KR20230108721A - Compound and organic light emitting device comprising same - Google Patents

Abstract

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

Description

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0003736 filed with the Korean Intellectual Property Office on January 11, 2022, the entire contents of which are incorporated herein.

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

In this specification, an organic light emitting device is a light emitting device using an organic semiconductor material, and requires exchange of holes and/or electrons between an electrode and an organic semiconductor material. The organic light emitting device can be roughly divided into two types according to the operation principle as follows. First, excitons are formed in the organic material layer by photons introduced into the device from an external light source, and these 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 light emitting device of the form. The second is a type of light emitting device that injects holes and/or electrons into the organic semiconductor material layer forming the interface with the electrodes by applying voltage or current to two or more electrodes and operates by the injected electrons and holes.

In general, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, and an electron injection layer. can lose In the structure of this 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 when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows. Such an organic light emitting device is known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.

Materials used as the organic 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, and electron injection materials, depending on their functions. Light-emitting materials include blue, green, and red light-emitting materials according to light-emitting colors, and yellow and orange light-emitting materials required to realize better natural colors.

In addition, in order to increase color purity and increase light emitting 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 a smaller energy band gap and higher luminous efficiency than the host constituting the light emitting layer is mixed in the light emitting layer in a small amount, excitons generated in the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength range of the dopant, light of 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 constituting 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. Supported by this, the development of new materials is continuously required.

International Patent Publication No. 2017-126443

In this 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,

R2 and R3 are the same as or different from each other, and are each independently hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted An arylalkyl group, a substituted or unsubstituted arylalkenyl group, or a substituted or unsubstituted heteroaryl group,

R4 and R5 combine with each other to form a substituted or unsubstituted hydrocarbon ring,

Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl group. A heteroaryl group or a hydrocarbon ring group in which a substituted or unsubstituted aliphatic ring and an aromatic ring are condensed,

L, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted divalent alkoxy group, a substituted or unsubstituted divalent arylalkenyl group, a substituted or unsubstituted divalent arylalkenyl group, A cyclic arylene group, or a substituted or unsubstituted heteroarylene group,

R1 is Formula 2;

[Formula 2]

　

In Formula 2, the dotted line is a site that binds to L,

R6 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group;

m is an integer from 0 to 3, and when m is 2 or more, R2 is the same as or different from each other;

n is an integer from 0 to 3, and when n is 2 or more, R3 is the same as or different from each other;

l is an integer from 0 to 11, and when l is 2 or more, R6 is the same as or different from each other.

In addition, 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 layer 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 lifespan can be obtained, and the compound of the present invention can be used as a hole injection layer, a hole transport layer, or an electron suppression layer of an organic light emitting device. When included in the layer, an organic light emitting device having characteristics of low voltage, high efficiency, and long lifespan can be manufactured.

In particular, Formula 2 is bonded to the 7-position of fluorene and amine is connected to the 2-position, thereby adjusting the HOMO and LUMO energy levels of the compound, thereby adjusting the energy barrier with the organic material layer.

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.

In the present specification, when a certain component is said to "include", it means that it may further include other components without excluding other components unless otherwise stated.

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

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

In this specification, the term "substituted or unsubstituted" means 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, which is substituted with one or two or more substituents selected from the group consisting of two or more substituents among the substituents exemplified above, or a substituent in which two or more substituents are connected. For example, "a substituent in 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 in 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 a chemical formula of -SiY1Y2Y3, wherein Y1, Y2 and Y3 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, and the like, but is not limited thereto. don't

In the present specification, the boron group may be represented by a chemical formula of -BY4Y5, wherein Y4 and Y5 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, a phenyl boron group, but is not limited thereto.

In the present specification, the alkyl group may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. 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, and an octyl group.

In the present specification, the arylalkyl group refers to an alkyl group substituted with an aryl group. The number of carbon atoms is not particularly limited, but according to an exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 30, and the number of carbon atoms of the aryl group substituted with the alkyl group is 6 to 30.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-alkyl arylamine 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 a methylamine group; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; naphthylamine group; Biphenylamine group; an anthracenylamine group; 9-methylanthracenylamine group; diphenylamine group; ditolylamine group; N-phenyltolylamine group; triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenyl naphthylamine 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 means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.

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

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

In the present specification, the alkyl group of an alkylamine group, an N-arylalkylamine group, an alkylthioxy group, an alkylsulfoxy group, and an N-alkylheteroarylamine group is the same as the above-mentioned alkyl group. Specifically, the alkylthioxy group includes a methylthioxyl group; Ethylthioxy group; tert-butyl thioxy group; Hexylthioxy group; and octylthioxy group, and the alkyl sulfoxy group includes mesyl; ethyl sulfoxy group; propyl sulfoxy group; Butyl sulfoxy group and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 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 number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. 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 are not limited thereto.

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

In the present specification, the heteroaryl group is a ring group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. According to one embodiment, the carbon number 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, a carbazole group, and the like. However, it is not limited to these.

In the present specification, the meaning of “adjacent” in “forming a ring by bonding with adjacent groups” is the same as described above, and the “ring” refers to a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring.

In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, except for the non-monovalent cycloalkyl group, aryl group, and combinations thereof It may be selected from examples, and the hydrocarbon ring may be benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2, 3,4-tetrahydro-1,4-methanonaphthalene, and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene, but are not limited thereto.

In this specification, a hydrocarbon ring is a generic term for a ring composed of carbon and hydrogen. Types of the hydrocarbon ring include, but are not limited to, an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, or a hydrocarbon ring in which aliphatic and aromatic rings are condensed with each other.

In the present specification, the aromatic hydrocarbon ring has the same definition as the aryl group except that it is not monovalent.

In the present specification, the aliphatic hydrocarbon ring includes both a hydrocarbon ring with a single bond, a hydrocarbon ring with multiple bonds, or a condensed ring with a single bond and a multiple bond. Therefore, a ring consisting of a single bond in an aliphatic hydrocarbon ring includes the cycloalkyl group. Hydrocarbon rings that contain single bonds and double bonds, such as cyclohexene, but are not aromatic rings, also belong to aliphatic hydrocarbon rings.

