CN113196515A

CN113196515A - Organic light emitting device

Info

Publication number: CN113196515A
Application number: CN202080006746.7A
Authority: CN
Inventors: 金明坤; 许瀞午; 洪玩杓; 金京嬉; 金恩镐
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2019-07-31
Filing date: 2020-07-31
Publication date: 2021-07-30
Anticipated expiration: 2040-07-31
Also published as: KR102406148B1; CN113196515B; KR20210015723A; WO2021020947A1

Abstract

The present specification relates to an organic light emitting device, comprising: a first electrode; a second electrode provided to face the first electrode, and an organic material layer provided between the first electrode and the second electrode, the organic material layer including: a layer comprising the compound of chemical formula 1, and a layer comprising the compound of chemical formula 2.

Description

Organic light emitting device

Technical Field

The present description relates to organic light emitting devices.

This application claims priority to korean patent application No. 10-2019-0093179, filed by the korean patent office at 31.07.2019, the entire contents of which are incorporated herein by reference.

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between two electrodes, holes are injected from an anode into an organic layer, electrons are injected from a cathode into the organic layer, an exciton (exiton) is formed when the injected holes and electrons meet, and light is emitted when the exciton falls back to a ground state.

There is a continuing demand for the development of new materials for organic light emitting devices as described above.

Disclosure of Invention

Technical subject

The present specification provides an organic light emitting device.

Means for solving the problems

The present specification provides an organic light emitting device, comprising: a first electrode; a second electrode; and an organic material layer provided between the first electrode and the second electrode,

the organic layer includes: a first organic layer including a compound represented by the following chemical formula 1 and a second organic layer including a compound represented by the following chemical formula 2.

[ chemical formula 1]

In the above-described chemical formula 1,

a1, A2, A3, B1 and B2, which may be the same or different from each other, are each independently a hydrocarbon ring,

r1 to R5, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group, or are represented by the following chemical formula 3, at least one or more of R1 to R5 are represented by the following chemical formula 3,

[ chemical formula 3]

In the above-mentioned chemical formula 3,

the dotted line is a site linked to A1, A2, A3, B1 or B2,

x is C or Si, and X is C or Si,

r6 to R8, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group,

n1 and n5 are each an integer of 0 to 4,

n2 and n4 are each an integer of 0 to 5,

n3 is an integer from 0 to 3,

n1+ n2+ n3+ n4+ n5 is 1 or more,

when n1 to n5 are 2 or more, the substituents in parentheses may be the same or different from each other,

[ chemical formula 2]

In the above-described chemical formula 2,

y31 and Y32, which are the same or different from each other, are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or combine with each other to form a substituted or unsubstituted ring,

r3-1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the following chemical formula 4, or combines with each other to form a hydrocarbon ring,

a31 is an integer from 0 to 8,

a31 is plural, R3-1 may be the same or different from each other,

[ chemical formula 4]

In the above-mentioned chemical formula 4,

the dotted line is a site connected to the nucleus,

Ar₄₁and Ar₄₂The same or different from each other, each independently is a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

X₁to X₃Identical to or different from each other, each independently is N or CR ",

X₁to X₃At least one of which is N,

r' is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group,

L₁to L₃Are the same or different from each other and are each independentlyA direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.

Effects of the invention

The organic light emitting device described in the present specification has a low driving voltage, excellent efficiency characteristics, and an excellent lifetime by including the compound represented by chemical formula 1 in the first organic layer and the compound represented by chemical formula 2 in the second organic layer. Specifically, the electron transport degree is adjusted by adjusting the appropriate HOMO level and LUMO level, so that low driving voltage, high efficiency, and lifetime can be improved.

Drawings

Fig. 1,2, and 8 to 10 illustrate examples of an organic light emitting device according to an embodiment of the present specification.

Fig. 3 to 7 illustrate examples of organic light emitting devices including 2 or more sets of stacks.

[ description of symbols ]

1: substrate/2: anode/3: hole injection layer/4: hole transport layer/4 a: first hole transport layer/4 b: second hole transport layer/4 c: third hole transport layer/4 d: fourth hole transport layer/4 e: fifth hole transport layer/4 f: sixth hole transport layer/4 p: p-doped hole transport layer/4R: red hole transport layer/4G: green hole transport layer/4B: blue hole transport layer/5: electron blocking layer/6: light-emitting layer/6 a: first light-emitting layer/6 b: second light-emitting layer/6 c: third light-emitting layer/6 BF: blue fluorescent light-emitting layer/6 BFa: first blue fluorescent light-emitting layer/6 BFb: second blue fluorescent light-emitting layer/6 YGP: yellow-green phosphorescent light-emitting layer/6 RP: red phosphorescent emission layer/6 GP: green phosphorescent light-emitting layer/7: hole blocking layer/8: electron injection and transport layer/9: electron transport layer/9 a: first electron transport layer/9 b: second electron transport layer/9 c: third electron transport layer/10: electron injection layer/11: cathode/12: n-type charge generation layer/12 a: first N-type charge generation layer/12 b: second N-type charge generation layer/13: p-type charge generation layer/13 a: first P-type charge generation layer/13 b: second P-type charge generation layer/14: covering layer

Detailed Description

The present specification will be described in more detail below.

The present specification provides an organic light emitting device including both a first organic layer including a compound represented by chemical formula 1 and a second organic layer including a compound represented by chemical formula 2. The light emitting layer including the compound of the above chemical formula 1 has a shallow HOMO level, and the compound of the above chemical formula 2 has a deep HOMO, LUMO level, and thus electrons can be easily transferred to the light emitting layer, thereby exhibiting high efficiency and lifetime.

In the present specification, examples of the substituent are described below, but the substituent is not limited thereto.

In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.

In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the other member but also a case where the other member exists between the two members.

In this specification, the dotted line or

Indicates a site to which another substituent or a binding moiety binds.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.

In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group (-CN), a nitro group, a hydroxyl group, a silyl group, a boryl group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a cycloalkyl group, an aryl group, an amino group, and a heterocyclic group, or a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent.

In the present specification, the connection of 2 or more substituents means that the hydrogen of any one substituent is replaced with another substituent. For example, isopropyl and phenyl are linked to form

Such a substituent.

In the present specification, the connection of 3 substituents includes not only the connection of (substituent 1) - (substituent 2) - (substituent 3) continuously but also the connection of (substituent 2) and (substituent 3) to (substituent 1). For example, 2 phenyl groups and isopropyl groups are linked to form

Such a substituent. The same applies to the case where 4 or more substituents are linked.

In the present specification, "substituted with a or B" includes not only the case of being substituted with only a or the case of being substituted with only B, but also the case of being substituted with a and B.

In the present specification, "substituted or unsubstituted" means that the substituent is substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group (-CN), a nitro group, a hydroxyl group, a silyl group, a boryl group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an arylthio group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an amino group, and a heterocyclic group having 2 to 30 carbon atoms, or is substituted with a substituent in which 2 or more groups selected from the above group are linked, or does not have any substituent.

In the present specification, "substituted or unsubstituted" means that the substituent is substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group (-CN), nitro, hydroxyl, silyl, boryl, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an amino group, and a heterocyclic group having 2 to 20 carbon atoms, or is substituted with a substituent in which 2 or more groups selected from the above group are linked, or does not have any substituent

Examples of the above-mentioned substituent are described below, but the substituent is not limited thereto.

