KR102216430B1 - Multicyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a compound of Formula 1 and an organic light emitting device including the same.

Description

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

The present invention claims the benefit of the filing date of Korean Patent Application No. 10-2018-0084046 filed with the Korean Intellectual Property Office on July 19, 2018, the entire contents of which are incorporated herein.

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

In the present specification, an organic light-emitting device is a light-emitting device using an organic semiconductor material, and requires an 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 that forms an interface with the electrode by applying voltage or current to two or more electrodes, and operates 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 multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, the organic material layer is composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer, etc. I can lose. 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 Publication No. 2017-126443

In the present specification, a compound and an organic light emitting device including the same are described.

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

[Formula 1]

In Formula 1,

Cy1 to Cy4 are the same as or different from each other, and each independently substituted or unsubstituted benzene; Or a bicyclic or more condensed hydrocarbon ring including a substituted or unsubstituted alicyclic hydrocarbon ring, and at least one of Cy1 to Cy4 is a bicyclic or more condensed hydrocarbon ring including a substituted or unsubstituted alicyclic hydrocarbon ring,

R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alicyclic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,

n1 is an integer of 0 to 3, and when n1 is 2 or more, 2 or more R1s are the same as or different from each other.

Further, according to an exemplary embodiment of the present invention, the 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 aforementioned compound.

The compound of the present invention can be used as a material for an organic material layer of an organic light emitting device. In the case of manufacturing an organic light emitting device including the compound of the present invention, an organic light emitting device having high efficiency, low voltage and long life characteristics can be obtained, and when the compound of the present invention is included in the light emitting layer of the organic light emitting device, a high color gamut is achieved. Eggplant can manufacture an organic light emitting device.

1 and 2 show an example of an organic light emitting device according to the present invention.

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

The present specification provides a compound represented by the following formula (1). When the compound represented by the following Formula 1 is used in the organic material layer of the organic light-emitting device, the efficiency and lifespan characteristics of the organic light-emitting device are improved. In particular, conventional compounds having a high sublimation temperature have low stability of the compound, and thus the efficiency and lifespan of the device decreases when applied to a device. However, the compound represented by the following Formula 1 contains a cycloalkene ring in the molecule, so Since it has a sublimation temperature, it has high stability, and when applied to a device, it is possible to obtain a device having excellent efficiency and long life characteristics.

In addition, the compound represented by the following formula (1) contains a cycloalkene ring in the molecule, so that the solubility is increased and thus can be applied to a solution process.

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.

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

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 at which 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; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or no substituent. 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.

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

In the present specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

In the present specification, the silyl group may be represented by the formula of -SiYaYbYc, wherein Ya, Yb and Yc are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc., but is not limited thereto. Does not.

In the present specification, the boron group may be represented by the formula of -BYdYe, wherein Yd and Ye are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and the like.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group; Dimethylamine group; Ethylamine group; Diethylamine group; Phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methylanthracenylamine group; Diphenylamine group; N-phenylnaphthylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, and the like, but are not limited thereto.

In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the alkyl group in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is the same as the example of the aforementioned alkyl group. Specifically, the alkyl thioxy group is a methyl thioxy group; Ethyl thioxy group; tert-butyl thioxy group; Hexylthioxy group; Octylthioxy group, etc., as the alkyl sulfoxy group, mesyl; Ethyl sulfoxy group; Propyl sulfoxy group; Butyl sulfoxy group and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si, and Se as a hetero atom, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, and a carbazole group. However, it is not limited to these.

In the present specification, the description of the aryl group may be applied to the aromatic hydrocarbon ring.

In the present specification, the description of the cycloalkyl group may be applied to the aliphatic hydrocarbon ring.

In the present specification, the alicyclic hydrocarbon ring is a structure bonded in a ring shape, and refers to a ring that is not aromatic. Examples of the alicyclic hydrocarbon ring include cycloalkane, and the cycloalkane is a cyclic group that has a double bond in the hydrocarbon ring, but is not aromatic, and the number of carbons is not particularly limited, but the number of carbons is 3 to 60 It may be, and according to an exemplary embodiment, it may be 3 to 30. Examples of the cycloalkene include cyclopropene, cyclobutene, cyclopentene, and cyclohexene, but are not limited thereto.

In the present specification, the condensed ring of an aromatic hydrocarbon ring and an alicyclic hydrocarbon ring means that an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring form a condensed ring.

In the present specification, the condensed hydrocarbon ring may be monovalent or divalent. Specifically, when Cy1 and Cy2 are condensed hydrocarbon rings in the present formula (1), the condensed hydrocarbon ring corresponds to divalent, and when Cy3 and Cy4 are condensed hydrocarbon rings in the present formula (1), the condensed hydrocarbon ring is a monovalent group It corresponds.

According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3-C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A substituted or unsubstituted amine group; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

According to another exemplary embodiment, R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3-C30 cycloalkyl group; An amine group unsubstituted or substituted with an aryl group having 6 to 10 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 alicyclic hydrocarbon ring.

)이다.In another exemplary embodiment, R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted cyclohexyl group; Or substituted or unsubstituted tetrahydronaphthalene (tetrahydronaphthalene,

)to be.

According to another exemplary embodiment, R1 is hydrogen; heavy hydrogen; Methyl group; tert-butyl group; Cyclohexyl group; Or tetrahydronaphthalene.

According to an exemplary embodiment of the present specification, n1 is 0 or 1.

According to another exemplary embodiment, n1 is 1.

According to an exemplary embodiment of the present specification, Cy1 to Cy4 are the same as or different from each other, and each independently substituted or unsubstituted benzene; Or a condensed hydrocarbon ring having 6 to 60 carbon atoms including a substituted or unsubstituted alicyclic hydrocarbon ring, and at least two of Cy1 to Cy4 are 6 to 60 carbon atoms including a substituted or unsubstituted alicyclic hydrocarbon ring. It is a condensed hydrocarbon ring of two or more rings.

According to another exemplary embodiment, the Cy1 to Cy4 are the same as or different from each other, and each independently substituted or unsubstituted benzene; Or a condensed hydrocarbon ring having 10 to 30 carbon atoms including a substituted or unsubstituted alicyclic hydrocarbon ring, and at least two of Cy1 to Cy4 are 10 to 30 carbon atoms including a substituted or unsubstituted alicyclic hydrocarbon ring. It is a condensed hydrocarbon ring of two or more rings.

In another exemplary embodiment, Cy1 to Cy4 are the same as or different from each other, and each independently benzene substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms; Or a condensed hydrocarbon ring having 10 to 30 carbon atoms, including an alicyclic hydrocarbon ring unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, and two or more of Cy1 to Cy4 are substituted or provided with an alkyl group having 1 to 20 carbon atoms It is a condensed hydrocarbon ring of 2 or more rings having 10 to 30 carbon atoms including a cyclic alicyclic hydrocarbon ring.

According to another exemplary embodiment, the Cy1 to Cy4 are the same as or different from each other, and each independently substituted or unsubstituted benzene; Or a bicyclic or tricyclic condensed hydrocarbon ring including a substituted or unsubstituted alicyclic hydrocarbon ring, and at least two of Cy1 to Cy4 are a bicyclic or tricyclic condensed hydrocarbon ring including a substituted or unsubstituted alicyclic hydrocarbon ring to be.

In another exemplary embodiment, Cy1 to Cy4 are the same as or different from each other, and each independently benzene substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms; Or a bicyclic or tricyclic condensed hydrocarbon ring including an alicyclic hydrocarbon ring unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, and at least two of Cy1 to Cy4 are alicyclic substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms It is a bicyclic or tricyclic condensed hydrocarbon ring including a group hydrocarbon ring.

According to another exemplary embodiment, Cy1 to Cy4 are the same as or different from each other, and each independently benzene substituted or unsubstituted with a methyl group or a butyl group; Or a bicyclic or tricyclic condensed hydrocarbon ring containing an alicyclic hydrocarbon ring unsubstituted or substituted with a methyl group or a butyl group, and at least two of Cy1 to Cy4 include an alicyclic hydrocarbon ring unsubstituted or substituted with a methyl group or a butyl group. It is a bicyclic or tricyclic fused hydrocarbon ring.

); 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 다이하이드로아세나프틸렌(dihydroacenaphthylene,

); 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 테트라하이드로나프탈렌(tetrahydronaphthalene,

); 또는 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 다이하이드로인덴(dihydroindene,

)이며, Cy1 내지 Cy4 중 2 이상은 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 다이하이드로페날렌; 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 다이하이드로아세나프틸렌; 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 테트라하이드로나프탈렌; 또는 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 다이하이드로인덴이다.In another exemplary embodiment, Cy1 to Cy4 are the same as or different from each other, and each independently benzene substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms; Dihydrophenalene unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms (dihydrophenalene,

); Dihydroacenaphthylene unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms (dihydroacenaphthylene,

); Tetrahydronaphthalene unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms (tetrahydronaphthalene,

); Or dihydroindene unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms (dihydroindene,

), and at least two of Cy1 to Cy4 are dihydrophenalene unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms; Dihydroacenaphthylene unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms; Tetrahydronaphthalene unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms; Or dihydroindene unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, Cy1 to Cy4 are the same as or different from each other, and each independently benzene unsubstituted or substituted with a butyl group; Dihydrophenalene; Dihydroacenaphthylene; Tetrahydronaphthalene; Or dihydroindene substituted with a methyl group, and at least two of Cy1 to Cy4 are dihydrophenalene; Dihydroacenaphthylene; Tetrahydronaphthalene; Or dihydroindene substituted with a methyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 4.