Unless defined otherwise herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein may be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patent applications, patents and other references mentioned herein are hereby incorporated by reference in their entirety, and in case of conflict, the present specification, including definitions, will control unless a specific passage is stated. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.

In the present specification, the arylene group is the same as defined in the above aryl group except that it is a divalent group.

In the present specification, the heteroarylene group is the same as defined in the above heteroaryl group, except that it is a divalent group.

According to an exemplary embodiment of the present specification, Formula 1 is Formula 1-1 or Formula 1-2 below.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

The definitions of R2 to R6, L, L1, L2, Ar1, Ar2, n, m, and l are as defined in Formulas 1 and 2 above.

According to an exemplary embodiment of the present specification, R4 and R5 combine with each other to form a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R4 and R5 combine with each other to form a substituted or unsubstituted hydrocarbon ring having 3 to 25 carbon atoms.

According to an exemplary embodiment of the present specification, R4 and R5 combine with each other to form a substituted or unsubstituted hydrocarbon ring having 3 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R4 and R5 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a condensed ring thereof. form

According to an exemplary embodiment of the present specification, R4 and R5 combine with each other to form a substituted or unsubstituted cycloalkyl ring having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R4 and R5 combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R4 and R5 are bonded to each other to form a condensed ring of a substituted or unsubstituted cycloalkyl ring having 3 to 30 carbon atoms and a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms. form

According to an exemplary embodiment of the present specification, R4 and R5 combine with each other to form a substituted or unsubstituted fluorene ring.

According to an exemplary embodiment of the present specification, R4 and R5 combine with each other to form an unsubstituted fluorene ring.

According to an exemplary embodiment of the present specification, R6 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R6 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

According to an exemplary embodiment of the present specification, R6 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

According to an exemplary embodiment of the present specification, R6 is hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R6 is hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms.

According to an exemplary embodiment of the present specification, R6 is hydrogen, deuterium, or an alkyl group having 1 to 4 carbon atoms.

According to an exemplary embodiment of the present specification, R6 is hydrogen, heavy hydrogen, a methyl group, an ethyl group, an isopropyl group, a propyl group, a butyl group, a terbutyl group, a pentyl group, or a hexyl group.

According to an exemplary embodiment of the present specification, R6 is hydrogen, a methyl group, an ethyl group, an isopropyl group, a propyl group, a butyl group, a terbutyl group, a pentyl group, or a hexyl group.

According to an exemplary embodiment of the present specification, R6 is hydrogen, deuterium, a methyl group, or an ethyl group.

According to an exemplary embodiment of the present specification, R6 is hydrogen, deuterium, or a methyl group.

According to an exemplary embodiment of the present specification, Formula 2 has the following structure.

The dotted line is a site that binds to L.

According to an exemplary embodiment of the present specification, Formula 1 is any one of Formulas 1-3 or 1-4 below.

[Formula 1-3]

[Formula 1-4]

In Formulas 1-3 and 1-4, R2, R3, R6, L, L1, L2, Ar1, Ar2, l, m and n are as defined in Formulas 1 and 2 above.

According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted group. It is a heteroaryl group.

According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted carbon atom having 6 to 10 carbon atoms. It is an aryl group of 30, or a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted carbon atom having 6 to 10 carbon atoms. It is an aryl group of 20, or a substituted or unsubstituted heteroaryl group of 3 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted carbon atom having 6 to 10 carbon atoms. It is an aryl group of 15, or a substituted or unsubstituted heteroaryl group of 3 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a carbon number 3 to 30 It is a heteroaryl group of

According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a carbon number 3 to 20 It is a heteroaryl group of

According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a carbon number 3 to 15 It is a heteroaryl group of

According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represent hydrogen, deuterium, or a methyl group.

According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represent hydrogen or deuterium.

According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represent hydrogen or deuterium.

According to an exemplary embodiment of the present specification, R2 is hydrogen.

According to an exemplary embodiment of the present specification, R2 is deuterium.

According to an exemplary embodiment of the present specification, R3 is hydrogen.

According to an exemplary embodiment of the present specification, R3 is deuterium.

According to an exemplary embodiment of the present specification, R2 is hydrogen, and R3 is deuterium.

According to an exemplary embodiment of the present specification, R2 is deuterium, and R3 is hydrogen.

According to an exemplary embodiment of the present specification, R2 and R3 are hydrogen.

According to an exemplary embodiment of the present specification, R2 and R3 are deuterium.

According to an exemplary embodiment of the present specification, R6 is hydrogen.

According to an exemplary embodiment of the present specification, R6 is deuterium.

According to an exemplary embodiment of the present specification, at least one of R6 is deuterium.

According to an exemplary embodiment of the present specification, two or more of R6 are deuterium.

According to an exemplary embodiment of the present specification, 3 or more of R6 are deuterium.

According to an exemplary embodiment of the present specification, 4 or more of R6 are deuterium.

According to an exemplary embodiment of the present specification, 5 or more of R6 are deuterium.

According to an exemplary embodiment of the present specification, 6 or more of R6 are deuterium.

According to an exemplary embodiment of the present specification, 7 or more of R6 are deuterium.

According to an exemplary embodiment of the present specification, 8 or more of R6 are deuterium.

According to an exemplary embodiment of the present specification, 9 or more of R6 are deuterium.

According to an exemplary embodiment of the present specification, 10 or more of R6 are deuterium.

According to an exemplary embodiment of the present specification, L, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted carbon number 3 to 30 It is a heteroarylene group of 30.

According to an exemplary embodiment of the present specification, L, L1 and L2 are the same as or different from each other, and are each independently a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L is a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L is a direct bond, a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.