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

In the present specification, the alkyl group includes a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is 1 to 60, 1 to 30, or 1 to 20. Specific examples of the above alkyl group include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl and the like, and the above alkyl group may be straight or branched, and according to one example, propyl includes n-propyl and isopropyl, and butyl includes n-butyl, isobutyl and tert-butyl.

In the present specification, the number of carbon atoms of the cycloalkyl group is not particularly limited, but is 3 to 60, 3 to 30, 3 to 20, or 3 to 10. Cycloalkyl groups include not only monocyclic groups but also bicyclic groups such as bridgehead (bridged head), fused ring (fused ring), spiro (spiro) and the like. Specifically, there are, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, and the like.

In the present specification, the cycloolefin (cycloalkene) is a cyclic group in which a double bond exists in a hydrocarbon ring but is not aromatic, and the number of carbon atoms is not particularly limited but is 3 to 60, 3 to 30, 3 to 20, or 3 to 10. The cycloolefin includes not only monocyclic groups but also bicyclic groups such as bridgehead, condensed ring, spiro ring and the like. Examples of the cycloolefin include, but are not limited to, cyclopropene, cyclobutene, cyclopentene, and cyclohexene.

In the present specification, an alkoxy group is a group having an aryl group bonded to an oxygen atom, an alkylthio group is a group having an alkyl group bonded to a sulfur atom, and the above description of the alkyl group can be applied to the alkyl group of the alkoxy group and the alkylthio group.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and the number of carbon atoms is not particularly limited but is 6 to 60, 6 to 30, or 6 to 20. The monocyclic aryl group may be, but is not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, and the like. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylene group, a triphenyl group, a perylene group,

Examples of the group include, but are not limited to, a fluorenyl group, a fluoranthenyl group, and a triphenylenyl group.

In the present specification, the carbon atom (C) No. 9 of the fluorenyl group may be substituted with an alkyl group, an aryl group or the like, and 2 substituents may be bonded to each other to form a spiro structure such as cyclopentane, fluorene or the like.

In the present specification, the substituted aryl group may include a form in which an aliphatic ring is fused to the aryl group. For example, the tetrahydronaphthyl groups of the structures described below are included in substituted aryl groups. In the following structures, one of the carbons of the benzene ring may be attached at another position.

In this specification, aryloxy is a group having an aryl group bonded to an oxygen atom, arylthio is a group having an aryl group bonded to a sulfur atom, and the above description about aryl groups can be applied to aryl groups of aryloxy and arylthio. The aryl group of the aryloxy group is exemplified by the above aryl groups. Specifically, the aryloxy group includes phenoxy, p-tolyloxy, m-tolyloxy, 3, 5-dimethylphenoxy, 2,4, 6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-Anthracenyloxy, 2-anthracenyloxy, 9-anthracenyloxy, 1-phenanthrenyloxy, 3-phenanthrenyloxy, 9-phenanthrenyloxy and the like as arylthio group (S) ((S))

Aryl thio), there are phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio and the like, but not limited thereto.

In the present specification, the silyl group may be represented by-SiY_aY_bY_cThe above-mentioned chemical formula is Y_a、Y_bAnd Y_cMay each be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a dimethylphenylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

In this specification, the boron group may be represented BY-BY_dY_eThe above-mentioned chemical formula is Y_dAnd Y_eMay each be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl. Specific examples of the silyl group include, but are not limited to, a dimethylboronyl group, a diethylboronyl group, a tert-butylmethylboronyl group, a vinylmethylboronyl group, a propylmethylboronyl group, a methylphenylboronyl group, a diphenylboronyl group, and a phenylboronyl group.

In the present specification, the amine group may be represented by — NRaRb, and the above Ra and Rb may each be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, but are not limited thereto. The amine group may be selected from an alkylamino group, an alkylarylamino group, an arylamino group, a heteroarylamino group, an alkylheteroarylamino group, and an arylheteroarylamino group, depending on the kind of the substituent (Ra, Rb) bonded thereto.

In the present specification, an alkylamino group means an amino group substituted with an alkyl group, and the number of carbon atoms is not particularly limited, but may be 1 to 40, 1 to 20. Specific examples of the alkylamino group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, and a diethylamino group.

In the present specification, as examples of the arylamine group, there are a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted arylheteroarylamine group. The aryl group in the above arylamine group may be a monocyclic or polycyclic aryl group. Specific examples of the arylamine group include a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a diphenylamino group, a phenylnaphthylamino group, a bis (tert-butylphenyl) amino group and the like, but the arylamine group is not limited thereto.

In the present specification, as examples of the heteroarylamino group, there are a substituted or unsubstituted monoheteroarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted arylheteroarylamino group.

In the present specification, arylheteroarylamino means an amino group substituted with an aryl group and a heteroaryl group, and the description about the above aryl group and the later-described heteroaryl group can be applied.

In the present specification, the heterocyclic group is a cyclic group containing N, O, S and 1 or more of Si as heteroatoms, and the number of carbon atoms is not particularly limited, but is 2 to 60, or 2 to 30. Examples of the heterocyclic group include pyridyl, quinolyl, thienyl, dibenzothienyl, furyl, dibenzofuryl, naphthobenzofuryl, carbazolyl, benzocarbazolyl, naphthobenzothienyl, hexahydrocarbazolyl, dihydroacridinyl and dibenzoazasilyl; phen

Oxazines (phenoxazines), phenothiazines (phenothiazines), dihydrodibenzoazasilyl groups; spiro (dibenzothiaole-dibenzoazasilyl) group; spiro (acridine-fluorene) group; spiro (fluorene-xanthene) group; spiro (fluorene-thioxanthene), etc., but is not limited thereto.

In the present specification, the heteroaryl group is an aromatic group, and the above description of the heterocyclic group can be applied thereto.

In the present specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent closest in steric structure to the substituent, or another substituent substituted on an atom substituted with the substituent.

In the present specification, "a ring formed by bonding adjacent groups" means a hydrocarbon ring or a heterocyclic ring.

In the present specification, the "five-or six-membered ring formed by bonding adjacent groups" means that the ring containing the substituent participating in the ring formation is a five-or six-membered ring. It is possible to include a case where an additional ring is fused to the above-mentioned ring containing the substituent participating in the ring formation.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or a fused ring of an aromatic and aliphatic, the aromatic hydrocarbon ring may be the aromatic ring except for having a valence of 1, and the aromatic ring may be the aromatic ring, and the aliphatic hydrocarbon ring may be the cycloalkyl ring except for having a valence of 1. Examples of the aromatic and aliphatic condensed ring include, but are not limited to, 1,2,3, 4-tetrahydronaphthyl and 2, 3-dihydro-1H-indenyl.

In the present specification, the description of the heterocyclic group is applicable except that the heterocyclic group is not 1-valent.

In the present specification, the aromatic hydrocarbon ring means a planar ring in which pi electrons are completely conjugated, and the above description on the aryl group can be applied in addition to the 2-valent group.

In the present specification, the aliphatic hydrocarbon ring means all hydrocarbon rings except for the aromatic hydrocarbon ring, and may include a cycloalkyl ring. The cycloalkyl ring can be used in addition to the 2-valent group, as described above with respect to the cycloalkyl group. In the substituted aliphatic hydrocarbon ring, an aliphatic hydrocarbon ring fused with an aromatic ring is also included.