[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,

R1 and n1 are as defined in Formula 1,

Y1 to Y4; And Y5 to Y8 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, respectively,

X1 and X2; X3 and X4; X5 and X6; And two or more selected from the group consisting of X7 and X8 are bonded to each other to form a substituted or unsubstituted alicyclic hydrocarbon ring, respectively,

Z1 to Z3; Z4 to Z6; Z7 to Z9; And two or more selected from the group consisting of Z10 to Z12 are bonded to each other to form a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an alicyclic hydrocarbon ring, respectively,

Z1 to Z3; Z4 to Z6; Z7 to Z9; And at least one of the rings formed by bonding of two or more selected from the group consisting of Z10 to Z12 with each other is an alicyclic hydrocarbon ring,

R2 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n6, n7, n12 and n13 are each an integer of 0 to 2, and when n6, n7, n12 and n13 are each 2, the substituents in the two parentheses are the same or different from each other,

n4 and n5 are each an integer of 0 to 7,

n8 and n9 are each an integer of 0 to 3,

n2 and n3 are each an integer of 0 to 4,

When n2, n3, n4, n5, n8 and n9 are each 2 or more, the substituents in the plurality of parentheses are the same or different from each other.

In the exemplary embodiment of the present specification, R2 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3-C30 cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

In the exemplary embodiment of the present specification, R2 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

According to another exemplary embodiment, the R2 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted silyl group.

According to an exemplary embodiment of the present invention, the R2 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; An amine group unsubstituted or substituted with an aryl group or a heteroaryl group; Or a silyl group unsubstituted or substituted with an alkyl group or an aryl group.

In another exemplary embodiment, R2 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted terbutyl group; A substituted or unsubstituted phenyl group; Trimethylsilyl group; Or an amine group substituted with an aryl group.

According to another exemplary embodiment, the R2 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group having 1 to 20 carbon atoms.

In another exemplary embodiment, R2 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Or tert-butyl group.

According to an exemplary embodiment of the present specification, n2 to n13 are 0 or 1, respectively.

According to an exemplary embodiment of the present specification, the Y1 to Y4; And Y5 to Y8 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, respectively.

In another exemplary embodiment, the Y1 to Y4; And Y5 to Y8 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms, respectively.

According to another exemplary embodiment, Y1 to Y4 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms, and Y5 to Y8 are bonded to each other to form a substituted or unsubstituted C6 to C6. It forms an aromatic hydrocarbon ring of 60.

According to another exemplary embodiment, Y1 to Y4 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, and Y5 to Y8 are bonded to each other to form a substituted or unsubstituted C6 to C6. It forms 30 aromatic hydrocarbon rings.

In another exemplary embodiment, the Y1 to Y4; And Y5 to Y8 are bonded to each other to form a substituted or unsubstituted benzene ring, respectively.

According to another exemplary embodiment, Y1 to Y4 are bonded to each other to form a substituted or unsubstituted benzene ring, and Y5 to Y8 are bonded to each other to form a substituted or unsubstituted benzene ring.

In another exemplary embodiment, Y1 to Y4 are bonded to each other to form a benzene ring, and Y5 to Y8 are bonded to each other to form a benzene ring.

In an exemplary embodiment of the present specification, Formula 2 is represented by the following Formula 5.

[Formula 5]

In Formula 5,

R1 to R5 and n1 to n5 are as defined in Formula 2,

Cy11 and Cy12 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, Cy11 and Cy12 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms.

In another exemplary embodiment, Cy11 and Cy12 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

According to another exemplary embodiment, Cy11 and Cy12 are the same as or different from each other, and each independently a substituted or unsubstituted benzene ring.

In another exemplary embodiment, Cy11 and Cy12 are each a benzene ring.

In the exemplary embodiment of the present specification, X1 and X2; X3 and X4; X5 and X6; And two or more selected from the group consisting of X7 and X8 are bonded to each other to form a substituted or unsubstituted alicyclic hydrocarbon ring having 3 to 60 carbon atoms, respectively.

According to another exemplary embodiment, the X1 and X2; X3 and X4; X5 and X6; And two or more selected from the group consisting of X7 and X8 are bonded to each other to form a substituted or unsubstituted alicyclic hydrocarbon ring having 3 to 30 carbon atoms, respectively.

According to another exemplary embodiment, the X1 and X2; X3 and X4; X5 and X6; And two or more selected from the group consisting of X7 and X8 are bonded to each other to form an alicyclic hydrocarbon ring having 3 to 30 carbon atoms, each unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

In another embodiment, the X1 and X2; X3 and X4; X5 and X6; And two or more selected from the group consisting of X7 and X8 are bonded to each other to form a substituted or unsubstituted cycloalkene ring having 3 to 30 carbon atoms, respectively.

According to another exemplary embodiment, the X1 and X2; X3 and X4; X5 and X6; And two or more selected from the group consisting of X7 and X8 are bonded to each other to form a cycloalkene ring having 3 to 30 carbon atoms, each unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

In another embodiment, the X1 and X2; X3 and X4; X5 and X6; And two or more selected from the group consisting of X7 and X8 are bonded to each other to form a substituted or unsubstituted cyclopentene, respectively; Or to form a substituted or unsubstituted cyclohexene.

According to another exemplary embodiment, the X1 and X2; X3 and X4; X5 and X6; And two or more selected from the group consisting of X7 and X8 are bonded to each other to form a substituted or unsubstituted cyclopentene, respectively, to form a substituted or unsubstituted dihydroindene, or to form a substituted or unsubstituted cyclohexene. Or it forms unsubstituted tetrahydronaphthalene.

According to another exemplary embodiment, the X1 and X2; X3 and X4; X5 and X6; And cyclopentene unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms by bonding of at least two selected from the group consisting of X7 and X8; Or to form a substituted or unsubstituted cyclohexene with an alkyl group having 1 to 20 carbon atoms.

In another embodiment, the X1 and X2; X3 and X4; X5 and X6; And cyclopentene wherein two or more selected from the group consisting of X7 and X8 are bonded to each other and each substituted with a methyl group; Or to form cyclohexene.

According to another exemplary embodiment, Chemical Formula 3 is represented by any one of Chemical Formulas 6 to 8.

[Formula 6]

[Formula 7]

[Formula 8]

In Formulas 6 to 8,

R1, R6 to R9, n1 and n6 to n9 are as defined in Formula 3,

Cy13 to Cy16 are the same as or different from each other, and each independently a substituted or unsubstituted alicyclic hydrocarbon ring.

According to an exemplary embodiment of the present specification, Cy13 to Cy16 are the same as or different from each other, and each independently a substituted or unsubstituted alicyclic hydrocarbon ring having 3 to 60 carbon atoms.

According to another exemplary embodiment, Cy13 to Cy16 are the same as or different from each other, and each independently a substituted or unsubstituted alicyclic hydrocarbon ring having 3 to 30 carbon atoms.

According to another exemplary embodiment, Cy13 to Cy16 are the same as or different from each other, and are each independently an alicyclic hydrocarbon ring having 3 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

In another exemplary embodiment, Cy13 to Cy16 are the same as or different from each other, and each independently a substituted or unsubstituted cycloalkene ring having 3 to 30 carbon atoms.

According to another exemplary embodiment, Cy13 to Cy16 are the same as or different from each other, and each independently a cycloalkene ring having 3 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

In another exemplary embodiment, Cy13 to Cy16 are the same as or different from each other, and each independently substituted or unsubstituted cyclopentene; Or a substituted or unsubstituted cyclohexene.

In another exemplary embodiment, Cy13 to Cy16 are the same as or different from each other, and each independently forms a substituted or unsubstituted cyclopentene to form a substituted or unsubstituted dihydroindene, or a substituted or unsubstituted Formed cyclohexene to form substituted or unsubstituted tetrahydronaphthalene.

According to another exemplary embodiment, Cy13 to Cy16 are the same as or different from each other, and each independently cyclopentene substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms; Or it is a cyclohexene substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

In another exemplary embodiment, Cy13 to Cy16 are the same as or different from each other, and each independently cyclopentene substituted with a methyl group; Or cyclohexene.

According to an exemplary embodiment of the present specification, the Z1 to Z3; Z4 to Z7; Z8 to Z10; And two or more selected from the group consisting of Z11 to Z13 are bonded to each other to form a condensed ring of a substituted or unsubstituted substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms and an alicyclic hydrocarbon ring having 3 to 60 carbon atoms, respectively. .

According to another exemplary embodiment, the Z1 to Z3; Z4 to Z7; Z8 to Z10; And two or more selected from the group consisting of Z11 to Z13 are bonded to each other to form a condensed ring of a substituted or unsubstituted substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms and an alicyclic hydrocarbon ring having 3 to 30 carbon atoms, respectively. .

In another exemplary embodiment, the Z1 to Z3; Z4 to Z6; Z7 to Z9; And two or more selected from the group consisting of Z10 to Z12 are bonded to each other to form a substituted or unsubstituted tetrahydronaphthalene; Or a substituted or unsubstituted dihydroindene is formed.