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

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a deuterium-substituted arylene group having 6 to 30 carbon atoms, or a deuterium-substituted heteroaryl group having 3 to 30 carbon atoms it's rengi

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a deuterium-substituted arylene group having 6 to 20 carbon atoms, or a deuterium-substituted heteroaryl group having 3 to 20 carbon atoms it's rengi

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 3 to 30 carbon atoms. It is a heteroarylene group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond or an arylene group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond or an arylene group having 6 to 20 carbon atoms substituted with deuterium.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond or an arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted with deuterium, a divalent biphenyl group substituted or unsubstituted with deuterium, or a deuterium substituted or unsubstituted biphenyl group. Substituted or unsubstituted divalent naphthyl group, divalent terphenyl group substituted or unsubstituted with deuterium, divalent anthracene group substituted or unsubstituted with deuterium, divalent phenanthrene group substituted or unsubstituted with deuterium, divalent phenanthrene group substituted with deuterium Or an unsubstituted divalent furan group, a divalent thiophene group unsubstituted or substituted with deuterium, a divalent pyrrole group unsubstituted or substituted with deuterium, a divalent pyrimidine group substituted or unsubstituted with deuterium, a deuterium substituted Or an unsubstituted divalent pyridine group, a deuterium-substituted or unsubstituted divalent triazine, a deuterium-substituted or unsubstituted divalent dibenzofuran group, a deuterium-substituted or unsubstituted divalent dibenzothiophene group, A divalent carbazole group unsubstituted or substituted with deuterium, a divalent quinoline group unsubstituted or substituted with deuterium, a divalent quinazoline group unsubstituted or substituted with deuterium, a divalent quinoxaline group unsubstituted or substituted with deuterium, A divalent benzoxazole group unsubstituted or substituted with deuterium, or a divalent benzothiazole group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted with deuterium, a divalent biphenyl group substituted or unsubstituted with deuterium, or a deuterium It is a divalent naphthyl group substituted or unsubstituted with

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, a divalent terphenyl group, a divalent anthracene group, a divalent Divalent phenanthrene group, divalent furan group, divalent thiophene group, divalent pyrrole group, divalent pyrimidine group, divalent pyridine group, divalent triazine, divalent dibenzofuran group, divalent dibenzothiophene group, a divalent carbazole group, a divalent quinoline group, a divalent quinazoline group, a divalent quinoxaline group, a divalent benzoxazole group, or a divalent benzothiazole group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond, a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond, a phenylene group, or a divalent biphenyl group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond, a phenylene group, or a divalent naphthyl group.

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

According to one embodiment of the present specification, L1 is a direct bond.

According to one embodiment of the present specification, L2 is a direct bond.

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

According to an exemplary embodiment of the present specification, L1 is a phenylene group.

According to one embodiment of the present specification, L2 is a phenylene group.

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

According to an exemplary embodiment of the present specification, L1 is a divalent biphenyl group.

According to an exemplary embodiment of the present specification, L2 is a divalent biphenyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, It is an unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a hydrocarbon ring group in which a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring are condensed.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, It is an unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a hydrocarbon ring group in which a substituted or unsubstituted aliphatic ring having 3 to 20 carbon atoms and an aromatic ring are condensed.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, It is an unsubstituted heteroaryl group having 3 to 15 carbon atoms, or a hydrocarbon ring group in which a substituted or unsubstituted aliphatic ring having 3 to 15 carbon atoms and an aromatic ring are condensed.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium, a deuterium number or an alkyl group having 6 to 6 carbon atoms substituted or unsubstituted with an alkyl group It is an aryl group of 20, a heteroaryl group having 3 to 20 carbon atoms substituted or unsubstituted with heavy hydrogen, or a hydrocarbon ring group in which an aliphatic ring and an aromatic ring substituted or unsubstituted with 3 to 20 carbon atoms are condensed.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently deuterium, an alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium, an alkyl group, or a cycloalkyl group; A heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; or a hydrocarbon ring group in which an aliphatic ring having 3 to 30 carbon atoms unsubstituted or substituted with a deuterium or alkyl group and an aromatic ring are condensed.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with a deuterium, alkyl group, or cycloalkyl group; a heteroaryl group having 3 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen; or a hydrocarbon ring group in which an aliphatic ring having 3 to 20 carbon atoms unsubstituted or substituted with a deuterium or alkyl group is condensed with an aromatic ring.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 15 carbon atoms unsubstituted or substituted with a deuterium, an alkyl group, or a cycloalkyl group; a heteroaryl group having 3 to 15 carbon atoms unsubstituted or substituted with heavy hydrogen; or a condensed hydrocarbon ring group of heavy hydrogen or an aliphatic ring having 3 to 15 carbon atoms and an aromatic ring.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with deuterium, an alkyl group, or a cycloalkyl group; A biphenyl group unsubstituted or substituted with deuterium, an alkyl group, or a cycloalkyl group; Naphthyl group unsubstituted or substituted with heavy hydrogen, an alkyl group, or a cycloalkyl group; A terphenyl group unsubstituted or substituted with heavy hydrogen, an alkyl group, or a cycloalkyl group; An anthracene group unsubstituted or substituted with heavy hydrogen; A phenanthrene group unsubstituted or substituted with deuterium, an alkyl group, or a cycloalkyl group; A triphenylene group unsubstituted or substituted with heavy hydrogen; A fluorene group substituted with heavy hydrogen, an alkyl group or a phenyl group; Dibenzofuran group; Dibenzothiophene group; carbazole group; or a tetrahydronaphthalene group substituted with an alkyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; A naphthyl group unsubstituted or substituted with heavy hydrogen; A terphenyl group unsubstituted or substituted with heavy hydrogen; An anthracene group unsubstituted or substituted with heavy hydrogen; A phenanthrene group unsubstituted or substituted with heavy hydrogen; A triphenylene group unsubstituted or substituted with heavy hydrogen; A fluorene group unsubstituted or substituted with deuterium or an alkyl group; A dibenzofuran group unsubstituted or substituted with heavy hydrogen; A dibenzothiophene group unsubstituted or substituted with heavy hydrogen; A carbazole group unsubstituted or substituted with heavy hydrogen; Or a tetrahydronaphthalene group unsubstituted or substituted with deuterium or an alkyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as each other, a phenyl group; biphenyl group; naphthyl group; terphenyl group; anthracene group; phenanthrene group; triphenylene group; dimethyl fluorene group; Dibenzofuran group; Dibenzothiophene group; carbazole group; Or a tetramethyltetrahydronaphthalene group,

