbazole groups unsubstituted or substituted with a phenyl group or a methylphenyl group; Divalent benzocarbazole groups unsubstituted or substituted with a phenyl group or a methylphenyl group; Divalent dibenzosilol group substituted or substituted with a methyl group; Divalent phenoxathiine group; Divalent phenoxazine; Divalent phenothiazine group; Divalent pyridine group; A divalent dihydroindenocarbazole group unsubstituted or substituted with a methyl group; Divalent groups in which dibenzothiophene and a phenyl group are linked; Or a divalent group linked to a carbazole and a phenyl group.

According to an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group of A1 to A3 to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted benzene ring.

According to an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted benzene ring.

According to an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted benzene ring.

According to an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and each independently CN, alkyl group, alkoxy group, haloalkyl group, haloalkoxy group, alkylsilyl group, aryl group, alkylaryl group or heterocyclic ring An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with a group; Or a heterocyclic group having 2 to 15 carbon atoms which is unsubstituted or substituted with a CN, an alkyl group, an alkoxy group, a haloalkyl group, a haloalkoxy group, an alkylsilyl group, an aryl group or a heterocyclic group, or is bonded to an adjacent group of A1 to A3 to benzene To form a ring.

According to an exemplary embodiment of the present specification, Ar4 and Ar5 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 fluorene group, a triphenylene group, a phenanthrene group, a fluoranthene group, Phenylene group, carbazole group, benzocarbazole group, dibenzofuran group, dibenzothiophene group, dibenzosilol group, phenoxathiine group, phenoxazine group, phenoxazine group, phenothiazine group, pyridyl group, Dihydroindenocarbazole, an arylsilyl group, an alkylsilyl group, a spirofluorene xanthene group and a group in which one or two or more groups selected from spirofluorene thioxanthene groups are bonded, and these are CN, an alkyl group, an alkoxy group and a haloalkyl group. It may be substituted with a haloalkoxy group, an alkylsilyl group, an aryl group, an alkylaryl group or a heterocyclic group. Wherein the heterocyclic group as a substituent is a carbazole group, a benzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilol group, a phenoxathiine, a phenoxazine group, a phenothiazine group, It may be a pyridyl group or a dihydroindenocarbazole group, and the aryl group as a substituent may be a phenyl group, a biphenyl group, a naphthyl group, or a triphenylene group. In addition, the alkyl group may be a methyl group, or tert-butyl group, the alkoxy group may be a methoxy group, the haloalkyl group may be a trifluoromethyl group, the haloalkoxy group may be a trifluoromethoxy group, the alkyl The silyl group may be a methylsilyl group.

According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formula 1-1 to Formula 1-5.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Chemical Formulas 1-1 to 1-5,

The definitions of X, R1 to R4, L1 to L3, A1 to A3, Ar4, Ar5 and n1 to n4 are as defined above, and L1 ', L2', L3 ', A1', A2 ', A3', Ar4 'and Ar5 'is the same as the definition of L1, L2, L3, A1, A2, A3, Ar4 and Ar5, respectively.

According to an exemplary embodiment of the present specification, two of A1 to A3 of Formula 2A are N.

According to an exemplary embodiment of the present specification, A1 to A3 of Formula 2A are N.

According to an exemplary embodiment of the present specification, Formula 2A may be selected from the following structural formulas.

In the above structural formula, the definitions of L1 to L3, Ar4 and Ar5 are as described above.

According to an exemplary embodiment of the present specification, Ar6 of the formula 2B is hydrogen.

According to an exemplary embodiment of the present specification, X1 is CH.

According to an exemplary embodiment of the present specification, X1 is N.

According to an 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; Or a substituted or unsubstituted heteroring group.

According to an 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 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an 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 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an 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 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 15 carbon atoms unsubstituted or substituted with an aryl group having 6 to 15 carbon atoms. to be.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 15 carbon atoms; Biphenyl group; Naphthyl group; Anthracene groups; Phenanthrene group; Or pyrene group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a tert-butyl group or a phenyl group unsubstituted or substituted with a phenyl group; Biphenyl group; Naphthyl group; Anthracene groups; Or phenanthrene group.