In the present specification, the above description about aryl groups can be applied to arylene groups other than those having a valence of 2.

In the present specification, the above description on the cycloalkyl group can be applied to cycloalkylene groups other than the 2-valent group.

Next, chemical formula 1 will be described.

[ chemical formula 1]

In one embodiment of the present specification, a1 to A3, B1 and B2 are the same or different from each other, and each is independently a monocyclic or bicyclic hydrocarbon ring.

In one embodiment of the present specification, a1 to A3, B1 and B2 are the same as or different from each other, and each is independently a benzene ring or a naphthalene ring.

In one embodiment of the present specification, each of a1 to A3 is a benzene ring.

In one embodiment of the present specification, B1 and B2 are each a benzene ring.

In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 1-1.

[ chemical formula 1-1]

In the above chemical formula 1-1, R1 to R5 and n1 to n5 are the same as defined in the above chemical formula 1.

In one embodiment of the present specification, R1 to R5, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group, or are represented by the above chemical formula 3.

In one embodiment of the present specification, R1, R2, R4 and R5, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or are represented by the above chemical formula 3.

In one embodiment of the present specification, R1, R2, R4, and R5 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylamine group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or represented by the above chemical formula 3.

In one embodiment of the present specification, R1, R2, R4, and R5 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 18 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 12 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroarylamine group having 2 to 40 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or represented by the above chemical formula 3.

In one embodiment of the present specification, R1, R2, R4 and R5, equal to or different from each other, are each independently hydrogen; deuterium; a halogen group; a cyano group; an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 30 carbon atoms which is substituted or unsubstituted with deuterium; an arylamine group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group and an alkyl group having 1 to 10 carbon atoms or a substituent formed by connecting 2 or more groups selected from the above group; a heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with deuterium, or represented by the above chemical formula 3.

In one embodiment of the present specification, R1, R2, R4 and R5, equal to or different from each other, are each independently hydrogen; deuterium; a halogen group; a cyano group; an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 20 carbon atoms which is substituted or unsubstituted with deuterium; an arylamine group having 6 to 40 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group and an alkyl group having 1 to 6 carbon atoms or a substituent formed by connecting 2 or more groups selected from the above group; a heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with deuterium, or represented by the above chemical formula 3.

In one embodiment of the present specification, R1, R2, R4 and R5, equal to or different from each other, are each independently hydrogen; deuterium; a halogen group; cyano' an alkyl group having 1 to 6 carbon atoms substituted with deuterium; a cycloalkyl group having 3 to 20 carbon atoms; arylamine group having 6 to 40 carbon atoms; an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, a halogen group, a nitrile group, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms which is substituted with deuterium; a heterocyclic group having 2 to 20 carbon atoms, or represented by the above chemical formula 3.

In one embodiment of the present specification, the heterocyclic group of R1, R2, R4 and R5 contains N as a heteroatom.

In one embodiment of the present specification, R1, R2, R4 and R5, equal to or different from each other, are each independently hydrogen; deuterium; a fluorine group; a cyano group; methyl substituted or unsubstituted with deuterium; isopropyl group; a tertiary butyl group; a cyclohexyl group; a diphenylamino group; by deuterium, fluoro, cyano, tert-butyl or CD₃Substituted or unsubstituted phenyl; biphenyl radical(ii) a Naphthyl or pyridyl.

In one embodiment of the present specification, R3 is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group, or is represented by the following chemical formula 3.

In one embodiment of the present specification, R3 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or represented by the above chemical formula 3.

In one embodiment of the present specification, R3 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or represented by the above chemical formula 3.

In one embodiment of the present specification, R3 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 18 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 12 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 40 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or represented by the above chemical formula 3.

In one embodiment of the present description, R3 is hydrogen; deuterium; a halogen group; a cyano group; an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 30 carbon atoms which is substituted or unsubstituted with deuterium; an arylamine group having 6 to 60 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a silyl group, or a substituent in which 2 or more groups selected from the above group are bonded; an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium, a halogen group or a cyano group; a heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with deuterium, or represented by the above chemical formula 3.

In one embodiment of the present description, R3 is hydrogen; deuterium; a halogen group; a cyano group; an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 20 carbon atoms which is substituted or unsubstituted with deuterium; an arylamine group having 6 to 40 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group, or a substituent in which 2 or more groups selected from the above group are bonded; an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, a halogen group or a cyano group; a heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with deuterium, or represented by the above chemical formula 3.

In one embodiment of the present description, R3 is hydrogen; deuterium; a halogen group; a cyano group; an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 20 carbon atoms; an arylamine group having 6 to 40 carbon atoms which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, or a triarylamine group having 18 to 60 carbon atoms; an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, a halogen group or a cyano group; a heterocyclic group having 2 to 20 carbon atoms, or represented by the above chemical formula 3.

In one embodiment of the present specification, the heterocyclic group of R3 contains N as a heteroatom.

In one embodiment of the present description, R3 is hydrogen; deuterium; methyl substituted or unsubstituted with deuterium; a tertiary butyl group; diphenylamino substituted or unsubstituted with deuterium, tert-butyl, trimethylsilyl or triphenylsilyl; phenyl substituted or unsubstituted with deuterium or fluoro; or a carbazolyl group.

In one embodiment of the present specification, R1, R2, R4 and R5, equal to or different from each other, are each independently hydrogen; deuterium; a halogen group; a cyano group; an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 30 carbon atoms which is substituted or unsubstituted with deuterium; an arylamine group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group and an alkyl group having 1 to 10 carbon atoms or a substituent formed by connecting 2 or more groups selected from the above group; a heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with deuterium, or represented by the above chemical formula 3,

r3 is hydrogen; deuterium; a halogen group; a cyano group; an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 30 carbon atoms which is substituted or unsubstituted with deuterium; an arylamine group having 6 to 60 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a silyl group, or a substituent in which 2 or more groups selected from the above group are bonded; an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium, a halogen group or a cyano group; a heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with deuterium, or represented by the above chemical formula 3.

In one embodiment of the present description, one of R2 is attached at an ortho (ortho) oriented position relative to the N to which B2 is attached.

In one embodiment of the present description, one of R4 is attached in an ortho-oriented position relative to the N to which B2 is attached.

In one embodiment of the present specification, n1 is 1 or 2.

In one embodiment of the present specification, n2 is 1 to 4. In another embodiment, n2 is 1 to 3.

In one embodiment of the present specification, n3 is 1 or 2.

In one embodiment of the present specification, n4 is 1 to 4. In another embodiment, n4 is 1 to 3.

In one embodiment of the present specification, n5 is 1.

In one embodiment of the present specification, at least one or more of R1 to R5 is represented by the above chemical formula 3.

In one embodiment of the present specification, one to four of R1 to R5 are represented by the above chemical formula 3.

In one embodiment of the present specification, one or two of R1 to R5 are represented by the above chemical formula 3.

In one embodiment of the present specification, one to four of R1, R2, R4 and R5 are represented by the above chemical formula 3.

In one embodiment of the present specification, one or two of R1, R2, R4 and R5 are represented by the above chemical formula 3.

In one embodiment of the present specification, R1 is represented by chemical formula 3.

In one embodiment of the present specification, R2 is represented by chemical formula 3.

In one embodiment of the present specification, R3 is represented by chemical formula 3.