The substituents are unsubstituted or substituted with deuterium, methyl, ethyl, terbutyl, or adamantyl groups.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are different from each other, and each independently a phenyl group; biphenyl group; naphthyl group; terphenyl group; anthracene group; phenanthrene group; triphenylene group; dimethyl fluorene group; Dibenzofuran group; Dibenzothiophene group; carbazole group; Or a tetramethyltetrahydronaphthalene group,

The substituents are unsubstituted or substituted with deuterium, methyl, ethyl, terbutyl, or adamantyl groups.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are different from each other, and each independently an adamantyl group; phenyl group; biphenyl group; naphthyl group; terphenyl group; anthracene group; phenanthrene group; triphenylene group; fluorene group; Dibenzofuran group; Dibenzothiophene group; carbazole group; Or a tetramethyltetrahydronaphthalene group,

the adamantyl group; phenyl group; biphenyl group; naphthyl group; terphenyl group; anthracene group; phenanthrene group; triphenylene group; fluorene group; Dibenzofuran group; Dibenzothiophene group; carbazole group; or tetramethyltetrahydronaphthalene is independently substituted or unsubstituted with deuterium, a methyl group, an ethyl group, a terbutyl group, or a phenyl group.

According to an exemplary embodiment of the present specification, one of Ar1 and Ar2 is a hydrocarbon ring group in which a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring are condensed.

According to an exemplary embodiment of the present specification, one of Ar1 and Ar2 is a hydrocarbon ring group condensed with an aliphatic ring having 3 to 30 carbon atoms and an aromatic ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, one of Ar1 and Ar2 is tetrahydronaphthalene unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, one of Ar1 and Ar2 is a tetrahydronaphthalene group unsubstituted or substituted with a methyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted hydrocarbon ring group in which an aliphatic ring having 3 to 30 carbon atoms and an aromatic ring are condensed.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a condensed hydrocarbon ring of an aliphatic ring having 3 to 30 carbon atoms and an aromatic ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms. It is Ki.

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

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a tetrahydronaphthalene group unsubstituted or substituted with a methyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; biphenyl group; naphthyl group; terphenyl group; anthracene group; phenanthrene group; triphenylene group; or a dimethylfluorene group.

According to an exemplary embodiment of the present specification, Ar1 is an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, and Ar2 is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, and Ar2 is a substituted or unsubstituted aryl group having 3 to 20 carbon atoms unsubstituted or substituted with deuterium. 20 is a heteroaryl group.

According to an exemplary embodiment of the present specification, Ar1 is a phenyl group; biphenyl group; naphthyl group; terphenyl group; anthracene group; phenanthrene group; triphenylene group; Or a dimethylfluorene group, Ar2 is a dibenzofuran group; Dibenzothiophene group; or a carbazole group.

In the present specification, “deuterated” or “deuterated” means that hydrogen at a substitutable position of a compound is replaced with deuterium.

In the present specification, "perdeuterated" means a compound or group in which all hydrogens in the molecule are substituted or unsubstituted with deuterium, and has the same meaning as "100% deuterated".

In the present specification, "X% deuterated", "degree of deuteration X%", or "deuterium substitution rate X%" means that X% of hydrogen at substitutable positions in the structure is substituted with deuterium. For example, when the corresponding structure is dibenzofuran, "25% deuteration" of the dibenzofuran, "25% deuteration degree" of the dibenzofuran, or "25% deuterium substitution rate" of the dibenzofuran It means that two of the eight hydrogens at substitutable positions of dibenzofuran are substituted or unsubstituted with deuterium.

In the present specification, "degree of deuteration" or "deuterium substitution" refers to nuclear magnetic resonance spectroscopy (1H NMR), TLC/MS (Thin-Layer Chromatography/Mass Spectrometry), or GC/MS (Gas Chromatography/Mass Spectrometry). It can be confirmed by a known method.

Specifically, when analyzing "deuteration degree" or "deuterium substitution rate" by nuclear magnetic resonance spectroscopy (1H NMR), DMF (dimethylformamide) is added as an internal standard, and through the integration ratio on 1H NMR, The degree of deuteration or deuterium substitution rate can be calculated from the integrated amount of the total peak.

In this specification, D means deuterium.

In the present specification, in Formula 1, 0 to 100% of substitutable positions are substituted with deuterium.

In the present specification, in Formula 1, 0 to 90% of substitutable positions are substituted with deuterium.

In the present specification, in Formula 1, 0 to 80% of substitutable positions are substituted with deuterium.

In the present specification, in Formula 1, 5 to 80% of substitutable positions are substituted with deuterium.

In the present specification, in Formula 1, 8 to 80% of substitutable positions are substituted with deuterium.

In the present specification, in Formula 1, 10 to 80% of substitutable positions are substituted with deuterium.

An organic light emitting device including a compound of Formula 1 and/or Formula 2 having a deuterium substitution rate according to an exemplary embodiment of the present specification has improved heat resistance and improved lifespan.

According to an exemplary embodiment of the present specification, Formula 1 is any one of the following structural formulas.

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

In addition, by introducing various substituents into the core structure of the above structure, compounds having inherent characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light emitting layer materials, and electron transport layer materials used in the manufacture of organic light emitting devices into the core structure, materials satisfying the requirements of each organic layer can be synthesized. 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 layer of the organic material layers contains the aforementioned compound.

The organic light emitting device of the present invention may be manufactured by conventional organic light emitting device manufacturing methods and materials, except for forming one or more organic material layers using the above compounds.

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 means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer 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 hole injection and hole transport layer simultaneously, a light emitting layer, an electron transport layer, an electron injection layer, and the like as organic material layers. However, the structure of the organic light emitting diode is not limited thereto and may include a smaller number of organic material layers or a larger 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 Chemical Formula 1. Compounds may be included.

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 electron injection layer may include a compound represented by Chemical Formula 1.

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 Chemical Formula 1. Compounds may be included.

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 hole injection layer may include a compound represented by Chemical Formula 1.

In the organic light emitting device of the present invention, the first electrode is an anode, the second electrode is a cathode, the organic material layer includes a light emitting layer, and the organic material layer containing the compound is positioned between the light emitting layer and the anode.

In the organic light emitting device of the present invention, the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, hole transport layer, or electron blocking layer includes the compound.