According to another exemplary embodiment, the Z1 to Z3; Z4 to Z6; Z7 to Z9; And two or more selected from the group consisting of Z10 to Z12 are bonded to each other to form tetrahydronaphthalene to form dihydrophenalene, or to form dihydroindene to form dihydroacenaphthylene.

According to an exemplary embodiment of the present specification, Chemical Formula 4 is represented by the following Chemical Formula 9 or Chemical Formula 10.

[Formula 9]

[Formula 10]

In Formulas 9 and 10,

R1, R10, R11 to R13, n1, n12 and n13 are as defined in Formula 4,

R14 to R17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n14 and n15 are each an integer of 0 to 4, n16 and n17 are each an integer of 0 to 5, and when n14 to n17 are each 2 or more, the substituents in a plurality of parentheses are the same or different from each other,

p1 to p4 are 1 or 2, respectively.

According to an exemplary embodiment of the present specification, R14 to R17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3-C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

In another exemplary embodiment, R14 to R17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

According to another exemplary embodiment, R14 to R17 are hydrogen.

According to an exemplary embodiment of the present specification, n14 to n17 are 0 or 1, respectively.

According to an exemplary embodiment of the present specification, p1 and p2 are 1 or 2, respectively.

According to an exemplary embodiment of the present specification, p3 and p4 are 1 or 2, respectively.

In the exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following structures.

The substituent of the compound of Formula 1 may be bonded by a method known in the art, and the type, position, or number of the substituent may be changed according to techniques known in the art.

The conjugation length and the energy band gap of the compound are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy band gap.

In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In addition, in the present invention, the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure of the above structure.

In addition, by introducing various substituents into the core structure of the above-described structure, a compound having the inherent characteristics of the introduced substituent can be synthesized. For example, by introducing a substituent mainly used for the hole injection layer material, the hole transport material, the light emitting layer material and the electron transport layer material used in the manufacture of the organic light emitting device into the core structure, it is possible to synthesize a material that satisfies the conditions required by each organic material layer. I can.

In addition, the organic light emitting device according to the present invention includes 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.

The organic light-emitting device of the present invention may be manufactured by a conventional method and material of an organic light-emitting device, except that one or more organic material layers are formed by using the above-described compound.

The compound 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, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

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

In the organic light emitting device of the present invention, the organic material layer may include at least one of an electron transport layer, an electron injection layer, and a layer that simultaneously injects and transports electrons, and at least one of the layers is represented by Formula 1 above. It may contain a compound.

In another organic light emitting device, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by Formula 1 above.

In the organic light emitting device of the present invention, the organic material layer may include at least one of a hole injection layer, a hole transport layer, and a layer that simultaneously injects and transports holes, and at least one of the layers is represented by Formula 1 above. It may contain a compound.

In another organic light emitting device, the organic material layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include a compound represented by Formula 1 above.

In another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 1 above. As an example, the compound represented by Formula 1 may be included as a dopant of the emission layer.

In the exemplary embodiment of the present specification, the organic light-emitting device is a green organic light-emitting device in which the emission layer includes the compound represented by Formula 1 as a dopant.

According to the exemplary embodiment of the present specification, the organic light-emitting device is a red organic light-emitting device in which the emission layer includes the compound represented by Formula 1 as a dopant.

In another exemplary embodiment, the organic light-emitting device is a blue organic light-emitting device in which the emission layer includes the compound represented by Formula 1 as a dopant.

As another example, the organic material layer including the compound represented by Formula 1 may include the compound represented by Formula 1 as a dopant, and may include an organic compound such as an anthracene compound as a host.

As another example, the organic material layer including the heterocyclic compound represented by Formula 1 may include the compound represented by Formula 1 as a dopant, and may include a fluorescent host or a phosphorescent host.

In another exemplary embodiment, the organic material layer comprising the heterocyclic compound represented by Formula 1 includes the compound represented by Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals, or A metal compound may be included as a dopant.

As another example, the organic material layer including the compound represented by Formula 1 includes the compound represented by Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and can be used together with an iridium-based (Ir) dopant. have.

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

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

(1) Anode/Hole Transport Layer/Light-Emitting Layer/Anode

(2) Anode/Hole Injection Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(3) Anode/Hole injection layer/Hole buffer layer/Hole transport layer/Light emitting layer/Anode

(4) Anode/hole transport layer/light-emitting layer/electron transport layer/cathode

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

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

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

(8) Anode/Hole injection layer/Hole buffer layer/Hole transport layer/Light emitting layer/Electron transport layer/Anode

(9) Anode/Hole injection layer/Hole buffer layer/Hole transport layer/Light emitting layer/Electron transport layer/Electron injection layer/Anode

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

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

(12) Anode/Hole injection layer/Hole transport layer/Electron suppression layer/Light-emitting layer/Electron transport layer/Anode

(13) Anode/Hole Injection Layer/Hole Transport Layer/Electron Suppression Layer/Emitting Layer/Electron Transport Layer/Electron Injection Layer/Anode

(14) Anode/Hole Transport Layer/Light-Emitting Layer/Hole Suppression Layer/Electron Transport Layer/Anode

(15) Anode/Hole Transport Layer/Light-Emitting Layer/Hole Suppression Layer/Electron Transport Layer/Electron Injection Layer/Anode

(16) Anode/Hole Injection Layer/Hole Transport Layer/Light-Emitting Layer/Hole Suppression Layer/Electron Transport Layer/Anode

(17) Anode/Hole injection layer/Hole transport layer/Light emitting layer/Hole suppression layer/Electron transport layer/Electron injection layer/Anode

(18) Anode/Hole injection layer/Hole transport layer/Electron suppression layer/Emitting layer/Hole blocking layer/Electron injection and transport layer/Anode

The structure of the organic light-emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.

The structure of the organic light-emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

In FIG. 1, a hole injection layer (5), a hole transport layer (6), an electron suppression layer (7), a light emitting layer (3), a first electron transport layer (8), and a second electron transport layer are shown on the substrate (1) and the anode (2). The structure of the organic light emitting device in which (9) and the cathode (4) are sequentially stacked is illustrated. In such a structure, the compound represented by Formula 1 may be included in the hole transport layer or hole injection layer 5, the light emitting layer 3, or the first electron transport layer 8.

FIG. 2 illustrates a structure of an organic light-emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In such a structure, the compound represented by Formula 1 may be included in the emission layer 3.

For example, the organic light-emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and uses a metal or conductive metal oxide or alloy thereof on a substrate. From the group consisting of a hole injection layer, a hole transport layer, a layer for simultaneous hole transport and hole injection, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer for simultaneously electron transport and electron injection. After forming an organic material layer including one or more selected layers, it can be prepared 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.

The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, etc., but is not limited thereto and may have a single layer structure. In addition, the organic material layer is made of a variety of polymer materials, and is used in a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made in layers.

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. 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.

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 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 multi-layered materials such as LiF/Al or LiO ₂ /Al, but are 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 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.

A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.

An electron suppressing layer may be provided between the hole transport layer and the light emitting layer. The electron suppressing layer may be formed of the above-described spiro compound or a material known in the art.

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.

Examples of the host material for the light emitting layer include condensed aromatic ring derivatives or heterocyclic compounds. 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.

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, a phosphor such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, it is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant is a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distillbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.

A hole inhibiting layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.

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 include Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The thickness of the electron transport layer may be 1 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 that can be.

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.

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

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

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

Synthesis Example 1. Synthesis of Compound 1

1) Synthesis of Intermediate 1

Under a nitrogen atmosphere, 3-(tert-butyl)aniline 40g, 6-bromo-2,3-dihydro-1H-phenalin 26.9g, sodium-tert-butoxide 37.3g, bis(tri-tert-butylphosphine ) 0.8 g of palladium (0) was added to 600 ml of toluene and stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 35 g of Intermediate 1. (Yield 71%). MS[M+H]+ = 316

2) Synthesis of Intermediate 2

In a nitrogen atmosphere, 33.3 g of intermediate 2, 15 g of 1,3,-dibromo-2-chloro-5 methylbenzene, 10.1 g of sodium-tert-butoxide, 0.27 g of bis(tri-tert-butylphosphine) palladium(0) Was added to 500 ml of toluene and stirred under reflux for 6 hours. After extraction after completion of the reaction, 24.0 g of intermediate 2 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 60%). MS[M+H]+ = 754

3) Synthesis of compound 1

In a nitrogen atmosphere, 8 g of Intermediate 2 was added to 120 ml of toluene and then lowered to 0 ^O C, and then 25.0 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 2 ml of boron tribromide was added dropwise and raised to 60 ^O C, followed by stirring for 12 hours. After the reaction was completed and extracted, 2.0 g of compound 1 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 26%). MS[M+H]+ = 727

Synthesis Example 2. Synthesis of Compound 2

1) Synthesis of Intermediate 3

N-(o-tolyl)-2,3-dihydro-1H-phenalen-6-amine 28.8 g, 1,3,-dibromo-2-chloro-5 methylbenzene 15 g, sodium-tert- under nitrogen atmosphere After adding 20.3 g of butoxide and 0.3 g of bis (tri-tert-butylphosphine) palladium (0) into 500 ml of toluene, the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, followed by purification using an ethyl acetate:hexane column to obtain 23 g of intermediate 3. (Yield 65%). MS[M+H]+ = 670