According to an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 is unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heterocyclic ring having 2 to 20 carbon atoms. It is an aryl group having 6 to 20 carbon atoms substituted with at least one selected from the group consisting of a heterocyclic group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 is unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heterocyclic ring having 2 to 20 carbon atoms. A phenyl group substituted with at least one selected from the group consisting of heterocyclic groups having 2 to 20 carbon atoms; A biphenyl group substituted with one or more selected from the group consisting of an aryl group having 6 to 20 carbon atoms and a heterocyclic group having 2 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; Or a terphenyl group substituted with at least one selected from the group consisting of an aryl group having 6 to 20 carbon atoms and a heterocyclic group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 is a pyridine group unsubstituted or substituted with a methyl group or a phenyl group, a dibenzothiophene group, a pyrimidine group, a pyrazine group, a quinoline group, a phenanthrol unsubstituted or substituted with a pyridine group A phenyl group substituted with at least one selected from the group consisting of a thiophene group, a phenanthrene group, a pyrene group, a biphenyl group, a naphthyl group, and an anthracene group, unsubstituted or substituted with a lean group, a benzothiophene group and a thiophene group; A pyridine group unsubstituted or substituted with a methyl group, a pyrimidine group substituted or unsubstituted with a methyl group, a pyrazine group, a benzothiophene group, a dibenzothiophene group, a phenyl group, a naphthyl group, a phenanthrene group, an anthracene group, and pyrene A biphenyl group substituted with one or more selected from the group consisting of groups; Or a terphenyl group substituted with at least one selected from the group consisting of a pyridine group and a phenanthrene group.

According to an exemplary embodiment of the present specification, Chemical Formula 3 may be represented by the following Chemical Formula 3-1.

[Formula 3-1]

In Chemical Formula 3-1,

X1 'is N or CH,

Ar1 'and Ar2' are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group,

L is a direct bond; Or a substituted or unsubstituted divalent or trivalent aryl group,

Ar3 'is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n5 is 1 or 2, and when n5 is 2, the substituents in parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, X1 'is CH.

According to an exemplary embodiment of the present specification, X1 'is N.

According to an 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; Or a substituted or unsubstituted heteroring group.

According to an 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 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an 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 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an 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 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 'and Ar2' are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 'and Ar2' are the same as or different from each other, and each independently having 6 to 15 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 15 carbon atoms It is an aryl group.

According to an exemplary embodiment of the present specification, Ar1 'and Ar2' are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 15 carbon atoms; Biphenyl group; Naphthyl group; Anthracene groups; Phenanthrene group; Or pyrene group.

According to an exemplary embodiment of the present specification, Ar1 'and Ar2' are the same as or different from each other, and each independently a tert-butyl group or a phenyl group unsubstituted or substituted with a phenyl group; Biphenyl group; Naphthyl group; Anthracene groups; Or phenanthrene group.

According to an exemplary embodiment of the present specification, L is a direct bond.

According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted divalent aryl group having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted divalent aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted divalent aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L is a divalent aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L is a phenylene group.

According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted trivalent aryl group having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted trivalent aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted trivalent aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L is a trivalent phenyl group; Trivalent biphenyl group; Or a trivalent terphenyl group.

According to an exemplary embodiment of the present specification, n5 is 1.

According to an exemplary embodiment of the present specification, n5 is 2, when n5 is 2, two or more Ar3 'are the same as or different from each other.

According to an exemplary embodiment of the present specification, Ar3 'is an aryl group having 6 to 60 carbon atoms; Or a C2-C60 heterocyclic group unsubstituted or substituted with a C1-C60 alkyl group, a C6-C60 aryl group, or a C2-C60 heterocyclic group.

According to an exemplary embodiment of the present specification, Ar3 'is an aryl group having 6 to 30 carbon atoms; Or a C 2-30 heterocyclic group unsubstituted or substituted with an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 'is an aryl group having 6 to 20 carbon atoms; Or a C 2-20 heterocyclic group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heterocyclic group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 'is a pyridine group unsubstituted or substituted with a methyl group or a phenyl group; Dibenzothiophene group unsubstituted or substituted with a pyridine group; Pyrimidine groups; Pyrazine groups; Quinoline groups; Phenanthrosine group; Benzothiophene group; A thiophene group unsubstituted or substituted with a thiophene group; Phenanthrene group; Pyrene group; Phenyl group; Biphenyl group; Naphthyl group; Or an anthracene group.

According to an exemplary embodiment of the present specification, Chemical Formula 3 is represented by any one of the following Chemical Formulas 3-2 to 3-5.