In one 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/cathode

(2) anode/hole injection layer/hole transport layer/light emitting layer/cathode

(3) anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode

(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 / cathode

(9) anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(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 / cathode

(13) anode/hole injection layer/hole transport layer/electron suppression layer/emission layer/electron transport layer/electron injection layer/cathode

(14) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(15) anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode

(16) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(17) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(18) anode / hole injection layer / hole transport layer / electron suppression layer / light emitting layer / hole blocking layer / electron injection and transport layer / cathode

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

1 illustrates a structure of an organic light emitting device in which a first electrode 2, a light emitting organic material layer 3, and a second electrode 4 are sequentially stacked on a substrate 1. In this structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer 3 .

2, a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 8, a hole blocking layer 9 on a substrate 1, electron injection and A structure of an organic light emitting device in which the transport layer 10 and the second electrode 4 are sequentially stacked is illustrated. In this structure, the compound represented by Formula 1 may be included in the hole injection layer 5, the hole transport layer 6, or the electron blocking layer 7.

For example, the organic light emitting device according to the present invention uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or conductive metal oxide or an alloy thereof on a substrate. is deposited to form an anode, and from the group consisting of a hole injection layer, a hole transport layer, a hole transport and hole injection layer, a light emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons thereon. 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 fabricated 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, a light emitting layer and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer can be formed by a solvent process other than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method. Can be made in layers.

The anode is an electrode for injecting holes, and a material having a high work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode is an electrode for injecting electrons, and it is preferable that the cathode material is a material having a small work function so as 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 serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage, HOMO (highest occupied molecular orbital) is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto. The hole injection layer may have a thickness of 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristic from deteriorating, and if it 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 are advantages to avoiding this.

According to an exemplary embodiment of the present specification, the hole injection layer includes a compound represented by Chemical Formula HI-1, but is not limited thereto.

[Formula HI-1]

In the above formula HI-1,

At least one of X'1 to X'6 is N and the others are CH,

R309 to R314 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or bonded to adjacent groups to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, X'1 to X'6 are N.

According to an exemplary embodiment of the present specification, R309 to R314 are nitrile groups.

According to an exemplary embodiment of the present specification, Formula HI-1 is represented by the following compound.

The hole transport layer may play a role of facilitating hole transport. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by Formula HT-2, but is not limited thereto.

[Formula HT-2]

In the above formula HT-2,

R403 to R406 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; A substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof, or bonded to adjacent groups to form a substituted or unsubstituted ring,

L403 is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group;

l403 is an integer from 1 to 3, and when l403 is 2 or more, L403 is the same as or different from each other.

According to an exemplary embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; A substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represents a phenyl group, a biphenyl group, or a naphthyl group.

According to an exemplary embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represents a phenyl group.

According to an exemplary embodiment of the present specification, L403 is an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 3 to 30 carbon atoms substituted with an arylene group.

According to an exemplary embodiment of the present specification, L403 is a phenylene group, a divalent biphenyl group, or a divalent carbazole group unsubstituted or substituted with an aryl group.

According to one embodiment of the present specification, L403 is a divalent carbazole group substituted with a naphthyl group.

According to an exemplary embodiment of the present specification, Formula HT-2 is selected from the following compounds.

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

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. For the electron suppression layer, the aforementioned spiro compound or a material known in the art may be used.

The light emitting 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 the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.

A host material for the light emitting layer includes a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

According to an exemplary embodiment of the present specification, the host includes a compound represented by Formula H-1 below, but is not limited thereto.

[Formula H-1]

In the above formula H-1,

L20 and L21 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar20 and Ar21 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R201 is hydrogen; heavy hydrogen; halogen 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,

r201 is an integer of 1 to 8, and when r201 is 2 or more, two or more R201s are the same as or different from each other.

In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen; A biphenyl group unsubstituted or substituted with heavy hydrogen; A naphthylene group unsubstituted or substituted with heavy hydrogen; Divalent dibenzofuran group; or a divalent dibenzothiophene group.

In one embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to 4-cyclic heterocyclic group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently deuterium or a phenyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with heavy hydrogen or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; terphenyl group; A naphthyl group unsubstituted or substituted with heavy hydrogen; A thiophene group unsubstituted or substituted with a phenyl group; phenanthrene group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; or a naphthobenzothiophene group.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a 1-naphthyl group or a 2-naphthyl group.

According to an exemplary embodiment of the present specification, R201 is hydrogen.

According to an exemplary embodiment of the present specification, Formula H-1 is represented by the following compound.

When the light emitting layer emits red light, PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonateiridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) iridium) are used as light emitting dopants. ), 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 light emitting layer emits green light, a phosphorescent material 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 light emitting dopant. However, it is not limited thereto. When the light emitting layer emits blue light, as the light emitting dopant, a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distryarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited thereto.

According to an exemplary embodiment of the present specification, the dopant includes a compound represented by Formula D-1 below, but is not limited thereto.

[Formula D-1]

In the above formula D-1,

T1 to T6 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

t5 and t6 are each an integer from 1 to 4,

When t5 is 2 or more, the two or more T5s are the same as or different from each other,

When t6 is 2 or more, the 2 or more T6s are the same as or different from each other.

According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently hydrogen; a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a nitrile group or a linear or branched chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a straight chain or branched chain alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently hydrogen; A phenyl group substituted with a methyl group; or a dibenzofuran group.

According to an exemplary embodiment of the present specification, Formula D-1 is represented by the following compound.

A hole blocking 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 electron transport. As the electron transport material, a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include Al complexes 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 in preventing deterioration of electron transport properties, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in driving voltage to improve electron movement. There are advantages that can be

The electron injection layer may serve to smoothly inject electrons. The electron injecting material has the ability to transport electrons, has an excellent electron injecting effect from the cathode, a light emitting layer or a light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also , compounds having excellent thin film forming ability are preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preonylidene methane, anthrone, etc. and their derivatives, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

According to an exemplary embodiment of the present specification, the electron injection and transport layer includes a compound represented by Formula EI-1.

[Formula EI-1]

In the above formula EI-1,

At least one of Z11 to Z13 is N and the others are CH,

At least one of Z14 to Z16 is N and the others are CH,

L701 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar701 to Ar704 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

1701 is an integer of 1 to 4, and when 1701 is plural, L701 is the same as or different from each other.