2) Synthesis of compound 2

In a nitrogen atmosphere, 8 g of intermediate 3 was added to 120 ml of toluene and then lowered to 0 ^O C, and then 28.1 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 2.3 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction after completion of the reaction, 2.1g of compound 2 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 27%). MS[M+H]+ = 643

Synthesis Example 3. Synthesis of Compound 3

1) Synthesis of Intermediate 4

20.8 g of bis(5,6,7,8-tetrahydronaphthalen-1-yl)amine, 2-(3,5-dibromo-4-chlorophenyl)-1,2,3,4-tetra in nitrogen atmosphere Hydronaphthalene 15g, sodium-tert-butoxide 14.4g, bis(tri-tert-butylphosphine)palladium(0) 0.2g was added to 500ml of toluene, followed by reflux stirring for 4 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 21 g of Intermediate 4. (Yield 71%). MS[M+H]+ = 794

2) Synthesis of compound 3

In a nitrogen atmosphere, 8 g of intermediate 4 was added to 120 ml of toluene and then lowered to 0 ^O C, and then 23.7 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 2.0 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After the reaction was completed and extracted, 1.9 g of compound 3 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 25%). MS[M+H]+ = 767

Synthesis Example 4. Synthesis of Compound 4

1) Synthesis of Intermediate 5

3,3-dimethyl-N-phenyl-2,3-dihydro-1H-inden-4-amine 17.8 g, 1-(3,5-dibromo-4-chlorophenyl)-1,2 under nitrogen atmosphere 15 g of 3,4-tetrahydronaphthalene, 14.4 g of sodium-tert-butoxide, and 0.2 g of bis(tri-tert-butylphosphine)palladium(0) were added to 500 ml of toluene, followed by reflux stirring for 4 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 18.5 g of Intermediate 5. (Yield 69%). MS[M+H]+ = 714

2) Synthesis of compound 4

In a nitrogen atmosphere, 8 g of Intermediate 5 was added to 120 ml of toluene and then lowered to 0 ^O C, and then 26.4 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 2.2 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction was completed after the reaction was completed, 2.1 g of compound 4 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 27%). MS[M+H]+ = 687

Synthesis Example 5. Synthesis of Compound 5

1) Synthesis of Intermediate 6

Under nitrogen atmosphere N-(3-(tert-butyl)phenyl)-2,3-dihydro-1H-phenalen-6-amine 40g, 1-bromo-2,3-dichlorobenzene 28.6g, sodium- After adding 30.5 g of tert-butoxide and 0.7 g of bis(tri-tert-butylphosphine) palladium (0) to 600 ml of toluene, the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 39 g of Intermediate 6. (Yield 67%).

MS[M+H]+ = 461

2) Synthesis of Intermediate 7

15 g of intermediate 6, 7.3 g of N-phenyl-5,6,7,8-tetrahydronaphthalen-1-amine, 6.3 g of sodium-tert-butoxide, bis(tri-tert-butylphosphine)palladium ( 0) 0.17g was added to 300ml of toluene and stirred under reflux for 6 hours. After the reaction was completed and extracted, 15.0 g of intermediate 7 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 71%). MS[M+H]+ = 648

3) Synthesis of compound 5

In a nitrogen atmosphere, 8 g of Intermediate 7 was added to 120 ml of toluene, and after lowering to 0 ^O C, 29.1 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 2.3 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction after completion of the reaction, 2.2g of compound 5 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 29%). MS[M+H]+ = 621

Synthesis Example 6. Synthesis of Compound 6

1) Synthesis of Intermediate 8

2,2-dimethyl-N-(o-tolyl)-2,3-dihydro-1H-inden-5-amine 40 g, 1-bromo-2,3-dichlorobenzene 35.9 g, sodium under nitrogen atmosphere 38.2 g of -tert-butoxide and 0.8 g of bis(tri-tert-butylphosphine) palladium (0) were added to 600 ml of toluene and stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 41 g of Intermediate 8. (Yield 65%). MS[M+H]+ = 397

2) Synthesis of Intermediate 9

15 g of intermediate 8 under nitrogen atmosphere, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-2,2-dimethyl-2,3-dihydro-1H-indene 14.0 g of -5-amine, 7.3 g of sodium-tert-butoxide, and 0.19 g of bis (tri-tert-butylphosphine) palladium (0) were added to 300 ml of toluene, followed by reflux stirring for 6 hours. After the reaction was completed and extracted, 19.0g of intermediate 9 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 69%). MS[M+H]+ = 730

3) Synthesis of compound 6

In a nitrogen atmosphere, 8 g of Intermediate 9 was added to 120 ml of toluene and then lowered to 0 ^O C, and then 25.8 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 2.1 ml of boron tribromide was added dropwise and raised to 60 ^O C, followed by stirring for 12 hours. After extraction was completed after the reaction was completed, 2.1 g of compound 6 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 27%). MS[M+H]+ = 703

Synthesis Example 7. Synthesis of Compound 7

1) Synthesis of Intermediate 10

N-(3-(tert-butyl)phenyl)-2,3-dihydro-1H-phenalen-6-amine 40 g, 1-bromo-2,3-dichloro-5-methyl-benzene under nitrogen atmosphere 30.4 g, sodium-tert-butoxide 30.5 g, bis (tri-tert-butylphosphine) palladium (0) 0.7 g was added to 600 ml of toluene and stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 42 g of intermediate 10. (Yield 70%). MS[M+H]+ = 475

2) Synthesis of Intermediate 11

15 g of intermediate 10, 7.5 g of 2,2-dimethyl-N-phenyl-2,3-dihydro-1H-inden-5-amine, 6.1 g of sodium-tert-butoxide, bis(tri-tert- After adding 0.16 g of butylphosphine) palladium (0) to 300 ml of toluene, the mixture was stirred under reflux for 6 hours. After extraction was completed after the reaction was completed, 15.0 g of intermediate 11 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 70%). MS[M+H]+ = 676

3) Synthesis of compound 7

In a nitrogen atmosphere, 8 g of Intermediate 11 was added to 120 ml of toluene and then lowered to 0 ^O C, and then 27.8 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 2.3 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction after completion of the reaction, 2.0 g of compound 7 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 26%). MS[M+H]+ = 649

Synthesis Example 8. Synthesis of Compound 8

1) Synthesis of Intermediate 12

Under a nitrogen atmosphere, N-phenyl-5,6,7,8-tetrahydronaphthalen-2-amine 40g, 1-bromo-2,3-dichlorobenzene 40.5g, sodium-tert-butoxide 43.0g, bis( After adding 0.9 g of tri-tert-butylphosphine) palladium (0) to 600 ml of toluene, the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 44 g of Intermediate 12. (Yield 67%). MS[M+H]+ = 368

2) Synthesis of Intermediate 13

In a nitrogen atmosphere, 15 g of intermediate 12, 11.5 g of bis(3-(tert-butyl)phenyl)amine, 7.8 g of sodium-tert-butoxide, 0.21 g of bis(tri-tert-butylphosphine)palladium(0), 300 ml of toluene The mixture was stirred under reflux for 6 hours after being put into After extraction was completed after the reaction was completed, 17 g of intermediate 13 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 68%). MS[M+H]+ = 614

3) Synthesis of compound 8

In a nitrogen atmosphere, 8 g of Intermediate 13 was added to 120 ml of toluene and then lowered to 0 ^O C, and then 30.7 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 2.5 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction after completion of the reaction, 2.1g of compound 8 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 27%). MS[M+H]+ = 587

Synthesis Example 9. Synthesis of Compound 9

1) Synthesis of Intermediate 14

N-(5,6,7,8-tetrahydronaphthalene-2-yl)-5,6,7,8-tetrahydronaphthalen-1-amine 40 g, 1-bromo-2,3-di under nitrogen atmosphere After adding 34.6 g of chloro-5-methylbenzene, 34.6 g of sodium-tert-butoxide, and 0.7 g of bis(tri-tert-butylphosphine)palladium(0) to 600 ml of toluene, the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 43 g of intermediate 14. (Yield 68%). MS[M+H]+ = 437

2) Synthesis of Intermediate 15

15 g of intermediate 14, 2,2-dimethyl-N-(o-tolyl)-2,3-dihydro-1H-inden-5-amine 8.6 g, sodium-tert-butoxide 6.6 g, bis( After adding 0.18 g of tri-tert-butylphosphine) palladium (0) to 300 ml of toluene, the mixture was stirred under reflux for 6 hours. After the reaction was completed and extracted, 14 g of intermediate 15 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 63%). MS[M+H]+ = 652

3) Synthesis of compound 9

In a nitrogen atmosphere, 8 g of Intermediate 15 was added to 120 ml of toluene and then lowered to 0 ^O C, and then 28.9 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 2.4 ml of boron tribromide was added dropwise and then raised to 60 ^O C, followed by stirring for 12 hours. After extraction was completed after the reaction was completed, 2.1 g of compound 9 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 29%). MS[M+H]+ = 625

Synthesis Example 10. Synthesis of Compound 10

1) Synthesis of Intermediate 16

N1,N1-bis(4-(tert-butyl)phenyl)-N3-(2,2-dimethyl-2,3-dihydro-1H-indene-4-yl)benzene-1,3- in a nitrogen atmosphere Diamine 40g, 1-bromo-2,3-dichloro-5-methylbenzene 18.6g, sodium-tert-butoxide 18.6g, bis(tri-tert-butylphosphine)palladium(0) 0.4g toluene After adding to 600ml, the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 38 g of intermediate 16. (73% yield).