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

[Formula 3-5]

In Formulas 3-2 to 3-5, Ar1 and Ar2 have the same definitions as in Formula 3, at least one of Ar31 and Ar32, at least one of Ar34 and Ar35, and at least one of Ar36 and Ar37 are substituted or unsubstituted. Heterocyclic group; Or an aryl group substituted with a heterocyclic group, the remainder is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, Ar33 is a substituted or unsubstituted heterocyclic group; Or an aryl group substituted with a heterocyclic group.

According to an exemplary embodiment, at least one of Ar31 and Ar32, at least one of Ar34 and Ar35, and at least one of Ar36 and Ar37 may be a pyridine group unsubstituted or substituted with a methyl group or a phenyl group; Dibenzothiophene group unsubstituted or substituted with a pyridine group; Pyrimidine groups; Pyrazine groups; Quinoline groups; Phenanthrosine group; Benzothiophene group; Or a thiophene group unsubstituted or substituted with a thiophene group.

According to an exemplary embodiment, Ar33 is a pyridine group; Or a pyrimidine group.

In addition, according to an exemplary embodiment of the present specification, Chemical Formula 1 is selected from the following structural formulas.

In addition, according to an exemplary embodiment of the present specification, Chemical Formula 3 is selected from the following structural formulas.

The first and second organic material layers of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layered structure in which two or more organic material layers are stacked. For example, the first organic material layer of the present specification may be composed of 1 to 3 layers. In addition, the organic light emitting device of the present specification may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, or the like as an organic material layer, or a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron injection and a transport layer. have. However, the structure of the organic light emitting device is not limited thereto, and may include more or fewer organic layers.

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

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

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

In addition, the organic light emitting device may further include an electron charge generating layer.

According to an exemplary embodiment of the present specification, the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And at least two light emitting layers provided between the first electrode and the second electrode. Two or more first and second organic material layers provided between the two or more light emitting layers and the first electrode or between the two or more light emitting layers and the second electrode, wherein the two or more first and second organic material layers Each includes a compound represented by Chemical Formula 1 or a compound represented by Chemical Formula 3.

According to the exemplary embodiment of the present specification, the first organic material layer includes a hole blocking layer or an electron control layer, the second organic material layer includes an electron transport layer, and the hole blocking layer or the electron control layer is represented by Chemical Formula 1 To include a compound, the electron transport layer may include a compound represented by the formula (3).

According to the exemplary embodiment of the present specification, the first organic material layer includes a hole blocking layer or an electron control layer, the second organic material layer includes an electron injection and transport layer, and the hole blocking layer or the electron control layer is represented by Chemical Formula 1 It includes a compound represented by, and the electron injection and transport layer may include a compound represented by the formula (3).

According to one embodiment of the present specification, the first and second organic material layers further include a hole injection layer or a hole transport layer including a compound including an arylamino group, a carbazole group, or a benzocarbazole group in addition to the organic material layer including the compound. .

In another exemplary embodiment, the organic light emitting diode may be an organic light emitting diode having a structure 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 organic light emitting device having an inverted type 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 specification is illustrated in FIGS. 1 to 4.

4 illustrates a structure of a general organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. Also, referring to FIGS. 1 and 3, the organic light emitting diode according to the exemplary embodiment of the present specification may include two or more light emitting layers. In addition, each light emitting layer may independently include a fluorescent dopant or a phosphorescent dopant. When the light emitting layer is two layers, one light emitting layer may include a fluorescent dopant, and the other light emitting dopant.

In example embodiments, the organic light emitting diode may include two or more light emitting layers emitting light of different wavelength bands between the first electrode and the second electrode.

In addition, according to the exemplary embodiment of the present specification, the two or more light emitting layers may be provided in the vertical direction of the direction of the second electrode from the first electrode, or may be provided in the horizontal direction.

2 shows a substrate 1, an anode 2, a hole transport layer 5, a light emitting layer 3, a hole blocking layer or an electron control layer 6, an electron injection and transport layer 7 and a cathode 4 sequentially. The structure of the stacked organic light emitting device is illustrated. Referring to FIG. 2, another organic light emitting diode according to an exemplary embodiment of the present specification may include three or more light emitting layers. In addition, another layer may be additionally provided between each light emitting layer and the light emitting layer. When the light emitting layer is provided with three or more layers, each light emitting layer may include a blue fluorescent light emitting layer. In addition, in the structure shown in FIG. 3, the compound represented by Chemical Formula 1 may be included in the hole blocking layer or the electron control layer 6, and the compound represented by Chemical Formula 3 may be included in the electron injection and transport layer 7.