In one embodiment of the present specification, R4 is represented by chemical formula 3.

In one embodiment of the present specification, R5 is represented by chemical formula 3.

In one embodiment of the present specification, R6 to R8 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 or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R6 to R8, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R6 to R8, which are the same or different from each other, are each independently an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a silyl group, or a substituent in which 2 or more groups selected from the above group are bonded.

In one embodiment of the present specification, R6 to R8, which are the same or different from each other, are each independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group, or a substituent in which 2 or more groups selected from the above group are bonded.

In one embodiment of the present specification, R6 to R8, which are the same or different from each other, are each independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms which is substituted with deuterium, or a trialkylsilyl group having 3 to 18 carbon atoms.

In one embodiment of the present specification, R6 to R8, which are the same or different from each other, are each independently methyl; a tertiary butyl group; or by deuterium, fluoro, methyl, tert-butyl, CD₃Or phenyl substituted or unsubstituted with trimethylsilyl.

In one embodiment of the present specification, X is C and at least one of R6 to R8 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, X is C and at least two of R6 to R8 are substituted or unsubstituted alkyl groups.

In one embodiment of the present specification, X is C and at least one of R6 to R8 is a substituted or unsubstituted aryl.

In one embodiment of the present specification, X is C, R6 and R7, which may be the same or different from each other, are each independently a substituted or unsubstituted alkyl group, and R8 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, X is Si and at least one of R6 through R8 is a substituted or unsubstituted aryl.

In one embodiment of the present specification, X is Si and at least two of R6 through R8 are substituted or unsubstituted aryl groups.

In one embodiment of the present specification, X is C, R6 and R7, which may be the same or different from each other, are each independently a substituted or unsubstituted aryl group, and R8 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, X is Si, and R6 to R8, which may be the same or different from each other, are each independently a substituted or unsubstituted aryl group.

In one embodiment of the present specification, the chemical formula 3 is represented by the following chemical formula 3-1 or 3-2.

[ chemical formula 3-1]

[ chemical formula 3-2]

In the above chemical formulas 3-1 and 3-2,

x is the group consisting of Si,

r11 is a substituted or unsubstituted alkyl group,

r12 is a substituted or unsubstituted aryl group,

r13 to R16, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

In one embodiment of the present disclosure, the above descriptions about R6 to R8 can be applied to R11 to R16.

In one embodiment of the present specification, R11 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R11 is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, R11 is an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium.

In one embodiment of the present specification, R11 is methyl.

In one embodiment of the present specification, R12 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R12 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R12 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group, or with 2 or more groups selected from the above group.

In one embodiment of the present specification, R12 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms which is substituted with deuterium, or a trialkylsilyl group having 3 to 18 carbon atoms.

In one embodiment of the present specification, R12 is deuterium, fluoro, methyl, t-butyl, CD₃Or phenyl substituted or unsubstituted with trimethylsilyl.

In one embodiment of the present specification, R13 to R16 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 or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R13 to R16, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R13 to R16, which are the same or different from each other, are each independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group, or a substituent in which 2 or more groups selected from the above group are bonded.

In one embodiment of the present specification, R13 to R16, which are the same or different from each other, are each independently methyl; a tertiary butyl group; or by deuterium, fluoro, methyl, tert-butyl, CD₃Or phenyl substituted or unsubstituted with trimethylsilyl.

In one embodiment of the present specification, the compound represented by the above chemical formula 1 is any one selected from the following compounds.

Next, chemical formula 2 will be described.

In one embodiment of the present specification, Y31 and Y32 may be the same or different and each independently represent hydrogen, 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 may be bonded to each other to form a ring.

In one embodiment of the present specification, Y31 and Y32 may be the same or different and each independently represent hydrogen, 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 may be bonded to each other to form an aliphatic ring.

In one embodiment of the present specification, Y31 and Y32 may be the same or different and each independently represent hydrogen, 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 may be bonded to each other to form an aliphatic ring having 3 to 10 carbon atoms.

In one embodiment of the present specification, Y31 and Y32 are bonded to each other to form an alicyclic ring having 3 to 6 carbon atoms.

In one embodiment of the present disclosure, Y31 and Y32 are bonded to each other to form a cyclopentyl ring.

In one embodiment of the present specification, Y31 and Y32 are bonded to each other to form a ring in which an aliphatic ring having 3 to 10 carbon atoms and an aromatic ring are fused.

In one embodiment of the present specification, the above-mentioned Y31 and Y32 are bonded to each other to form a ring in which a cyclopentyl ring and a benzene ring are condensed.

In one embodiment of the present specification, Y31 and Y32 are the same as or different from each other, and each independently represents hydrogen, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Y31 and Y32, which are the same or different from each other, are each independently hydrogen, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, terphenyl, phenanthryl, or anthryl,

the above-mentioned phenyl, biphenyl, naphthyl, terphenyl, phenanthryl or anthryl group is substituted or unsubstituted by a methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, terphenyl, phenanthryl or anthryl group.

In one embodiment of the present specification, Y31 and Y32 may be the same or different and each independently hydrogen, methyl, phenyl, naphthyl, phenyl substituted with methyl, naphthyl substituted with methyl, phenyl substituted with naphthyl, naphthyl substituted with phenyl, or an aliphatic ring having 3 to 6 carbon atoms formed by bonding to each other.

In one embodiment of the present specification, R3-1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the above chemical formula 4, or is combined with adjacent groups to form a hydrocarbon ring.

In one embodiment of the present specification, R3-1 is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or the above chemical formula 4, or is bonded to an adjacent group to form a hydrocarbon ring having 3 to 20 carbon atoms.

In one embodiment of the present specification, R3-1 is hydrogen, methyl, tert-butyl, phenyl substituted with methyl, biphenyl, naphthyl, or the above chemical formula 4, or is bonded to an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.

In one embodiment of the present specification, R3-1 is hydrogen, methyl, tert-butyl, phenyl, naphthyl, or the above chemical formula 4, or is bonded to an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.

In one embodiment of the present specification, R3-1 is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present disclosure, a31 is an integer of 1 to 8, and one or more R3-1 is the chemical formula 4.

In one embodiment of the present specification, Ar is₄₁And Ar₄₂The alkyl group having 1 to 10 carbon atoms which may be substituted or unsubstituted, the alkylsilyl group which may be substituted or unsubstituted, the aryl group having 6 to 30 carbon atoms which may be substituted or unsubstituted, or the heterocyclic group having 3 to 30 carbon atoms which may be substituted or unsubstituted, respectively.

In this specificationIn one embodiment of the book, Ar is₄₁And Ar₄₂The alkyl group having 1 to 10 carbon atoms, the silyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms, the aryl group having 6 to 30 carbon atoms, or the heterocyclic group having 3 to 30 carbon atoms, which are the same or different from each other, may be substituted or unsubstituted.

In one embodiment of the present specification, Ar is₄₁And Ar₄₂The same or different from each other, each independently is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms.