MS[M+H]+ = 676

2) Synthesis of Intermediate 17

15 g of intermediate 16, N-(3-(tert-butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-4-amine 5.6 g, sodium-tert-butoxide under nitrogen atmosphere 4.3 g, bis (tri-tert-butylphosphine) 0.11 g of palladium (0) was added to 300 ml of toluene and stirred under reflux for 6 hours. After the reaction was completed and extracted, 14 g of intermediate 17 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 68%). MS[M+H]+ = 933

3) Synthesis of compound 10

In a nitrogen atmosphere, 8 g of Intermediate 17 was added to 120 ml of toluene, and after lowering to 0 ^O C, 20.2 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 1.7 ml of boron tribromide was added dropwise and raised to 60 ^O C, followed by stirring for 12 hours. After extraction was completed after the reaction was completed, 2.3 g of compound 10 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 30%). MS[M+H]+ = 907

Synthesis Example 11. Synthesis of Compound 11

1) Synthesis of Intermediate 18

2-(tert-butyl)-N1,N1-bis(4-(tert-butyl)phenyl)-N4-(2,2-dimethyl-2,3-dihydro-1H-indene-4- yl)benzene-1,4-diamine 40g, 1-bromo-2,3-dichloro-5-methylbenzene 16.8g, sodium-tert-butoxide 16.8g, bis(tri-tert-butylphosphine) After adding 0.4 g of palladium (0) to 600 ml of toluene, the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 41 g of intermediate 18. (Yield 76%). MS[M+H]+ = 774

2) Synthesis of Intermediate 19

15 g of intermediate 18 under nitrogen atmosphere, N-(3-(tert-butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-4-amine 4.9 g, sodium-tert-butoxide 3.8 g, bis (tri-tert-butylphosphine) 0.10 g of palladium (0) was added to 300 ml of toluene and stirred under reflux for 6 hours. After extraction after completion of the reaction, 12 g of Intermediate 19 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 60%). MS[M+H]+ = 1031

3) Synthesis of compound 11

In a nitrogen atmosphere, 8 g of Intermediate 19 was added to 120 ml of toluene and then lowered to 0 ^O C, and 18.3 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 1.5 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction after completion of the reaction, 2.2g of compound 11 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 28%). MS[M+H]+ = 1005

Synthesis Example 12. Synthesis of Compound 12

1) Synthesis of Intermediate 20

N-([1,1'-biphenyl]-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine 40 g, 1-bromo-5-(tert-butyl) under nitrogen atmosphere 37.7 g of -2,3-dichlorobenzene, 32.1 g of sodium-tert-butoxide, and 0.7 g of bis (tri-tert-butylphosphine) palladium (0) were added to 600 ml of toluene, followed by reflux stirring for 4 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 47 g of intermediate 20. (Yield 70%). MS[M+H]+ = 501

2) Synthesis of Intermediate 21

15 g of Intermediate 20 under nitrogen atmosphere, N1,N1-bis(2,2-dimethyl-2,3-dihydro-1H-inden-5yl)-N4-(o-tolyl)benzene-1,4-diamine 14.6 g, sodium-tert-butoxide 5.8g, bis(tri-tert-butylphosphine)palladium(0) 0.15g were added to 300ml of toluene, followed by reflux agitation for 6 hours. After extraction after completion of the reaction, 16 g of intermediate 21 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 56%). MS[M+H]+ = 951

3) Synthesis of compound 12

In a nitrogen atmosphere, 8 g of Intermediate 21 was added to 120 ml of toluene, lowered to 0 ^O C, and 19.8 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 1.6 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction was completed after the reaction was completed, 2.2 g of compound 12 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 28%). MS[M+H]+ = 925

Synthesis Example 13. Synthesis of Compound 13

1) Synthesis of Intermediate 22

Under nitrogen atmosphere, 2,2-dimethyl-N-(o-tolyl)-2,3-dihydro-1H-inden-5amine 40g, 3,5-dibromo-4-chlorophenol 23.85g, sodium-tert -38.3 g of butoxide and 0.4 g of bis (tri-tert-butylphosphine) palladium (0) were added to 600 ml of toluene and stirred under reflux for 6 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 29 g of intermediate 22. (Yield 58%). MS[M+H]+ = 628

2) Synthesis of Intermediate 23

In a nitrogen atmosphere, 25 g of intermediate 22, 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfanyl fluoride 10.7 ml, potassium carbonate 16.5 g were added to 400 ml methyl chloride. It was stirred at room temperature for 3 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 30 g of intermediate 23 (yield 85%). MS[M+H]+ = 910

3) Synthesis of Intermediate 24

In a nitrogen atmosphere, 25 g of intermediate 23, 4.7 g of diphenylamine, 26.9 g of cesium carbonate, 0.47 g of bis(dibenzylidineacetone) palladium (0), and 0.78 g of expos were added to 400 ml of xylene, followed by reflux agitation for 6 hours. . After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 15 g of intermediate 24 (yield 70%). MS[M+H]+ = 779

4) Synthesis of compound 13

In a nitrogen atmosphere, 8 g of Intermediate 24 was added to 120 ml of toluene and then lowered to 0 ^O C, and then 24.2 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 2.0 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction after completion of the reaction, 2.4 g of compound 13 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 31%). MS[M+H]+ = 752

Synthesis Example 14. Synthesis of Compound 14

1) Synthesis of Intermediate 25

N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-5-amine under nitrogen atmosphere 40g, 3-bromo-4,5-dichlorophenol 26.2g, sodium-tert-butoxide 26.0g, bis(tri-tert-butylphosphine)palladium(0) 0.6g in 600ml of toluene for 6 hours Stir at reflux during. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 38 g of intermediate 25. (Yield 66%). MS[M+H]+ = 531

2) Synthesis of Intermediate 26

In a nitrogen atmosphere, 30 g of intermediate 26, 15.9 g of bis(3-tert-butyl)phenyl)amine, 10.9 g of sodium-tert-butoxide, 0.3 g of bis(tri-tert-butylphosphine)palladium(0) were added to 600 ml of toluene. After adding, the mixture was stirred under reflux for 6 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 28 g of intermediate 26. (Yield 64%). MS[M+H]+ = 776

3) Synthesis of Intermediate 27

In a nitrogen atmosphere, 25g of Intermediate 26, 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfanylfluoride 8.7ml, potassium carbonate 13.4g were added to 400ml methyl chloride. It was stirred at room temperature for 3 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 29 g of intermediate 27 (yield 85%). MS[M+H]+ = 1058

4) Synthesis of Intermediate 28

In a nitrogen atmosphere, 25 g of Intermediate 27, 6.7 g of bis(4-(tert-butyl)phenyl)amine, 23.1 g of cesium carbonate, 0.41 g of bis(dibenzylidineacetone)palladium(0), 0.67 g of expos, 400 ml of xylene The mixture was stirred under reflux for 6 hours after being put into After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 17 g of intermediate 28 (yield 69%). MS[M+H]+ = 1039

5) Synthesis of compound 14

In a nitrogen atmosphere, 8 g of Intermediate 28 was added to 120 ml of toluene, and after lowering to 0 ^O C, 18.1 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 1.5 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction was completed after the reaction was completed, 2.3 g of compound 14 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 30%). MS[M+H]+ = 1013

Synthesis Example 15. Synthesis of Compound 15

1) Synthesis of Intermediate 29

2,2-dimethyl-N-(o-tolyl)-2,3-dihydro-1H-inden-5-amine 40 g, 3-bromo-4,5-dichlorophenol 38.5 g, sodium under nitrogen atmosphere After adding 38.2 g of -tert-butoxide and 0.8 g of bis(tri-tert-butylphosphine) palladium (0) to 600 ml of toluene, the mixture was stirred under reflux for 6 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 43 g of intermediate 29. (Yield 66%).

MS[M+H]+ = 413

2) Synthesis of Intermediate 30

In a nitrogen atmosphere, 30 g of intermediate 29, 4'-(tert-butyl)-N-(o-tolyl)-[1,1'-biphenyl]-4-amine 23.0 g, sodium-tert-butoxide 14.0 g, bis 0.4 g of (tri-tert-butylphosphine) palladium (0) was added to 600 ml of toluene and stirred under reflux for 6 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 31 g of intermediate 30. (Yield 62%). MS[M+H]+ = 692

3) Synthesis of Intermediate 31

In a nitrogen atmosphere, 25 g of intermediate 30, 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfanyl fluoride 9.7 ml, potassium carbonate 15.0 g were added to 400 ml of methyl chloride. It was stirred at room temperature for 3 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 28 g of intermediate 31 (yield 80%). MS[M+H]+ = 974

4) Synthesis of Intermediate 32

Intermediate 31 25g, N-(4-(tert-butyl)phenyl)-[1,1'-biphenyl]-4-amine 7.8g, cesium carbonate 25.1g, bis(dibenzylidineacetone)palladium under nitrogen atmosphere (0) 0.44 g and 0.73 g of EXPOS were added to 400 ml of xylene, followed by reflux agitation for 6 hours. After completion of the reaction, extraction was performed, followed by purification with an ethyl acetate:hexane column to obtain 17 g of intermediate 32 (yield 68%). MS[M+H]+ = 975