In addition, according to the exemplary embodiment of the present specification, the light emitting layer of the three or more layers may be provided in a vertical direction of the direction of the second electrode from the first electrode, or may be provided in the horizontal direction. More specifically, the first electrode may be provided in a horizontal direction in the direction of the second electrode.

According to an exemplary embodiment of the present specification, the blue fluorescent light emitting layer includes a host and a dopant, and the host may be any one selected from the following structures.

The organic light emitting device of the present specification is a material and method known in the art, except that at least one layer of the first or second organic material layer includes a compound of the present specification, that is, the compounds represented by Chemical Formulas 1 and 3 above. Can be prepared.

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

 The organic light emitting device of the present specification is a material and method known in the art except that at least one layer of the first or second organic material layer includes the compound, that is, the compound represented by any one of Formulas 1 and 3 above. Can be prepared.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking first electrodes, first and second organic material layers, and second electrodes on a substrate. In this case, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. And an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above 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 compounds of Formulas 1 and 3 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

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

According to one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

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

As the anode material, a material having a large work function is generally preferred to facilitate hole injection. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection. 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; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes. The hole injection material has a hole injection effect at an anode, and has an excellent hole injection effect for a light emitting layer or a light emitting material. The compound which prevents the movement of the excited excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

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

The light emitting material is a material capable of emitting light in the visible region by receiving and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

The electron transporting material is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer.

The electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer. The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

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

The hole blocking layer is a layer that blocks the reaching of the cathode of the hole, and may be an electron control layer to control electrons reaching the light emitting layer. In addition, the electron charge generating layer is a layer for generating an electron charge.

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 according to a material used.

Fabrication of the organic light emitting device including the compound represented by Chemical Formulas 1 and 3 will be described in detail in the following Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

Preparation Example 1 Preparation of Compound EC1

The compound EC1-A (10 g, 26.6 mmol) and the compound EC1-B (12.3 g, 26.6 mmol) were completely dissolved in tetrahydrofuran (100 mL), followed by potassium carbonate (11.0 g, 79.7 mmol) in water 50 dissolved in mL and added. Tetrakistriphenyl-phosphinopalladium (0.92 g, 0.797 mmol) was added thereto, followed by heating and stirring for 8 hours. After the temperature was lowered to room temperature and the reaction was terminated, the white carbonate was filtered by removing the potassium carbonate solution. The filtered white solid was washed twice with tetrahydrofuran and ethyl acetate each to prepare compound EC1 (15.4 g, yield 81%).

MS [M + H] ⁺ = 716

Preparation Example 2 Preparation of Compound EC2

Except that each starting material was the same as the reaction scheme, the compound represented by the formula EC2 was prepared in the same manner as in the preparation method of EC1 of Preparation Example 1.

MS [M + H] ⁺ = 553

Preparation Example 3 Preparation of Compound EC3

Except that each starting material was the same as the reaction scheme, the compound represented by the formula EC3 was prepared in the same manner as the preparation method of EC1 of Preparation Example 1.

MS [M + H] ⁺ = 640

Preparation Example 4 Preparation of Compound EC4

Except that each starting material was the same as the reaction scheme, the compound represented by the formula EC4 was prepared by the same method as the preparation method of EC1 of Preparation Example 1.

MS [M + H] ⁺ = 640

Preparation Example 5 Preparation of Compound EC5

The compound EC5-A (10 g, 17.1 mmol) and the compound EC5-B (9.2 g, 34.2 mmol) were completely dissolved in tetrahydrofuran (100 mL), followed by potassium carbonate (7.1 g, 51.3 mmol) in water 50 dissolved in mL and added. Tetrakistriphenyl-phosphinopalladium (0.59 g, 0.513 mmol) was added thereto, followed by heating and stirring for 8 hours. After the temperature was lowered to room temperature and the reaction was terminated, the white carbonate was filtered by removing the potassium carbonate solution. The filtered white solid was washed twice with tetrahydrofuran and ethyl acetate to prepare compound EC5 (9.5 g, yield 70%).