According to an exemplary embodiment of the present specification, L701 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L701 is a phenylene group; a biphenylylene group; or a naphthylene group.

According to an exemplary embodiment of the present specification, L701 is a phenylene group; or a naphthylene group.

According to an exemplary embodiment of the present specification, Ar701 to Ar704 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms. .

According to an exemplary embodiment of the present specification, Ar701 to Ar704 are phenyl groups.

According to an exemplary embodiment of the present specification, Formula HB-1 is represented by the following compound.

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

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

According to an exemplary embodiment of the present specification, the hole blocking layer includes a compound represented by Formula HB-1.

[Formula HB-1]

In the above formula HB-1,

At least one of Z1 to Z3 is N and the others are CH,

L601 and L602 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar601 to Ar603 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L601 and L602 are the same as or different from each other, and each independently a phenylene group; a biphenylylene group; or a naphthylene group.

According to an exemplary embodiment of the present specification, Ar601 to Ar603 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms. .

According to an exemplary embodiment of the present specification, Ar601 to Ar603 are a phenyl group or a triphenylene group.

According to an exemplary embodiment of the present specification, Formula HB-1 is represented by the following compound.

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

The organic light emitting device of the present invention may be manufactured by conventional organic light emitting device manufacturing methods and materials, except for forming one or more organic material layers using the above compounds.

The preparation method of the compound of Chemical Formula 1 and the manufacture of an organic light emitting device using the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

In the reaction scheme below, various kinds of intermediates can be synthesized according to the appropriate selection of starting materials known to those skilled in the art for the type and number of substituents. Reaction type and reaction conditions may be used those known in the art.

All of the compounds represented by Chemical Formula 1 described herein can be prepared by appropriately combining the preparation formulas described in the examples herein and the intermediates based on common technical knowledge.

<Synthesis example>

Synthesis Example 1. Synthesis of Compound 1

2-chloro-7-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9,9′-spirobi[fluorene] (20.0 g, After adding toluene (200 ml) to diphenylamine (37.23 mmol), diphenylamine (6.43 g, 37.98 mmol), and sodium tert-butoxide (5.01 g, 52.12 mmol), the mixture was heated and stirred for 10 minutes. After adding bis(tri-tert-butylphosphine)palladium (0.10 g, 0.19 mmol) dissolved in toluene (10 ml) to the mixture, the mixture was heated and stirred for 1 hour. After completion of the reaction and filtration, layers were separated into toluene and water. After solvent removal, the compound 1 (20.0 g, 80.19% yield) was obtained by recrystallization with ethyl acetate. (MS[M+H]+ = 670)

Synthesis Example 2. Synthesis of Compound 2

2-chloro-7-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9,9′-spirobi[fluorene] (20.0 g, 37.23 mmol) and 4-(naphthalen-1-yl) -N -phenylaniline (11.22 g, 37.98 mmol), Compound 2 (23.5 g, 79.29% yield) was obtained in the same manner as in Synthesis Example 1. . (MS[M+H]+ = 796)

Synthesis Example 3. Synthesis of Compound 3

2-chloro-7-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9,9′-spirobi[fluorene] (20.0 g, Compound 3 (23.0 g , 78.59 % yield) was obtained. (MS[M+H]+ = 786)

Synthesis Example 4. Synthesis of Compound 4

2-chloro-7-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9,9′-spirobi[fluorene] (20.0 g, 37.23 mmol) and N -phenyldibenzo[ b , d ]furan-2-amine (9.85 g, 37.98 mmol) to obtain Compound 4 (22.0 g, 77.75% yield) in the same manner as in Synthesis Example 1. did (MS[M+H]+ = 760)

Synthesis Example 5. Synthesis of Compound 5

2-chloro-7-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9,9′-spirobi[fluorene] (20.0 g, 37.23 mmol) and N -(4-( tert -butyl)phenyl)-[1,1'-biphenyl]-4-amine (11.45 g, 37.98 mmol) to obtain the above compound in the same manner as in Synthesis Example 1. 5 (23.5 g, 78.69 % yield) was obtained. (MS[M+H]+ = 802)

Synthesis Example 6. Synthesis of Compound 6

2-chloro-7-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9,9′-spirobi[fluorene] (20.0 g, 37.23 mmol) and N- (4-( tert -butyl)phenyl)-9,9-dimethyl- 9H -fluoren-2-amine (12.97 g, 37.98 mmol) in the same manner as in Synthesis Example 1. The compound 6 (24.5 g, 78.14% yield) was obtained. (MS[M+H]+ = 842)

Synthesis Example 7. Synthesis of Compound 7

2-chloro-7-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9,9′-spirobi[fluorene] (20.0 g, 37.23 mmol) and N -([1,1'-biphenyl]-4-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine (13.50 g, 37.98 mmol) was used to obtain the compound 7 (25.0 g, 78.43% yield) in the same manner as in Synthesis Example 1. (MS[M+H]+ = 856)

Synthesis Example 8. Synthesis of Compound 8

2-chloro-7-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9,9′-spirobi[fluorene] (20.0 g, 37.23 mmol) and bis (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl) amine (14.80 g, 37.98 mmol) using the same synthesis example 1 Compound 8 (26.5 g, 79.95% yield) was obtained by the method. (MS[M+H]+ = 890)

Synthesis Example 9. Synthesis of Compound 9

2-chloro-7-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-1-yl)-9,9′-spirobi[fluorene] (20.0 g, 37.23 mmol) and diphenylamine (6.43 g, 37.98 mmol) to obtain Compound 9 (19.5 g, 78.19% yield) in the same manner as in Synthesis Example 1. (MS[M+H]+ = 670)

Synthesis Example 10. Synthesis of Compound 10

2-chloro-7-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-1-yl)-9,9′-spirobi[fluorene] (20.0 g, 37.23 mmol) and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-1-yl)amine (14.80 g, 37.98 mmol) using the same synthesis example 1 Compound 10 (26.0 g, 78.44% yield) was obtained by the method. (MS[M+H]+ = 890)