5) Synthesis of compound 15

In a nitrogen atmosphere, 8 g of Intermediate 32 was added to 120 ml of toluene and then lowered to 0 ^O C, and 19.3 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 1.6 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction was completed after the reaction was completed, 2.2 g of compound 15 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 28%). MS[M+H]+ = 949

Synthesis Example 16. Synthesis of Compound 16

1) Synthesis of Intermediate 33

N-phenyl-5,6,7,8-tetrahydronaphthalene 40g was obtained by using the same equivalent and conditions as in the synthesis method of Intermediate No. 25, 44g of intermediate 33 was obtained. (Yield 72%). MS[M+H]+ = 385

2) Synthesis of Intermediate 34

30 g of intermediate 33, N-(2,2-dimethyl-2,3-dihydro-1H-indene-5-yl)-1,2,3,4-tetrahydronaphthalen-1-amine 22.8 g under nitrogen atmosphere Using the same equivalent weight and conditions as in the synthesis method of Intermediate No. 26, 44 g of Intermediate 34 was obtained. (Yield 72%). MS[M+H]+ = 692

3) Synthesis of Intermediate 35

In a nitrogen atmosphere, 25 g of Intermediate 34 and 27 g of Intermediate 35 were obtained using the same equivalents and conditions as in the synthesis method of Intermediate No. 27. (Yield 75%). MS[M+H]+ = 922

4) Synthesis of Intermediate 36

In a nitrogen atmosphere, 20 g of intermediate 35 and 6.1 g of N-(4-(tert-butyl)phenyl)-5,6,7,8-tetrahydronaphthalen-1-amine were used in the same amount and conditions as in the synthesis method of intermediate 28 Thus, 15 g of intermediate 36 was obtained. (Yield 77%). MS[M+H]+ = 901

5) Synthesis of compound 16

In a nitrogen atmosphere, 8 g of Intermediate 36 was added to 120 ml of toluene, and after lowering to 0 ^O C, 20.9 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 1.8 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After the reaction was completed and extracted, 2.3 g of compound 16 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 30%). MS[M+H]+ = 875

Synthesis Example 17. Synthesis of Compound 17

1) Synthesis of Intermediate 37

2,2-dimethyl-N-(o-tolyl)-2,3-dihydro-1H-inden-5-amine 40g was used in the same amount and conditions as in the synthesis method of Intermediate No. 25 to obtain 45g of Intermediate 37. . (Yield 69%). MS[M+H]+ = 413

2) Synthesis of Intermediate 38

In a nitrogen atmosphere, 30 g of Intermediate 37 and 22.8 g of N4-(O-tolyl)-N1,N1-di-Pp-tolylbenzene-1,4-diamine were used in the same amount and conditions as the synthesis method of Intermediate No. 38g was obtained. (Yield 69%). MS[M+H]+ = 755

3) Synthesis of Intermediate 39

In a nitrogen atmosphere, 25 g of Intermediate 38 and 27 g of Intermediate 39 were obtained using the same equivalents and conditions as in the synthesis method of Intermediate No. 27. (79% yield). MS[M+H]+ = 1037

4) Synthesis of Intermediate 40

In a nitrogen atmosphere, 20 g of intermediate 39 and 5.7 g of N-(4-(tert-butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-5-amine were added to the synthesis method of intermediate 28 Using the same equivalent weight and conditions, 14 g of intermediate 40 was obtained. (Yield 70%) MS[M+H]+ = 1030

5) Synthesis of compound 17

In a nitrogen atmosphere, 8 g of intermediate 40 was added to 120 ml of toluene, and after lowering to 0 ^O C, 18.3 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 1.5 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction after completion of the reaction, 2.1g of compound 17 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 27%) MS[M+H]+ = 1004

Synthesis Example 18. Synthesis of Compound 18

1) Synthesis of Intermediate 41

2,2-dimethyl-N-(o-tolyl)-2,3-dihydro-1H-inden-5-amine 40g was used in the same amount and conditions as in the synthesis method of Intermediate No. 20 to obtain 46g of intermediate 41. . (Yield 64%). MS[M+H]+ = 453

2) Synthesis of Intermediate 42

Intermediate 41 30g, 2,2-dimethyl-N-(2-methyl-5-(trimethylsilyl)phenyl)-2,3-dihydro-1H-inden-5-amine 21.5g was added to the synthesis method of intermediate 21 33 g of intermediate 42 was obtained using the same equivalent weight and conditions. (Yield 67%). MS[M+H]+ = 734

3) Synthesis of compound 18

In a nitrogen atmosphere, 8 g of intermediate 42 was added to 120 ml of toluene and then lowered to 0 ^O C, and then 25.5 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 5.5 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction was completed after the reaction was completed, 2.1 g of compound 18 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 27%). MS[M+H]+ = 713

Synthesis Example 19. Synthesis of Compound 19

1) Synthesis of Intermediate 43

2,2-dimethyl-N-(o-tolyl)-2,3-dihydro-1H-inden-5-amine 40g was used in the same amount and conditions as in the synthesis method of Intermediate No. 20 to obtain 45g of Intermediate 43. . (Yield 69%). MS[M+H]+ = 517

2) Synthesis of Intermediate 44

Intermediate 43 30g, 5-(tert-butyl)-N-(4-(trimethylsilyl)phenyl)-[1,1'-biphenyl]-2-amine 21.7g in the same amount and conditions as in the synthesis method of Intermediate No. 21 34 g of intermediate 44 was obtained by using. (Yield 69%). MS[M+H]+ = 854

3) Synthesis of compound 19

In a nitrogen atmosphere, 8 g of Intermediate 4 4 was added to 120 ml of toluene and then lowered to 0 ^O C, and then 22.1 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 1.8 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction after completion of the reaction, 2.2g of compound 19 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 28%). MS[M+H]+ = 828

Synthesis Example 20. Synthesis of Compound 20

1) Synthesis of Intermediate 45

N-(o-tolyl)-5,6,7,8-tetrahydronaphthalen-2-amine 40g was obtained using the same equivalent and conditions as in the synthesis method of Intermediate No. 20, 48g of intermediate 45 was obtained. (Yield 65%). MS[M+H]+ = 439

2) Synthesis of Intermediate 46

Intermediate 45 30g, N3-(o-tolyl)-N1-(p-tolyl)-N1-(4-(trimethylsilyl)phenyl)benzene-1,3-diamine 21.7g equivalent to the synthesis method of Intermediate No. 21 Using and conditions, 36g of intermediate 46 was obtained. (Yield 63%) MS[M+H]+ = 839

3) Synthesis of compound 20

In a nitrogen atmosphere, 8 g of intermediate 46 was added to 120 ml of toluene and then lowered to 0 ^O C, and then 22.5 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 1.9 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction after completion of the reaction, 2.3 g of compound 20 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 30%). MS[M+H]+ = 813

Synthesis Example 21. Synthesis of Compound 21

1) Synthesis of Intermediate 47

40 g of N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-5-amine as an intermediate Using the same equivalent weight and conditions as in Synthesis Method No. 25, 42 g of Intermediate 47 was obtained. (73% yield). MS[M+H]+ = 531

2) Synthesis of Intermediate 48

Intermediate 48 was prepared by using 30 g of Intermediate 47 and 17.7 g of 4-(tert-butyl)-2-methyl-N-(4-(trimethylsilyl)phenyl)aniline under nitrogen atmosphere in the same amount and conditions as in the synthesis method of Intermediate No. 26. 33g was obtained. (Yield 72%). MS[M+H]+ = 806

3) Synthesis of Intermediate 49

*

In a nitrogen atmosphere, 25 g of Intermediate 48 and 28 g of Intermediate 49 were obtained using the same equivalents and conditions as in the synthesis method of Intermediate No. 27. (Yield 83%). MS[M+H]+ = 1088

4) Synthesis of Intermediate 50

In a nitrogen atmosphere, 20 g of Intermediate 49 and 3.2 g of diphenylamine were used in the same amount and conditions as in the synthesis method No. 28 to obtain 13 g of Intermediate 50. (Yield 74%). MS[M+H]+ = 957

5) Synthesis of compound 21

In a nitrogen atmosphere, 8 g of intermediate 50 was added to 120 ml of toluene and then lowered to 0 ^O C, and 19.7 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 1.6 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After extraction after completion of the reaction, 1.9g of compound 21 was obtained through recrystallization after purification with an ethyl acetate:hexane column (yield 24%). MS[M+H]+ = 931

Synthesis Example 22. Synthesis of Compound 22

1) Synthesis of Intermediate 51

40 g of N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine was the same as the method for synthesizing intermediate No. 25 43g of intermediate 51 was obtained using equivalent weight and conditions. (Yield 74%). MS[M+H]+ = 517

2) Synthesis of Intermediate 52

In a nitrogen atmosphere, 30 g of intermediate 51 and 21.9 g of 4-(5-(tert-butyl)-2-methylphenyl)-4'-(trimethylsilyl)-[1,1'-biphenyl]-3-amine were added to intermediate 26. Using the same equivalent weight and conditions as in the synthesis method, 34 g of Intermediate 52 was obtained. (Yield 69%). MS[M+H]+ = 868

3) Synthesis of Intermediate 53

In a nitrogen atmosphere, 25 g of Intermediate 52 and 27 g of Intermediate 53 were obtained using the same equivalents and conditions as in the synthesis method of Intermediate No. 27. (Yield 82%). MS[M+H]+ = 1150