MS [M + H] ⁺ = 795

Preparation Example 6 Preparation of Compound EC6

Except that each starting material was the same as the reaction scheme, a compound represented by the formula EC6 was prepared by the same method as the preparation method of EC1 of Preparation Example 1.

MS [M + H] ⁺ = 807

Preparation Example 7 Preparation of Compound EC7

A compound represented by Chemical Formula EC7 was prepared by the same method as the preparation method of EC1 of Preparation Example 1, except that each starting material was performed in the same manner as in the above scheme.

MS [M + H] ⁺ = 654

Preparation Example 8 Preparation of Compound EC8

Except that each starting material was the same as the reaction scheme, a compound represented by the formula EC8 was prepared in the same manner as in the preparation method of EC1 of Preparation Example 1.

MS [M + H] ⁺ = 821

Preparation Example 9 Preparation of Compound EC9

Except that each starting material was the same as the reaction scheme, the compound represented by the formula EC9 was prepared in the same manner as in the preparation method of EC1 of Preparation Example 1.

MS [M + H] ⁺ = 848

Preparation Example 10 Preparation of Compound EC10

A compound represented by Chemical Formula EC10 was prepared by the same method as the preparation method of EC1 of Preparation Example 1, except that each starting material was performed in the same manner as in the above scheme.

MS [M + H] ⁺ = 537

Preparation Example 11 Preparation of Compound ET1

Except that each starting material was the same as the reaction scheme, a compound represented by the formula ET1 was prepared by the same method as the preparation method of EC1 of Preparation Example 1.

MS [M + H] ⁺ = 757

Preparation Example 12 Preparation of Compound ET2

Except that each starting material was the same as the reaction scheme, a compound represented by the formula ET2 was prepared by the same method as the preparation method of EC1 of Preparation Example 1.

MS [M + H] ⁺ = 591

Preparation Example 13 Preparation of Compound ET3

Except that each starting material was the same as the reaction scheme, a compound represented by the formula ET3 was prepared by the same method as the preparation method of EC1 of Preparation Example 1.

MS [M + H] ⁺ = 586

Preparation Example 14 Preparation of Compound ET4

Except that each starting material was the same as the reaction scheme, a compound represented by the formula ET4 was prepared by the same method as the preparation method of EC1 of Preparation Example 1.

MS [M + H] ⁺ = 487

Example 1-1

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

The following HI-A compound was thermally vacuum deposited to a thickness of 600 kPa on the prepared ITO transparent electrode to form a hole injection layer. 50 정 of the following HAT compound and 60 하기 of the following HT-A compound were sequentially vacuum deposited on the hole injection layer to form a hole transport layer.

Subsequently, the BH compound and the following BD compound were vacuum-deposited at a weight ratio of 25: 1 on the hole transport layer to form a light emitting layer to form a film thickness of 200 Pa.

The compound EC1 was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 50 kHz. The compound ET1 and the following LiQ compound were vacuum deposited on the hole blocking layer in a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 300 kPa. The cathode was formed by sequentially depositing lithium fluoride (LiF) and aluminum at a thickness of 1000 상 에 on the electron injection and transport layer sequentially.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 Å / sec, and the aluminum was 2 Å / sec. ^An organic light-emitting device was manufactured by maintaining ⁻⁷ to 5 × 10 ⁻⁵ torr.

Examples 1-2 to 1-20 and Comparative Examples 1-1 to 1-15

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Table 1 instead of the compound EC1 and ET1 of Example 1-1.

For the organic light emitting diodes manufactured in Examples 1-1 to 1-20 and Comparative Examples 1-1 to 1-15, the driving voltage and the luminous efficiency were measured at a current density of 10 mA / cm ² , and 20 mA / cm ^The time T90 of 90% of the initial luminance at the current density of ² was measured. The results are shown in Table 1 below.