Synthesis Example 11. Synthesis of Compound 11

2-chloro-7-(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl)-9,9'spirobi[fluorene] (20.0 g, 32.61 mmol) and diphenylamine (5.63 g, 33.27 mmol) were used to obtain Compound 11 (19.0 g, 78.10% yield) in the same manner as in Synthesis Example 1. (MS[M+H]+ = 746)

Synthesis Example 12. Synthesis of Compound 12

2-chloro-7-(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl)-9,9'spirobi[fluorene] (20.0 g, 32.61 mmol) and 5,5,8,8-tetramethyl- N -phenyl-5,6,7,8-tetrahydronaphthalen-2-amine (9.30 g, 33.27 mmol). Compound 12 (21.5 g, 77.00% yield) was obtained in the same manner as in Example 1. (MS[M+H]+ = 856)

Synthesis Example 13. Synthesis of Compound 13

Compound 1 (20.0 g, 29.85 mmol) obtained in Synthesis Example 1 was put into benzene-d6 (200 ml) and completely dissolved, then trifluoromethanesulfonic acid (1.3 ml, 14.93 mmol) was added and stirred for 25 minutes. After completion of the reaction, dichloromethane was added, and the layers were separated to obtain an organic layer. After drying with anhydrous magnesium sulfate (MgSO4), it was filtered. The filtrate was concentrated under reduced pressure and recrystallized with ethyl acetate to obtain the compound 13 (16.0 g, 76.89%). (MS[M+H]+ = 697)

Synthesis Example 14. Synthesis of Compound 14

Compound 14 (16.0 g, 77.99% yield) was obtained in the same manner as in Synthesis Example 13 using Compound 8 (20.0 g, 22.46 mmol) obtained in Synthesis Example 8. (MS[M+H]+ = 913)

<Experimental Example and Comparative Experimental Example>

Experimental Example 1-1

A glass substrate coated with ITO (Indium Tin Oxide) to a thickness of 1,400 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum deposition machine.

A compound represented by Chemical Formula HAT was thermally vacuum deposited to a thickness of 100 Å on the prepared ITO transparent electrode to form a hole injection layer. After vacuum depositing a compound represented by Formula HT1 to a thickness of 1150 Å as a hole transport layer thereon, Compound 1 prepared in Synthesis Example 1 was thermally vacuum deposited to a thickness of 150 Å as an electron blocking layer. Subsequently, as a light emitting layer, a compound represented by Chemical Formula BH and a compound represented by Chemical Formula BD were vacuum deposited to a thickness of 200 Å at a weight ratio of 25:1. Subsequently, as a hole blocking layer, a compound represented by Formula HB1 was vacuum deposited to a thickness of 50 Å. Subsequently, a compound represented by the following formula ET1 and a compound represented by the following Liq were thermally vacuum deposited to a thickness of 310 Å at a weight ratio of 1:1 as a layer capable of simultaneously transporting and injecting electrons. An organic light emitting diode was manufactured by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1000 Å to form a cathode on the electron transport and electron injection layers.

Experimental Examples 1-2 to 1-12 and Comparative Experimental Examples 1-1 to 1-3

Experimental Examples 1-2 to 1-12 and Comparative Experimental Example 1-1 in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1 in Experimental Example 1-1. The organic light emitting device of 1-3 was manufactured.

When a current of 10 mA/cm ² was applied to the organic light emitting device prepared in Experimental Example and Comparative Experimental Example, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. Meanwhile, T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

electron suppression layer Voltage (V @ 10mA/cm ² ) Efficiency (cd/A @ 10mA/cm ² ) color coordinates (x, y) life span
(T95, hr) Experimental Example 1-1 compound 1 3.68 5.92 0.140, 0.043 175 Experimental Example 1-2 compound 2 3.67 5.90 0.141, 0.043 165 Experimental Example 1-3 compound 4 3.67 5.90 0.140, 0.044 165 Experimental Example 1-4 compound 5 3.65 5.88 0.141, 0.043 170 Experimental Example 1-5 compound 7 3.64 5.87 0.140, 0.043 170 Experimental Example 1-6 compound 8 3.65 5.86 0.141, 0.044 170 Experimental Example 1-7 compound 9 3.68 5.90 0.140, 0.043 165 Experimental Example 1-8 compound 10 3.64 5.89 0.140, 0.043 170 Experimental Example 1-9 compound 11 3.67 5.90 0.140, 0.043 170 Experimental Example 1-10 compound 12 3.68 5.91 0.141, 0.043 165 Experimental Example 1-11 compound 13 3.68 5.92 0.140, 0.043 195 Experimental Example 1-12 compound 14 3.65 5.86 0.141, 0.044 195 Comparative Experimental Example 1-1 EB1 4.52 3.51 0.145, 0.049 20 Comparative Experimental Example 1-2 EB2 4.31 4.64 0.145, 0.049 95 Comparative Experimental Example 1-3 EB3 4.13 4.39 0.145, 0.048 25

As shown in Table 1, it was confirmed that the compound of the present invention has excellent electron suppression ability, and thus the organic light emitting device using the compound as an electron suppression layer exhibits remarkable effects in terms of driving voltage, efficiency, and lifetime.

Comparative Experimental Example 1-1 formed a fluorene ring substituted with R4 and R5 of Formula 1 of the present invention and used compound EB1 not containing an amine group, and Comparative Experimental Example 1-3 used the core of Formula 1 of the present invention The compound EB3 not containing was used.

In the case of Experimental Examples 1-1 to 1-12 using the compound of Formula 1 of the present invention, it can be seen that they have lower voltage, higher efficiency, and significantly improved lifetime than Comparative Experimental Examples 1-1 and 1-3.

Comparative Experimental Example 1-2 uses the compound EB2 containing two amine groups unlike the present invention. It can be seen that Experimental Examples 1-1 to 1-12 using the compound of Formula 1 of the present invention have lower voltage, higher efficiency, and significantly improved lifetime than Comparative Experimental Example 1-2.

Experimental Examples 1-1 to 1-12 have superior effects in terms of voltage, efficiency, and lifetime than Comparative Experimental Example 1-2.