4) Synthesis of Intermediate 54

In a nitrogen atmosphere, 20 g of Intermediate 53 and 4.9 g of bis(4-(tert-butyl)phenyl)amine were used in the same amount and conditions as the synthesis method of Intermediate No. 28 to obtain 15 g of Intermediate 54. (Yield 76%). MS[M+H]+ = 1132

5) Synthesis of compound 22

In a nitrogen atmosphere, 8 g of intermediate 54 was added to 120 ml of toluene and then lowered to 0 ^O C, and 16.7 ml of Tert-butyllithium (1.7M) was slowly added dropwise. After 1 hour, 1.4 ml of boron tribromide was added dropwise and then raised to 60 ^O C and stirred for 12 hours. After completion of the reaction, extraction, purification with an ethyl acetate:hexane column, followed by recrystallization to give 2.1 g of compound 22 (yield 27%). MS[M+H]+ = 1105

<Experimental Example>

<Example 1>

A glass substrate coated with a thin film of 1,500Å of indium tin oxide (ITO) was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode prepared as described above, the following formula [HAT] was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer. A hole transport layer was formed by vacuum depositing the following formula [NPB] to a thickness of 1100Å on the hole injection layer. The electron suppressing layer was formed by vacuum depositing the following formula [HT-A] to a thickness of 200 Å on the hole transport layer. Subsequently, 2 wt% of Compound 1 as a blue light emitting dopant as a blue light emitting dopant on the electron-suppressing layer, and 2-(10-phenylanthracene-9-yl)dibenzo[b,d]furan[BH] as a host having a thickness of 300 Å A light emitting layer was formed by vacuum evaporation. On the light emitting layer, [TPBI] and the following formula [LiQ] were vacuum-deposited at a 1:1 weight ratio to form a first electron transport layer to a thickness of 200Å. [LiF] was vacuum deposited on the first electron transport layer to form a second electron transport layer with a thickness of 100 Å. A cathode was formed by depositing aluminum to a thickness of 1,000 Å on the second electron transport layer. In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.9 Å/sec, the lithium fluoride of the second electron transport layer was 0.3 Å/sec, and the deposition rate of the aluminum of the cathode was maintained at 2 Å/sec. The degree of vacuum was maintained at 1 Х 10 ^-7 ~ 5 Х 10 ^-8 torr, thereby fabricating an organic light emitting device.

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Examples 1-1 to 1-22 and Comparative Examples 1 to 3.

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound of Table 1 below was used instead of Compound 1 in Example 1-1. In the above, the efficiency, lifetime, and color coordinates (based on 1931 CIE color coordinates) of the organic light emitting devices manufactured in Examples 1-1 to 1-22 and Comparative Examples 1 to 3 at a current density of 10 mA/cm 2 were measured, The results are shown in Table 1 below.

compound Efficiency (cd/A) Color coordinates life span CIE (x) CIE (y) T95(hr) Example 1-1 Compound 1 7.4 0.133 0.053 240 Example 1-2 Compound 2 8.1 0.166 0.195 266 Example 1-3 Compound 3 7.5 0.138 0.055 241 Example 1-4 Compound 4 7.5 0.133 0.056 243 Example 1-5 Compound 5 7.4 0.134 0.051 239 Example 1-6 Compound 6 7.9 0.135 0.052 241 Example 1-7 Compound 7 7.8 0.133 0.051 243 Example 1-8 Compound 8 7.9 0.132 0.051 241 Example 1-9 Compound 9 7.9 0.133 0.051 245 Example 1-10 Compound 10 8.2 0.134 0.052 239 Example 1-11 Compound 11 8.4 0.135 0.112 245 Example 1-12 Compound 12 8.5 0.137 0.114 262 Example 1-13 Compound 13 8.3 0.138 0.053 241 Example 1-14 Compound 14 8.5 0.141 0.051 238 Example 1-15 Compound 15 8.7 0.143 0.11 266 Example 1-16 Compound 16 8.6 0.142 0.051 245 Example 1-17 Compound 17 8.8 0.134 0.052 249 Example 1-18 Compound 18 7.6 0.141 0.051 245 Example 1-19 Compound 19 7.3 0.142 0.051 244 Example 1-20 Compound 20 8.2 0.143 0.05 243 Example 1-21 Compound 21 8.3 0.145 0.051 244 Example 1-22 Compound 22 8.3 0.143 0.111 265 Comparative Example 1 Comparative compound 1 6 0.141 0.051 190 Comparative Example 2 Comparative compound 2 6.2 0.135 0.11 222 Comparative Example 3 Comparative compound 3 6.4 0.161 0.199 229

<Comparative Examples 4 and 5 and Examples 2-1 to 2-4>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound of Table 2 below was used instead of Compound 1 in Example 1-1. In the above, the efficiency, lifespan, and color coordinates (based on 1931 CIE color coordinates) of the organic light-emitting devices manufactured in Comparative Examples 4 and 5 and Examples 2-1 to 2-4 at a current density of 10 mA/cm2 were determined by temperature (room temperature). / 50 ^o C /60 ^o C ), and the results are shown in Table 2 below.

compound Room temperature 50 ^o C 60 ^o C Efficiency (cd/A) Life T(95h) Efficiency (cd/A) Life T(95h) Efficiency (cd/A) Life T(95h) Comparative Example 4 Comparative compound 2 6.2 222 5.4 200 4.3 155 Comparative Example 5 Comparative compound 3 6.4 229 6.2 190 5.8 160 Example 2-1 Compound 2 8.1 266 8.1 265 8 263 Example 2-2 Compound 6 7.9 241 7.8 240 7.6 235 Example 2-3 Compound 9 7.9 245 7.8 244 7.5 240 Example 2-4 Compound 15 8.7 266 8.7 265 8.5 262

*From Table 1 above, Examples 1-1 to 1-22 using the compound of the present invention containing a hydrocarbon ring in the molecule are substituted with an alicyclic hydrocarbon ring in Comparative Examples 1 to 2 and R1 using a compound without an alicyclic hydrocarbon ring It can be seen that the efficiency and life characteristics are very superior to those of Comparative Example 3. When the alicyclic hydrocarbon ring is condensed in the core of the compound, the distance between molecules is increased, and the efficiency is increased by suppressing collisions between singlet electrons-singlet electrons and singlet electrons-polaron electrons.

In addition, it can be confirmed that even if a phenomenon in which the hydrocarbon ring is broken by heat or light occurs, it is stabilized without affecting the wavelength that emits light, thus showing a high lifespan. This is supported in Comparative Examples 4 and 5 and Examples 2-1 to 2-4. In the case of Examples 2-1 to 2-4 using the compound in which the alicyclic hydrocarbon ring is condensed in the core, it can be seen that the efficiency and life characteristics are remarkably improved as compared to Comparative Examples 4 and 5 which are not.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: electron suppression layer
8: first electron transport layer
9: second electron transport layer

Claims (16)