Classification (Compound) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10 mA / cm ² ) Color coordinates
(x, y) Life (h)
(T90 at 20 mA / cm ² ) Example 1-1 EC1 ET1 3.65 5.27 (0.135, 0.088) 240 Example 1-2 EC2 ET1 3.61 5.38 (0.135, 0.089) 227 Example 1-3 EC3 ET1 3.62 5.16 (0.135, 0.087) 249 Example 1-4 EC4 ET1 3.63 5.31 (0.133, 0.088) 228 Example 1-5 EC5 ET1 3.74 5.05 (0.135, 0.089) 257 Example 1-6 EC6 ET2 3.60 5.19 (0.135, 0.087) 235 Example 1-7 EC7 ET2 3.56 5.43 (0.135, 0.088) 217 Example 1-8 EC8 ET2 3.59 5.16 (0.133, 0.088) 238 Example 1-9 EC9 ET2 3.56 5.31 (0.135, 0.089) 229 Example 1-10 EC10 ET2 3.65 5.21 (0.135, 0.087) 219 Example 1-11 EC1 ET3 3.83 5.33 (0.135, 0.088) 228 Example 1-12 EC2 ET3 3.79 5.44 (0.133, 0.088) 216 Example 1-13 EC3 ET3 3.80 5.21 (0.135, 0.088) 236 Example 1-14 EC4 ET3 3.81 5.36 (0.133, 0.088) 217 Example 1-15 EC5 ET3 3.92 5.10 (0.135, 0.089) 244 Example 1-16 EC6 ET4 3.67 5.04 (0.135, 0.087) 216 Example 1-17 EC7 ET4 3.64 5.26 (0.135, 0.088) 199 Example 1-18 EC8 ET4 3.66 5.00 (0.133, 0.088) 219 Example 1-19 EC9 ET4 3.63 5.15 (0.135, 0.089) 210 Example 1-20 EC10 ET4 3.73 5.05 (0.135, 0.087) 202 Comparative Example 1-1 EC1 ET-B 3.68 4.22 (0.135, 0.088) 48 Comparative Example 1-2 EC2 ET-B 3.65 4.31 (0.135, 0.089) 45 Comparative Example 1-3 EC3 ET-B 3.65 4.13 (0.135, 0.087) 50 Comparative Example 1-4 EC4 ET-B 3.66 4.25 (0.133, 0.088) 46 Comparative Example 1-5 EC5 ET-B 3.77 4.04 (0.135, 0.089) 51 Comparative Example 1-6 EC6 ET-B 3.64 4.15 (0.135, 0.087) 47 Comparative Example 1-7 EC7 ET-B 3.60 4.34 (0.135, 0.088) 43 Comparative Example 1-8 EC8 ET-B 3.63 4.13 (0.133, 0.088) 48 Comparative Example 1-9 EC9 ET-B 3.59 4.25 (0.135, 0.089) 46 Comparative Example 1-10 EC10 ET-B 3.69 4.17 (0.135, 0.087) 44 Comparative Example 1-11 ET-A ET1 4.01 4.37 (0.135, 0.088) 36 Comparative Example 1-12 ET-A ET2 3.96 4.32 (0.135, 0.088) 35 Comparative Example 1-13 ET-A ET3 4.21 4.26 (0.133, 0.088) 34 Comparative Example 1-14 ET-A ET4 4.04 4.13 (0.135, 0.089) 32 Comparative Example 1-15 ET-A ET-B 4.44 4.00 (0.133, 0.088) 54

When comparing Examples 1-1 to 1-20 and Comparative Examples 1-1 to 1-15 in Table 1, the organic light emitting device to which the formula 1 and formula 3 according to the present specification is applied, only Formula 1 or Formula 3 It is remarkably excellent in lifespan compared with an organic light emitting element.

Example 2-1

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

The following HI-A compound was thermally vacuum deposited to a thickness of 600 kPa on the prepared ITO transparent electrode to form a first hole injection layer. The following HAT compound 50 Hz and the following HT-A compound 60 Hz were sequentially vacuum deposited on the first hole injection layer to form a first hole transport layer.

Subsequently, a BH compound and a BD compound were vacuum deposited on the first hole transport layer at a film thickness of 200 Pa at a weight ratio of 25: 1 to form a first light emitting layer.

The compound EC1 was vacuum-deposited on the first emission layer to form a first hole blocking layer having a thickness of 50 μs. The compound ET1 and the following LiQ compound were vacuum deposited on the first hole blocking layer in a weight ratio of 1: 1 to form a first electron injection and transport layer at a thickness of 200 μs.

Compound ET-C and a lithium compound were vacuum deposited on the first electron injection and transport layer at a film thickness of 100 Pa to form an electron charge generating layer. The second hole injection layer was formed by thermally vacuum depositing a HI-A compound to a thickness of 100 kPa on the electron charge generating layer.

The second HAT compound 50 μs and the following HT-A compound 60 μs were sequentially vacuum deposited on the second hole injection layer to form a second hole transport layer.