In one embodiment of the present specification, Ar is₄₁And Ar₄₂The same or different from each other, each independently is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar is₄₁And Ar₄₂Identical to or different from each other, each independently is methyl, ethyl, butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, perylene, fluorenyl, fluorenylxanthenyl, carbazolyl, benzocarbazolyl, indenocarbazolyl, pyridyl, pyrimidyl, triazinyl, dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl, thiophene

Oxazinyl, phenothiazinyl, pheno

A thienyl (phenoxathiine), a trimethylsilyl group,

the above-mentioned phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, triphenylene group, perylene group, fluorenyl group, fluorenylxanthenyl group, carbazolyl group, benzocarbazolyl group, indenocarbazolyl group, pyridyl group, pyrimidyl group, triazinyl group, dibenzofuranyl group, dibenzothienyl group, quinolyl group, quinazolinyl group, quinoxalyl group, thiophene group

Oxazinyl, phenothiazinyl, pheno

The thiayl group is substituted or unsubstituted with any one or more selected from deuterium, CN, methyl, tert-butyl, phenyl substituted with a methyl group, trifluoromethyl, trifluoromethoxy, pyridyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, trimethylsilyl, triphenylsilyl, and carbazolyl.

In one embodiment of the present specification, Ar is₄₁And Ar₄₂Identical or different from one another, are each independently phenyl, biphenyl, terphenyl, naphthyl or phenanthryl, which are unsubstituted or substituted by deuterium, CN, alkyl, aryl, silyl or heteroaryl.

In one embodiment of the present specification, Ar is₄₁And Ar₄₂The same or different from each other, each independently is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group or a phenanthryl group, the above phenyl group, biphenyl group, terphenyl group, naphthyl group or phenanthryl group being substituted or unsubstituted with deuterium, CN, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present specification, Ar is₄₁And Ar₄₂The same or different from each other, each independently is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group or a phenanthryl group, the above phenyl group, biphenyl group, terphenyl group, naphthyl group or phenanthryl group being substituted or unsubstituted by any one or more selected from deuterium, CN, methyl, ethyl, butyl, tert-butyl, phenyl, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, anthryl group, perylenyl group, triphenylene group, pyrenyl group, anthryl group, thienyl group, furyl group, pyridyl group, pyrimidinyl group, triazinyl group, carbazolyl group, dibenzofuranyl group or dibenzothienyl group.

In one embodiment of the present specification, X is₁To X₃Is N.

In this specificationIn one embodiment of the book, X is₁To X₃X in (1)₁Is N, the rest is CR.

In one embodiment of the present specification, X is₁To X₃X in (1)₂Is N, the rest is CR.

In one embodiment of the present specification, X is₁To X₃X in (1)₃Is N, the rest is CR.

In one embodiment of the present specification, X is₁To X₃X in (1)₁Is CR, and the rest is N.

In one embodiment of the present specification, X is₁To X₃X in (1)₂Is CR, and the rest is N.

In one embodiment of the present specification, X is₁To X₃X in (1)₃Is CR, and the rest is N.

In one embodiment of the present specification, the R is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R is hydrogen, deuterium, a nitrile group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R is hydrogen, deuterium, or a nitrile group.

In one embodiment of the present specification, R is hydrogen.

In one embodiment of the present specification, the chemical formula 2 is represented by the following chemical formula 2-1.

[ chemical formula 2-1]

In the above chemical formula 2-1,

y is CR111R112, O or S,

r111, R112, R3-2 and R3-3, which may be the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the following chemical formula 4, or combine with each other to form a hydrocarbon ring,

l31 and L32, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

a32 is an integer from 0 to 8,

b33 is an integer from 0 to 8,

a33 and b33 are each plural, and the substituents in parentheses are the same as or different from each other,

n33 is 0 or 1 and,

when n33 is 0, hydrogen is bonded to each of the 2 benzene rings bonded to Y.

In one embodiment of the present specification, a33 is 0. When a33 is 0, the position capable of being substituted by R3-2 is substituted by hydrogen.

In one embodiment of the present specification, b33 is 0. When b33 is 0, the position capable of being substituted with R3-3 is substituted with hydrogen.

In one embodiment of the present specification, Y is O or S.

In one embodiment of the present specification, R3-2 is hydrogen.

In one embodiment of the present specification, R3-3 is hydrogen.

In one embodiment of the present specification, a33 is 1.

In one embodiment of the present specification, b33 is 1.

In one embodiment of the present specification, R3-2 is represented by

chemical formula

6 or 7.

In one embodiment of the present specification, R3-3 is represented by the following

chemical formula

6 or 7.

[ chemical formula 6]

[ chemical formula 7]

In the above-described

chemical formulas

6 and 7,

the dotted line is a site connected to the nucleus,

l4 and L5, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar5 and Ar6, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

c and d are integers of 0 to 5,

when c and d are plural, the substituents in parentheses may be the same or different from each other.

In one embodiment of the present specification, R3-2 and R3-3, which may be the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, the above chemical formula 4, the above chemical formula 6, or the above chemical formula 7.

In one embodiment of the present specification, R3-2 and R3-3, which may be the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, the above chemical formula 4, the above chemical formula 6, or the above chemical formula 7.

In one embodiment of the present specification, the substituent other than the substituent of the above chemical formula 4, the above chemical formula 6 or the above chemical formula 7 in the above R3-2 and R3-3 is methyl, tert-butyl, phenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, quinazolinyl, quinolyl, quinoxalyl, triphenylene, and the above phenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, quinazolinyl, quinolyl, quinoxalyl, triphenylene is substituted or unsubstituted with any one or more substituents selected from deuterium, CN, alkyl, aryl and heteroaryl.

In one embodiment of the present specification, a33 represents 2, and R3-2 represents the same or different from each other.

In one embodiment of the present specification, b33 represents 2, and R3-3 represents the same or different from each other.

In one embodiment of the present disclosure, the substituent other than the substituent of chemical formula 4, chemical formula 6 or chemical formula 7 in the plurality of R3-2 is methyl, tert-butyl, phenyl, naphthyl, pyridyl, pyrimidyl, triazinyl, quinazolinyl, quinolyl, quinoxalyl or triphenylene, and the phenyl, naphthyl, pyridyl, pyrimidyl, triazinyl, quinazolinyl, quinolyl, quinoxalyl or triphenylene is substituted or unsubstituted with any one or more substituents selected from deuterium, CN, alkyl, aryl and heteroaryl.

In one embodiment of the present disclosure, the substituent other than the substituent of chemical formula 4, chemical formula 6 or chemical formula 7 in the plurality of R3-3 is methyl, tert-butyl, phenyl, naphthyl, pyridyl, pyrimidyl, triazinyl, quinazolinyl, quinolyl, quinoxalyl or triphenylene, and the phenyl, naphthyl, pyridyl, pyrimidyl, triazinyl, quinazolinyl, quinolyl, quinoxalyl or triphenylene is substituted or unsubstituted with any one or more substituents selected from deuterium, CN, alkyl, aryl and heteroaryl.

In one embodiment of the present specification, L is₁To L₅The same or different from each other, each independently is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.

In one embodiment of the present specification, L is₁To L₅The same or different from each other, and each independently 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.