Experimental Examples 2-1 to 2-12 and Comparative Experimental Examples 1-1, 2-1 to 2-3

Except for using the compound represented by Formula EB1 instead of Compound 1 as the electron blocking layer in Experimental Example 1-1 and using the compound shown in Table 2 instead of the compound represented by Formula HT1 as the hole transport layer, Organic light emitting devices of Experimental Examples 2-1 to 2-12 and Comparative Experimental Examples 2-1 to 2-3 were manufactured in the same manner as in Experimental Example 1-1. When a current of 10 mA/cm ² was applied to the organic light emitting device prepared in Experimental Example and Comparative Experimental Example, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 2 below. Meanwhile, T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

hole transport layer Voltage (V @ 10mA/cm ² ) Efficiency (cd/A @ 10mA/cm ² ) color coordinates (x, y) life span
(T95, hr) Experimental example 2-1 compound 1 3.70 5.90 0.140, 0.043 170 Experimental Example 2-2 compound 3 3.65 5.92 0.141, 0.044 170 Experimental example 2-3 compound 5 3.66 5.92 0.140, 0.043 170 Experimental Example 2-4 compound 6 3.63 5.95 0.140, 0.043 175 Experimental example 2-5 compound 7 3.66 5.94 0.140, 0.043 165 Experimental example 2-6 compound 8 3.63 5.97 0.141, 0.044 175 Experimental Example 2-7 compound 9 3.69 5.92 0.140, 0.043 165 Experimental Example 2-8 compound 10 3.65 5.94 0.140, 0.043 170 Experimental Example 2-9 compound 11 3.69 5.94 0.140, 0.044 170 Experimental example 2-10 compound 12 3.66 5.95 0.141, 0.043 170 Experimental Example 2-11 compound 13 3.70 5.90 0.140, 0.043 185 Experimental Example 2-12 compound 14 3.63 5.97 0.141, 0.044 185 Comparative Experimental Example 1-1 HT1 4.52 3.51 0.145, 0.049 20 Comparative Experimental Example 2-1 HT2 4.38 3.68 0.145, 0.049 35 Comparative Experimental Example 2-2 HT3 3.95 5.02 0.145, 0.049 90 Comparative Experimental Example 2-3 HT4 4.28 4.25 0.144, 0.049 45

In Comparative Experimental Example 2-1, a compound HT2 in which R4 and R5 of Formula 1 of the present invention form a substituted fluorene ring and does not contain an amine group was used, and in Comparative Experimental Example 2-2, a compound containing two amine groups HT3 was used, and in Comparative Experimental Example 2-3, the compound HT4, which did not contain an amine group and did not contain the fluorene core structure of Formula 1 of the present invention, was used.

Experimental Examples 2-1 to 2-12 are lower than Comparative Experimental Examples 1-1 and 2-3 using compounds that do not contain the fluorene core of Formula 1 and contain two or no amine groups. voltage, high efficiency and significantly increased lifetime.

As shown in Table 2, it was confirmed that the compound of the present invention has excellent hole transport ability, and thus the organic light emitting device using the compound as a hole transport layer exhibits remarkable effects in terms of driving voltage, efficiency, and lifetime.

1: substrate
2: anode
3: organic material layer
4: cathode
5: hole injection layer
6: hole import layer
7: electron suppression layer
8: light emitting layer
9: hole blocking layer
10: electron injection and transport layer

Claims (17)

A compound of Formula 1:
[Formula 1]

In Formula 1,
R2 and R3 are the same as or different from each other, and are each independently hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted An arylalkyl group, a substituted or unsubstituted arylalkenyl group, or a substituted or unsubstituted heteroaryl group,
R4 and R5 combine with each other to form a substituted or unsubstituted hydrocarbon ring,
Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl group. A heteroaryl group or a hydrocarbon ring group in which a substituted or unsubstituted aliphatic ring and an aromatic ring are condensed,
L, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted divalent alkoxy group, a substituted or unsubstituted divalent arylalkenyl group, a substituted or unsubstituted divalent arylalkenyl group, A cyclic arylene group, or a substituted or unsubstituted heteroarylene group,
R1 is Formula 2;
[Formula 2]

In Formula 2, the dotted line is a site that binds to L,
R6 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group;
m is an integer from 0 to 3, and when m is 2 or more, R2 is the same as or different from each other;
n is an integer from 0 to 3, and when n is 2 or more, R3 is the same as or different from each other;
l is an integer from 0 to 11, and when l is 2 or more, R6 is the same as or different from each other. The compound according to claim 1, wherein Formula 1 is Formula 1-1 or Formula 1-2:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,
The definitions of R2 to R6, L, L1, L2, Ar1, Ar2, n, m, and l are as defined in Formulas 1 and 2 above. The method according to claim 1, wherein L, L1 and L2 are the same as or different from each other, and each independently represents a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. A compound which is a rene group. The compound according to claim 1, wherein R4 and R5 combine with each other to form a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms. The compound of claim 1, wherein Formula 1 is Formula 1-3 or 1-4 below:
[Formula 1-3]

[Formula 1-4]

In Formulas 1-3 and 1-4, R2, R3, R6, L, L1, L2, Ar1, Ar2, l, m and n are as defined in Formulas 1 and 2 above. The compound according to claim 1, wherein R6 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. The method according to claim 1, wherein R2 and R3 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. , Or a compound that is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. The method according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted carbon number. A compound that is a hydrocarbon ring group in which a 3 to 30 heteroaryl group, or a substituted or unsubstituted C 3 to 30 aliphatic ring and an aromatic ring are condensed. The compound of claim 1, wherein 0 to 100% of substitutable positions in Formula 1 are substituted with deuterium. The compound according to claim 1, wherein one of Ar1 and Ar2 is a hydrocarbon ring group in which a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring are condensed. The compound according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and are each independently a hydrocarbon ring group in which a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring are condensed. The compound according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms. The compound according to claim 1, wherein Ar1 is an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, and Ar2 is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. The compound of claim 1, wherein Formula 1 is any one of the following structural formulas:












a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound according to any one of claims 1 to 14. . The organic light emitting device of claim 15, wherein the first electrode is an anode, the second electrode is a cathode, the organic material layer includes a light emitting layer, and the organic material layer including the compound is positioned between the light emitting layer and the anode. . The organic light emitting device of claim 15, wherein the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer includes the compound.