Subsequently, a BH compound and a BD compound were vacuum deposited on the second hole transport layer at a film thickness of 200 Pa at a weight ratio of 25: 1 to form a second light emitting layer.

Compound EC1 was vacuum deposited on the second light emitting layer to form a hole blocking layer having a thickness of 50 kHz. The compound ET1 and the following LiQ compound were vacuum deposited on the second hole blocking layer at a weight ratio of 1: 1 to form a second electron injection and transport layer at a thickness of 200 μs. A cathode was formed by sequentially depositing lithium fluoride (LiF) and aluminum at a thickness of 1000 로 on the second electron injection and transport layer sequentially.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 Å / sec, and the aluminum was 2 Å / sec. ^An organic light-emitting device was manufactured by maintaining ⁻⁷ to 5 × 10 ⁻⁵ torr.

Examples 2-2 to 2-20 and Comparative Examples 2-1 to 2-15

An organic light emitting diode was manufactured according to the same method as Example 2-1 except for using the compound of Table 1 instead of the compound EC1 and ET1 of Example 2-1.

The driving voltage and the luminous efficiency of the organic light emitting diodes manufactured in Examples 2-2 to 2-20 and Comparative Examples 2-1 to 2-15 were measured at a current density of 10 mA / cm ² , and 20 mA / cm ^2. The time T90 of 90% of the initial luminance at the current density of was measured. The results are shown in Table 2 below.

Classification (Compound) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10 mA / cm ² ) Color coordinates
(x, y) Life (h)
(T90 at 20 mA / cm ² ) Example 2-1 EC1 ET1 7.25 12.12 (0.137, 0.124) 187 Example 2-2 EC2 ET1 7.17 12.37 (0.137, 0.124) 177 Example 2-3 EC3 ET1 7.19 11.87 (0.137, 0.123) 194 Example 2-4 EC4 ET1 7.21 12.21 (0.137, 0.125) 178 Example 2-5 EC5 ET1 7.42 11.62 (0.137, 0.124) 200 Example 2-6 EC6 ET2 7.15 11.94 (0.137, 0.124) 183 Example 2-7 EC7 ET2 7.07 12.49 (0.137, 0.123) 169 Example 2-8 EC8 ET2 7.13 11.87 (0.137, 0.125) 186 Example 2-9 EC9 ET2 7.07 12.21 (0.137, 0.124) 179 Example 2-10 EC10 ET2 7.25 11.98 (0.137, 0.124) 171 Example 2-11 EC1 ET3 7.60 12.26 (0.137, 0.123) 178 Example 2-12 EC2 ET3 7.52 12.51 (0.137, 0.125) 168 Example 2-13 EC3 ET3 7.54 11.98 (0.137, 0.124) 184 Example 2-14 EC4 ET3 7.56 12.33 (0.137, 0.124) 169 Example 2-15 EC5 ET3 7.78 11.73 (0.137, 0.123) 190 Example 2-16 EC6 ET4 7.28 11.59 (0.137, 0.125) 168 Example 2-17 EC7 ET4 7.23 12.10 (0.137, 0.124) 155 Example 2-18 EC8 ET4 7.27 11.50 (0.137, 0.124) 171 Example 2-19 EC9 ET4 7.21 11.85 (0.137, 0.123) 164 Example 2-20 EC10 ET4 7.40 11.62 (0.137, 0.124) 158 Comparative Example 2-1 EC1 ET-B 7.30 9.71 (0.137, 0.124) 37 Comparative Example 2-2 EC2 ET-B 7.25 9.91 (0.137, 0.124) 35 Comparative Example 2-3 EC3 ET-B 7.25 9.50 (0.137, 0.124) 39 Comparative Example 2-4 EC4 ET-B 7.27 9.78 (0.137, 0.125) 36 Comparative Example 2-5 EC5 ET-B 7.48 9.29 (0.137, 0.124) 40 Comparative Example 2-6 EC6 ET-B 7.23 9.55 (0.137, 0.124) 37 Comparative Example 2-7 EC7 ET-B 7.15 9.98 (0.137, 0.124) 34 Comparative Example 2-8 EC8 ET-B 7.21 9.50 (0.137, 0.125) 37 Comparative Example 2-9 EC9 ET-B 7.13 9.78 (0.137, 0.124) 36 Comparative Example 2-10 EC10 ET-B 7.32 9.59 (0.137, 0.124) 34 Comparative Example 2-11 ET-A ET1 7.96 10.05 (0.137, 0.123) 28 Comparative Example 2-12 ET-A ET2 7.86 9.94 (0.137, 0.123) 27 Comparative Example 2-13 ET-A ET3 8.36 9.80 (0.137, 0.124) 27 Comparative Example 2-14 ET-A ET4 8.02 9.50 (0.137, 0.124) 25 Comparative Example 2-15 ET-A ET-B 8.81 9.20 (0.137, 0.123) 42