In one embodiment of the present specification, L is₁To L₅The same or different from each other, each independently is a direct bond, phenylene, 2-valent biphenyl, 2-valent terphenyl, 2-valent fluorenyl, 2-valent thiophene

Azinyl, 2-valent naphthyl, 2-valent quinazolinyl, 2-valent quinolyl, 2-valent quinoxalinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent carbazolyl, 2-valent benzocarbazolyl, 2-valent indenocarbazolyl, 2-valent phenothiazinyl, 2-valent phenoxazine

A thienyl group, a 2-valent dibenzothiapyrrolyl group, a 2-valent pyrrolyl group, a 2-valent furyl group, a 2-valent thienyl group, a 2-valent pyridyl group, a 2-valent pyrimidinyl group, or a 2-valent triazinyl group,

the phenylene group, biphenyl group having a valence of 2, terphenyl group having a valence of 2, fluorenyl group having a valence of 2, and thiophene group having a valence of 2

The thienyl group, the dibenzosilolyl group having a valence of 2, the pyrrolyl group having a valence of 2, the furyl group having a valence of 2, the thienyl group having a valence of 2, the pyridyl group having a valence of 2, the pyrimidinyl group having a valence of 2, or the triazinyl group having a valence of 2 may be substituted or unsubstituted with CN, an alkyl group having a carbon number of 1 to 10, an aryl group having a carbon number of 6 to 20, or a heteroaryl group having a carbon number of 3 to 30.

The thienyl, 2-valent dibenzothiapyrrolyl, 2-valent pyrrolyl, 2-valent furyl, 2-valent thienyl, 2-valent pyridyl, 2-valent pyrimidinyl, or 2-valent triazinyl group may be substituted or unsubstituted with CN, methyl, butyl, tert-butyl, phenyl, naphthyl, biphenyl, or terphenyl group.

Azinyl, naphthyl having a valence of 2, quinazolinyl having a valence of 2, quinolyl having a valence of 2, quinoxalinyl having a valence of 2, dibenzofuranyl having a valence of 2, dibenzothienyl having a valence of 2, carbazolyl having a valence of 2, benzocarbazolyl having a valence of 2, indenocarbazolyl having a valence of 2, and carbazolyl having a valence of 2Phenothiazinyl, 2-valent thiophene

A thienyl group, a 2-valent dibenzothiapyrrolyl group, a 2-valent pyrrolyl group, a 2-valent furyl group, a 2-valent thienyl group, a 2-valent pyridyl group, a 2-valent pyrimidyl group or a 2-valent triazinyl group, the above-mentioned phenylene group, a 2-valent biphenyl group, a 2-valent terphenyl group, a 2-valent fluorenyl group, a 2-valent thiophene group

The thienyl, 2-valent dibenzothiapyrrolyl, 2-valent pyrrolyl, 2-valent furyl, 2-valent thienyl, 2-valent pyridyl, 2-valent pyrimidyl or 2-valent triazinyl group may be overlapped with any 2 or more

The structure of (a) is present within the compound.

In the present specification, an overlapping structure means that 2 or more substituents are bonded in sequence. For example, "phenylene overlaps with 2-valent carbazolyl" means that-phenylene-2-valent carbazolyl-is bonded in this order.

In one embodiment of the present specification, L is₁To L₃The same or different from each other, and each independently is a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.

In one embodiment of the present specification, L is₁To L₃Is a direct bond.

In one embodiment of the present specification, L is₁To L₃Identical to or different from each other, each independently is a direct bond, phenylene, biphenyl having a valence of 2, or tris having a valence of 2Biphenyl, 2-valent naphthyl, 2-valent quinazolinyl, 2-valent quinolyl, 2-valent quinoxalinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent carbazolyl, 2-valent dibenzothiapyrrolyl, 2-valent pyrrolyl, 2-valent furanyl, 2-valent thienyl, or 2-valent pyridyl.

In one embodiment of the present specification, L is₃Is a direct bond, phenylene, biphenyl group having a valence of 2, terphenyl group having a valence of 2, naphthyl group having a valence of 2, quinazolinyl group having a valence of 2, quinolyl group having a valence of 2, quinoxalinyl group having a valence of 2, dibenzofuranyl group having a valence of 2, dibenzothienyl group having a valence of 2, carbazolyl group having a valence of 2, dibenzothiapyrrolyl group having a valence of 2, pyrrolyl group having a valence of 2, furanyl group having a valence of 2, thienyl group having a valence of 2, or pyridyl group having a valence of 2.

In one embodiment of the present specification, L is₃Is a direct bond or a phenylene group.

In one embodiment of the present specification, L31 and L32, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, L31 and L32 which may be the same or different from each other, are each independently 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.

In one embodiment of the present specification, L31 and L32, which may be the same or different from each other, are each independently a direct bond, phenylene, 2-valent biphenyl, 2-valent terphenyl, 2-valent fluorenyl, 2-valent thiophene

A thia group,A 2-valent dibenzothiapyrrolyl group, a 2-valent pyrrolyl group, a 2-valent furyl group, a 2-valent thienyl group, a 2-valent pyridyl group, a 2-valent pyrimidyl group, or a 2-valent triazinyl group,

The thienyl, the dibenzosilolyl having a valence of 2, the pyrrolyl having a valence of 2, the furyl having a valence of 2, the thienyl having a valence of 2, the pyridyl having a valence of 2, the pyrimidyl having a valence of 2, or the triazinyl having a valence of 2 may be present in the compound in any overlapping structure of 2 or more.

In one embodiment of the present specification, R3-2 and an adjacent group are bonded to each other to form a hydrocarbon ring.

In one embodiment of the present specification, R3-2 and adjacent groups are bonded to each other to form an aromatic hydrocarbon ring.

In one embodiment of the present specification, R3-2 and adjacent groups are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.

In one embodiment of the present specification, R3-3 and an adjacent group are bonded to each other to form a hydrocarbon ring.

In one embodiment of the present specification, R3-3 and adjacent groups are bonded to each other to form an aromatic hydrocarbon ring.

In one embodiment of the present specification, R3-3 and adjacent groups are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.

In one embodiment of the present specification, the chemical formula 2-1 is represented by any one of the following chemical formulae 2-2 to 2-6.

[ chemical formula 2-2]

[ chemical formulas 2-3]

[ chemical formulas 2-4]

[ chemical formulas 2 to 5]

In the above chemical formulas 2-2 to 2-6, R3-2, L32 and a33 are the same as defined in the above chemical formula 2-1,

r3-4 and R3-5 are the same as R3-3 of the above chemical formula 2-1,

a34 and a35 are the same as a33 of the above chemical formula 2-1.

In one embodiment of the present specification, when n is 0, one of the substituents of R3-2 and R3-3 other than the substituent of chemical formula 4 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, when the number is 0, one of the substituents of R3-2 and R3-3, which is not represented by the formula 4, is a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted benzofluorenyl group.

In one embodiment of the present specification, when 0 is mentioned above, one of the substituents other than the substituent of chemical formula 4 in R3-2 and R3-3 is a fluorenyl group substituted or unsubstituted with deuterium, an alkyl group or an alkylaryl group; or benzofluorenyl substituted or unsubstituted with deuterium, alkyl or alkylaryl.

In one embodiment of the present specification, R3-4 and R3-5 are hydrogen.

In one embodiment of the present specification, the values a34 and a35 are 0.