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

In Formula 1,
Cy1 to Cy4 are the same as or different from each other, and each independently one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, and heterocyclic group, or from the group Benzene substituted or unsubstituted with a substituent linked by two or more selected groups; Or one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, and heterocyclic group, or substituted or unsubstituted with a substituent to which two or more groups selected from the group are linked It is a condensed hydrocarbon ring of two or more rings including an alicyclic hydrocarbon ring,
At least one of Cy1 to Cy4 is one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, and heterocyclic group, or a substituent connected with two or more groups selected from the group It is a condensed hydrocarbon ring of two or more rings substituted or unsubstituted with and including an alicyclic hydrocarbon ring,
R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A silyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group and an aryl group, or a substituent connected with two or more groups selected from the group; Alkyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, and heterocyclic group or a substituent to which two or more groups selected from the group are connected ; Cycloalkyl group; Substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, heterocyclic group and condensed hydrocarbon ring group, or a substituent connected with two or more groups selected from the group; or Unsubstituted aryl group; Substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, heterocyclic group and condensed hydrocarbon ring group, or a substituent connected with two or more groups selected from the group; or Unsubstituted amine group; Condensation unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, and heterocyclic group or a substituent connected with two or more groups selected from the group Hydrocarbon ring group; Or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, heterocyclic group and condensed hydrocarbon ring group, or a substituent connected with two or more groups selected from the group. Or an unsubstituted heterocyclic group,
n1 is an integer of 0 to 3, and when n1 is 2 or more, 2 or more R1s are the same as or different from each other,
The alkyl group has 1 to 10 carbon atoms, the cycloalkyl group has 3 to 30 carbon atoms, the alicyclic hydrocarbon ring has 3 to 30 carbon atoms, the aryl group has 6 to 30 carbon atoms, and the heterocyclic group The number of carbon atoms is 2 to 30, the heterocyclic group includes at least one of N, O, S and Si as a hetero atom, and the number of carbon atoms of the condensed hydrocarbon ring and the condensed hydrocarbon ring group is 9 to 60. delete The method according to claim 1,
Formula 1 is a compound represented by any one of the following Formulas 2 to 4:
[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,
R1 and n1 are as defined in Formula 1,
Y1 to Y4; And Y5 to Y8 are bonded to each other to each of at least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, a cycloalkyl group, an amine group, an aryl group, and a heterocyclic group, or two or more groups selected from the group. Forming a substituted or unsubstituted aromatic hydrocarbon ring with a connected substituent,
X1 and X2; X3 and X4; X5 and X6; And at least one selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, and heterocyclic group by bonding with each other at least two selected from the group consisting of X7 and X8, or To form a substituted or unsubstituted alicyclic hydrocarbon ring with a substituent connected to two or more groups selected from the group,
Z1 to Z3; Z4 to Z6; Z7 to Z9; And at least one selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, a cycloalkyl group, an amine group, an aryl group, and a heterocyclic group by bonding with each other at least two selected from the group consisting of Z10 to Z12, or To form a condensed ring of an aromatic hydrocarbon ring and an alicyclic hydrocarbon ring substituted or unsubstituted with a substituent connected to two or more groups selected from the group,
Z1 to Z3; Z4 to Z6; Z7 to Z9; And at least one of the rings formed by bonding of two or more selected from the group consisting of Z10 to Z12 with each other is an alicyclic hydrocarbon ring,
R2 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A silyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group and an aryl group, or a substituent connected with two or more groups selected from the group; Alkyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, and heterocyclic group or a substituent to which two or more groups selected from the group are connected ; Cycloalkyl group; Substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, heterocyclic group and condensed hydrocarbon ring group, or a substituent connected with two or more groups selected from the group; or Unsubstituted amine group; Substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, heterocyclic group and condensed hydrocarbon ring group, or a substituent connected with two or more groups selected from the group; or Unsubstituted aryl group; Condensation unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, and heterocyclic group or a substituent connected with two or more groups selected from the group Hydrocarbon ring group; Or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, heterocyclic group and condensed hydrocarbon ring group, or a substituent connected with two or more groups selected from the group. Or an unsubstituted heterocyclic group,
n6, n7, n12 and n13 are each an integer of 0 to 2, and when n6, n7, n12 and n13 are each 2, the substituents in the two parentheses are the same or different from each other,
n4 and n5 are each an integer of 0 to 7,
n8 and n9 are each an integer of 0 to 3,
n2 and n3 are each an integer of 0 to 4,
When n2, n3, n4, n5, n8 and n9 are each 2 or more, the substituents in the plurality of parentheses are the same or different from each other,
The number of carbon atoms of the alkyl group is 1 to 10, the number of carbon atoms of the cycloalkyl group is 3 to 30, the number of carbon atoms of the alicyclic hydrocarbon ring is 3 to 30, the number of carbon atoms of the aryl group and the aromatic hydrocarbon ring is 6 to 30, the The number of carbon atoms of the heterocyclic group is 2 to 30, the heterocyclic group includes one or more of N, O, S, and Si as a hetero atom, and the number of carbon atoms of the condensed hydrocarbon ring group is 9 to 60. The method of claim 3,
Formula 2 is a compound represented by the following Formula 5:
[Formula 5]

In Formula 5,
R1 to R5 and n1 to n5 are as defined in Formula 2,
Cy11 and Cy12 are the same as or different from each other, and each independently one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, heterocyclic group and condensed hydrocarbon ring group Or an aromatic hydrocarbon ring unsubstituted or substituted with a substituent to which two or more groups selected from the group are connected,
The number of carbon atoms of the alkyl group is 1 to 10, the number of carbon atoms of the cycloalkyl group is 3 to 30, the number of carbon atoms of the aryl group and the aromatic hydrocarbon ring is 6 to 30, the number of carbon atoms of the heterocyclic group is 2 to 30, and the hetero The cyclic group includes at least one of N, O, S and Si as a hetero atom, and the number of carbon atoms of the condensed hydrocarbon cyclic group is 9 to 60. The method of claim 3,
Formula 3 is a compound represented by any one of Formulas 6 to 8 below:
[Formula 6]

[Formula 7]

[Formula 8]

In Formulas 6 to 8,
R1, R6 to R9, n1 and n6 to n9 are as defined in Formula 3,
Cy13 to Cy16 are the same as or different from each other, and each independently one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, and heterocyclic group, or It is a substituted or unsubstituted alicyclic hydrocarbon ring with a substituent to which two or more selected groups are connected,
The alkyl group has 1 to 10 carbon atoms, the cycloalkyl group has 3 to 30 carbon atoms, the alicyclic hydrocarbon ring has 3 to 30 carbon atoms, the aryl group has 6 to 30 carbon atoms, and the heterocyclic group The number of carbon atoms is 2 to 30, and the heterocyclic group includes at least one of N, O, S and Si as a hetero atom. The method of claim 3,
Formula 4 is a compound represented by the following Formula 9 or Formula 10:
[Formula 9]

[Formula 10]

In Formulas 9 and 10,
R1, R10, R11 to R13, n1, n12 and n13 are as defined in Formula 4,
R14 to R17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A silyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group and an aryl group, or a substituent connected with two or more groups selected from the group; Alkyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, and heterocyclic group or a substituent to which two or more groups selected from the group are connected ; Cycloalkyl group; Substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, heterocyclic group and condensed hydrocarbon ring group, or a substituent connected with two or more groups selected from the group; or Unsubstituted aryl group; Condensation unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, and heterocyclic group or a substituent connected with two or more groups selected from the group Hydrocarbon ring group; Or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, heterocyclic group and condensed hydrocarbon ring group, or a substituent connected with two or more groups selected from the group. Or an unsubstituted heterocyclic group,
n14 and n15 are each an integer of 0 to 4, n16 and n17 are each an integer of 0 to 5, and when n14 to n17 are each 2 or more, the substituents in a plurality of parentheses are the same or different from each other,
p1 to p4 are each 1 or 2,
The number of carbon atoms of the alkyl group is 1 to 10, the number of carbon atoms of the cycloalkyl group is 3 to 30, the number of carbon atoms of the aryl group is 6 to 30, the number of carbon atoms of the heterocyclic group is 2 to 30, and the heterocyclic group is a heteroatom. At least one of N, O, S, and Si is included, and the number of carbon atoms of the condensed hydrocarbon ring group is 9 to 60. A compound represented by any one of the following compounds:

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 and 3 to 7 Light-emitting element. The method of claim 8,
The organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound. The method of claim 8,
The organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound. The method of claim 8,
The organic material layer includes an emission layer, and the emission layer includes the compound. The method of claim 8,
The organic material layer includes an emission layer, and the emission layer includes the compound as a dopant of the emission layer. The method according to claim 1,
At least one of the alicyclic hydrocarbon rings contained in the Cy1 to Cy4 is
A compound containing an alkyl group having 1 to 10 carbon atoms as a substituent. The method of claim 3,
Formula 1 is represented by Formula 3 or 4,
R8, R9, R12 and R13 are the same as or different from each other, and each independently a halogen group; Cyano group; A silyl group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group or a substituent connected with two or more groups selected from the group; Alkyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, and heterocyclic group or a substituent to which two or more groups selected from the group are connected ; Cycloalkyl group; Substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, heterocyclic group and condensed hydrocarbon ring group, or a substituent connected with two or more groups selected from the group; or Unsubstituted amine group; Substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, heterocyclic group and condensed hydrocarbon ring group, or a substituent connected with two or more groups selected from the group; or Unsubstituted aryl group; Condensation unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, and heterocyclic group or a substituent connected with two or more groups selected from the group Hydrocarbon ring group; Or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, heterocyclic group and condensed hydrocarbon ring group, or a substituent connected with two or more groups selected from the group. Or an unsubstituted heterocyclic group,
At least one of R8 and R9; And at least one of R12 and R13 is connected to the ortho position with respect to nitrogen (N),
n8+n9 is 1 or more, n12+n13 is 1 or more,
The number of carbon atoms of the alkyl group is 1 to 10, the number of carbon atoms of the cycloalkyl group is 3 to 30, the number of carbon atoms of the aryl group is 6 to 30, the number of carbon atoms of the heterocyclic group is 2 to 30, and the heterocyclic group is a heteroatom. A compound comprising at least one of N, O, S, and Si, and the number of carbon atoms of the condensed hydrocarbon ring group is 9 to 60. The method of claim 3,
Formula 1 is represented by Formula 3 or 4,
X5 and X6; And at least one selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, cycloalkyl group, amine group, aryl group, and heterocyclic group by bonding with each other at least two selected from the group consisting of X7 and X8, or To form a substituted or unsubstituted alicyclic hydrocarbon ring with a substituent connected to two or more groups selected from the group,
Z7 to Z9; And at least one selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, a cycloalkyl group, an amine group, an aryl group, and a heterocyclic group by bonding with each other at least two selected from the group consisting of Z10 to Z12, or To form a condensed ring of an aromatic hydrocarbon ring and an alicyclic hydrocarbon ring substituted or unsubstituted with a substituent connected to two or more groups selected from the group,
At least one of the alicyclic hydrocarbon ring and the aromatic hydrocarbon ring is condensed at the ortho position and meta position with respect to nitrogen (N),
The number of carbon atoms of the alkyl group is 1 to 10, the number of carbon atoms of the cycloalkyl group is 3 to 30, the number of carbon atoms of the alicyclic hydrocarbon ring is 3 to 30, the number of carbon atoms of the aryl group and the aromatic hydrocarbon ring is 6 to 30, the The number of carbon atoms of the heterocyclic group is 2 to 30, and the heterocyclic group is a compound containing at least one of N, O, S and Si as a hetero atom. The method of claim 3,
Formula 1 is a compound represented by Formula 2.

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