When comparing Examples 2-1 to 2-20 and Comparative Examples 2-1 to 2-15 in Table 2, the organic light emitting device to which the formula 1 and formula 3 according to the present specification is applied, only the formula 1 or 3 It is remarkably excellent in lifespan compared with an organic light emitting element.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: hole transport layer
6: hole blocking layer or electron control layer
7: electron injection and transport layer

Claims (13)

A first electrode; A second electrode provided to face the first electrode; And a first organic material layer and a second organic material layer provided between the first electrode and the second electrode.
The first organic material layer includes a compound represented by Formula 1,
The second organic material layer is an organic light emitting device comprising a compound represented by the following formula (3):
[Formula 1]

In Chemical Formula 1,
X is O or S,
R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
At least one of R1 to R4 is represented by the formula (2A) or 2B,
n1 to n4 are each independently an integer of 1 to 4,
when n1 to n4 are each independently 2 or more, the substituents in parentheses are the same as or different from each other,
[Formula 2A]

[Formula 2B]

In Chemical Formulas 2A and 2B,
At least one of A1 to A3 is N, and the other is CH or combines with an adjacent group of L1, L2, L3, Ar4 and Ar5 to form a substituted or unsubstituted ring,
L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted ring,
Ar4 and Ar5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted ring,
Ar6 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, a is an integer from 0 to 5,
[Formula 3]

In Chemical Formula 3,
X 1 is N or CH,
Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group. The method according to claim 1,
Formula 1 is represented by any one of the following Formula 1-1 to Formula 1-5:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Chemical Formulas 1-1 to 1-5,
The definitions of X, R1 to R4, L1 to L3, A1 to A3, Ar4, Ar5 and n1 to n4 are the same as in claim 1, and the L1 ', L2', L3 ', A1', A2 ', A3', Ar4 'and Ar5' are the same as defined for L1, L2, L3, A1, A2, A3, Ar4 and Ar5, respectively. The method according to claim 1,
Formula 3 is an organic light emitting device represented by the following formula 3-1:
[Formula 3-1]

In Chemical Formula 3-1,
X1 'is N or CH,
Ar1 'and Ar2' are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group,
L is a direct bond; Or a substituted or unsubstituted divalent or trivalent aryl group,
Ar3 'is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
n5 is 1 or 2, and when n5 is 2, the substituents in parentheses are the same as or different from each other. The method according to claim 1, wherein at least one of Ar1 to Ar3 of Formula 3 is an aryl group substituted with a heterocyclic group; Or a substituted or unsubstituted heterocyclic group. The method according to claim 1,
Formula 1 is selected from the following structural formula organic light emitting device:

The method according to claim 1,
Formula 3 is an organic light emitting device is selected from the following structural formula:

The method according to claim 1,
The first organic material layer is an organic light emitting device that is a hole blocking layer or an electron control layer. The method according to claim 1,
The second organic material layer is an organic light emitting device that is an electron injection and transport layer. The method according to claim 1,
An organic light emitting device comprising at least two light emitting layers for emitting light of different wavelengths between the first electrode and the second electrode. The method according to claim 1,
At least two light emitting layers are disposed between the first electrode and the second electrode,
Wherein each light emitting layer independently comprises a fluorescent dopant or a phosphorescent dopant. The method according to claim 1,
At least two light emitting layers are disposed between the first electrode and the second electrode,
Either one light emitting layer comprises a fluorescent dopant, and the other light emitting layer comprises a phosphorescent dopant. The method according to claim 1,
Three or more light emitting layers are included between the first electrode and the second electrode,
Wherein each light emitting layer comprises a blue fluorescent light emitting layer. The method according to claim 12,
The three or more light emitting layers are provided in order in the direction from the first electrode to the second electrode.

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