In one embodiment of the present specification, Ar is₄₁And Ar₄₂Identical to or different from each other, each independently is methyl; a silyl group; a phenyl group; biphenyl radical(ii) a A naphthyl group; a terphenyl group; a dibenzofuranyl group; a dibenzothienyl group; a carbazolyl group; a silole group; or polycyclic heteroaryl containing Si, N, O or S,

the above methyl group; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; a dibenzofuranyl group; a dibenzothienyl group; a carbazolyl group; a silole group; or a polycyclic heteroaryl group containing Si, N, O, or S is substituted or unsubstituted with deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

In one embodiment of the present specification, Ar is₄₁And Ar₄₂Identical to or different from each other, each independently is methyl; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; a dibenzofuranyl group; a dibenzothienyl group; a carbazolyl group; a silole group; or polycyclic heteroaryl containing Si, N, O or S,

the above methyl group; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; a dibenzofuranyl group; a dibenzothienyl group; a carbazolyl group; a silole group; or a polycyclic heteroaryl group containing Si, N, O, or S is substituted or unsubstituted with one or more substituents selected from deuterium, a nitrile group, a halogen group, a substituted or unsubstituted methyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzocarbazolyl group, and a substituted or unsubstituted pyridyl group.

In one embodiment of the present specification, Ar5 and Ar6, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each is independently a methyl group; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; a dibenzofuranyl group; a dibenzothienyl group; a carbazolyl group; a silole group; or polycyclic heteroaryl containing Si, N, O or S,

the above methyl group; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; a dibenzofuranyl group; a dibenzothienyl group; a carbazolyl group; a silole group; or a polycyclic heteroaryl group containing Si, N, O, or S is substituted or unsubstituted with deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group of 10 carbon atoms of 1, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group of 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group of 3 to 20 carbon atoms.

In one embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each is independently a methyl group; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; a dibenzofuranyl group; a dibenzothienyl group; a carbazolyl group; a silole group; or tricyclic heteroaryl containing Si, N, O or S,

the above methyl group; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; a dibenzofuranyl group; a dibenzothienyl group; a carbazolyl group; a silole group; or a tricyclic heteroaryl group containing Si, N, O or S is substituted or unsubstituted with one or more substituents selected from deuterium, a nitrile group, a halogen group, methyl, trifluoromethyl, trifluoromethoxy, methoxy, trimethylsilyl, phenyl, biphenyl, terphenyl, naphthyl, carbazolyl substituted with phenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, indolocarbazolyl, pyridyl.

In one embodiment of the present specification, Ar5 and Ar6 may be the same as or different from each other, and each is independently Ar₄₁And Ar₄₂Identical to or different from each other, each independently is methyl, ethyl, butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, perylene, fluorenyl, fluorenylxanthenyl, carbazolyl, benzocarbazolyl, indenocarbazolyl, pyridyl, pyrimidyl, triazinyl, dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl, thiophene

Oxazinyl, phenothiazinyl having a valence of 2, thiophene having a valence of 2

A thiayl group, or a trimethylsilyl group,

Oxazinyl, phenothiazinyl having a valence of 2, or thiophene having a valence of 2

Selected as the thiayl groupAny one or more of the group consisting of deuterium, CN, methyl, tert-butyl, phenyl substituted with a methyl group, trifluoromethyl, trifluoromethoxy, pyridyl, pyrimidyl, triazinyl, dibenzofuranyl, dibenzothienyl, trimethylsilyl, triphenylsilyl, and carbazolyl is substituted or unsubstituted.

In one embodiment of the present specification, the chemical formula 2 is any one of the following compounds.

In one embodiment of the present specification, the chemical formula 2 is any one of compounds shown in the following table. In the following table, the dotted line represents the position bonded to chemical formula 4.

According to an embodiment of the present invention, the compound of chemical formula 1 may be produced as shown in the following reaction formula 1, and the compound of chemical formula 2 may be produced as shown in the following reaction formula 2. The following

reaction formulae

1 and 2 describe the synthesis process of a part of the compounds corresponding to the

chemical formulae

1 and 2 of the present application, but various compounds corresponding to the

chemical formulae

1 and 2 of the present application can be synthesized by the synthesis process shown in the following

reaction formulae

1 and 2, substituents can be bonded by a method known in the art, and the kind, position and number of substituents can be changed according to the techniques known in the art.

[ reaction formula 1]

[ reaction formula 2]

In the above reaction formula 1, R means a substituent attached to the nucleus, and may be R1 to R3, B1 or B2 of the present invention, and the remaining substituents are as defined above. In the above reaction formula 2, the substituents are as defined above, and can be synthesized by a general coupling reaction. For example, the resin can be produced by Suzuki coupling reaction or the like.

The organic light emitting device of the present specification may be manufactured using a general method and material for manufacturing an organic light emitting device, in addition to forming the first organic layer using the compound represented by the above chemical formula 1 and forming the second organic layer using the compound represented by the above chemical formula 2.

The first organic layer including the compound represented by chemical formula 1 and the second organic layer including the compound represented by chemical formula 2 may be formed by a solution coating method as well as a vacuum evaporation method. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic layer of the organic light emitting device of the present specification may be composed of a structure including only the first organic layer and the second organic layer described above, but may also be composed of a structure further including an additional organic layer. The additional organic layer may be 1 or more layers selected from a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection, and a hole blocking layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller or greater number of organic layers may be included.

In the organic light emitting device according to one embodiment of the present specification, the first electrode is an anode, the second electrode is a cathode, the first organic layer is a light emitting layer, and the second organic layer is provided between the second electrode and the first organic layer. That is, the second organic layer is provided between the cathode and the light-emitting layer. In an organic light-emitting device according to an embodiment of the present specification, the first organic layer is a light-emitting layer.

In the organic light emitting device according to one embodiment of the present specification, the first organic layer is a light emitting layer, and the compound represented by the chemical formula 1 is included as a dopant of the light emitting layer.

In the organic light emitting device according to one embodiment of the present specification, the first organic layer is a light emitting layer, and the compound represented by the chemical formula 1 is used as a dopant of the light emitting layer and further includes a fluorescent host or a phosphorescent host. At this time, the dopant in the light emitting layer may be included at 1 to 50 parts by weight, preferably, 0.1 to 30 parts by weight, and more preferably, 1 to 10 parts by weight with respect to 100 parts by weight of the host. When within the above range, energy transfer from the host to the dopant occurs efficiently.

In one embodiment of the present specification, the host is an anthracene derivative.

In one embodiment of the present disclosure, the organic layer includes 2 or more light emitting layers, and 1 of the 2 or more light emitting layers includes the compound represented by chemical formula 1.

In one embodiment of the present specification, the maximum emission peaks of the 2 or more light-emitting layers are different from each other. The light emitting layer including the compound represented by the above chemical formula 1 is blue, and the light emitting layer not including the compound represented by the above chemical formula 1 may include a blue, red or green light emitting compound known in the art.

In one embodiment of the present disclosure, the light emitting layer including the compound represented by chemical formula 1 includes a fluorescent dopant, and the light emitting layer not including the compound represented by chemical formula 1 includes a phosphorescent dopant.

In one embodiment of the present specification, the maximum emission peak of the light emitting layer including the compound represented by the above chemical formula 1 is 400nm to 500 nm. That is, the light emitting layer including the compound represented by the above chemical formula 1 emits blue light.

The organic layer of the organic light emitting device according to an embodiment of the present specification includes 2 or more light emitting layers, the maximum light emission peak of one light emitting layer (light emitting layer 1) is 400nm to 500nm, and the maximum light emission peak of the other light emitting layer (light emitting layer 2) may show a maximum light emission peak of 510nm to 580nm, or 610nm680 nm. At this time, the light emitting layer 1 includes the compound represented by the above chemical formula 1.

In an organic light emitting device according to an embodiment of the present specification, the second organic layer is an electron transporting region. Specifically, the second organic layer includes 1 or more layers selected from a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.

In an organic light emitting device according to another embodiment, the second organic layer includes 1 or 2 layers selected from a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.

In an organic light emitting device according to another embodiment, the second organic layer is a hole blocking layer, an electron transporting layer, an electron injecting layer, or an electron injecting and transporting layer.

In an organic light emitting device according to another embodiment, the second organic layer is a hole blocking layer.

In an organic light emitting device according to another embodiment, the second organic layer is an electron transport layer.

In an organic light emitting device according to another embodiment, the second organic layer is an electron injection and transport layer.

In an organic light emitting device according to another embodiment, the second organic layer includes a hole blocking layer, and an electron injection and transport layer. In this case, the hole blocking layer is provided in contact with the light-emitting layer, and the electron injection and transport layer is provided in contact with the cathode.

In one embodiment of the present disclosure, the second organic layer is provided in contact with the first organic layer.

In one embodiment of the present specification, the second organic layer further contains 1 or 2 or more n-type dopants selected from alkali metals and alkaline earth metals.

When the organic alkali metal compound or the organic alkaline earth metal compound is used as an n-type dopant, stability of holes in the light-emitting layer can be ensured, and thus the lifetime of the organic light-emitting device can be improved. In addition, the electron mobility of the electron transport layer, and the proportion of the organic alkali metal compound or the organic alkaline earth metal compound are adjusted to maximize the balance of holes and electrons in the light emitting layer, so that the light emitting efficiency can be increased.

In this specification, LiQ is more preferable as the n-type dopant used for the second organic layer.

The second organic layer may include the compound of chemical formula 2 and the n-type dopant at a weight ratio of 1:9 to 9: 1. Preferably, the compound of the above chemical formula 2 and the above n-type dopant may be contained at 2:8 to 8:2, and more preferably, may be contained at 3:7 to 7: 3.

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

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

In one embodiment of the present specification, the organic light-emitting device may have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present disclosure, the organic light emitting device may have a reverse structure (inverted type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.

The structure of the organic light emitting device of the present specification may have the structure shown in fig. 1,2, and 8, but is not limited thereto.

Fig. 1 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the light emitting layer 6, and the compound represented by the above chemical formula 2 may be contained in the hole blocking layer 7 or the electron injection and transport layer 8.

Fig. 2 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the light emitting layer 6, and the compound represented by the above chemical formula 2 may be contained in the electron injecting and transporting layer 8.

Fig. 8 illustrates a substrate 1 stacked in this order; an anode 2; a p-doped hole transport layer 4p,

hole transport layers

4R, 4G, 4B; light-emitting layers 6RP, 6GP, 6 BF; a first electron transport layer 9 a; a second electron transport layer 9 b; an electron injection layer 10; cathode 11 and capping layer 14. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the light emitting layers 6RP, 6GP, 6BF, and the compound represented by the above chemical formula 2 may be contained in 1 or more layers among the first electron transport layer 9a, the second electron transport layer 9b and the electron injection layer 10.

According to an embodiment of the present disclosure, the organic light emitting device may have a series structure in which two or more independent devices are connected in series. In one embodiment, the series structure may be a structure in which the respective organic light emitting devices are bonded to each other by a charge generation layer. The device having the series structure can be driven at a lower current than the unit device with the same luminance as a reference, and therefore, the device has an advantage that the lifetime characteristics are greatly improved.

According to an embodiment of the present disclosure, the organic layer includes: the light-emitting device includes a first stack including 1 or more light-emitting layers, a second stack including 1 or more light-emitting layers, and 1 or more charge generation layers provided between the first stack and the second stack.

According to an embodiment of the present disclosure, the organic layer includes: a first stacked body including 1 or more light emitting layers; a second stacked body including 1 or more light emitting layers; and a third stacked body including 1 or more light emitting layers, each of which includes 1 or more charge generation layers between the first stacked body and the second stacked body and between the second stacked body and the third stacked body.

In the present specification, a Charge Generating layer (Charge Generating layer) refers to a layer that generates holes and electrons when a voltage is applied. The charge generation layer may be an N-type charge generation layer or a P-type charge generation layer. In this specification, the N-type charge generation layer refers to a charge generation layer closer to the anode than the P-type charge generation layer, and the P-type charge generation layer refers to a charge generation layer closer to the cathode than the N-type charge generation layer.

The N-type charge generation layer and the P-type charge generation layer may be disposed in contact with each other, and thus, an NP junction is formed. Holes are easily formed in the P-type charge generation layer and electrons are easily formed in the N-type charge generation layer by the NP junction. Electrons are transported in the anode direction by the LUMO level of the N-type charge generation layer, and holes are transported in the cathode direction by the HOMO level of the P-type organic layer.

The above-described first stack, second stack, and third stack each include 1 or more light-emitting layers, and may further include 1 or more layers of a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, a layer which performs both hole transport and hole injection (a hole injection and transport layer), and a layer which performs both electron transport and electron injection (an electron injection and transport layer).

An organic light emitting device including the above-described first stack body and second stack body is illustrated in fig. 3.

Fig. 3 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first light emitting layer 6a, a first electron transport layer 9a, an N-type charge generation layer 12, a P-type charge generation layer 13, a second hole transport layer 4b, a second light emitting layer 6b, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the first light emitting layer 6a or the second light emitting layer 6b, and the compound represented by the above chemical formula 2 may be contained in the first electron transporting layer 9a or the electron injecting and transporting layer 8.

Organic light emitting devices including the above-described first to third stacks are illustrated in fig. 4 to 7.

Fig. 4 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first light emitting layer 6a, a first electron transport layer 9a, a first N-type charge generation layer 12a, a first P-type charge generation layer 13a, a second hole transport layer 4b, a second light emitting layer 6b, a second electron transport layer 9b, a second N-type charge generation layer 12b, a second P-type charge generation layer 13b, a third hole transport layer 4c, a third light emitting layer 6c, a third electron transport layer 9c, and a cathode 11 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 may be included in the first, second, and third

light emitting layers

6a, 6b, and 6c, and the compound represented by the above chemical formula 2 may be included in 1 or more layers among the first, second, and third

electron transport layers

9a, 9b, and 9 c.

Fig. 5 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, a first electron transport layer 9a, a first N-type charge generation layer 12a, a first P-type charge generation layer 13a, a third hole transport layer 4c, a red phosphorescent light emitting layer 6RP, a yellow green phosphorescent light emitting layer 6YGP, a green phosphorescent light emitting layer 6GP, a second electron transport layer 9b, a second N-type charge generation layer 12b, a second P-type charge generation layer 13b, a fourth hole transport layer 4d, a fifth hole transport layer 4e, a second blue fluorescent light emitting layer 6BFb, a third electron transport layer 9c, an electron injection layer 10, a cathode 11, and a capping layer 14 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 may be included in the first blue fluorescent light-emitting layer 6BFa or the second blue fluorescent light-emitting layer 6BFb, and the compound represented by the above chemical formula 2 may be included in 1 or more layers among the first electron transport layer 9a, the second electron transport layer 9b, the third electron transport layer 9c, and the electron injection layer 10.

Fig. 6 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, a first electron transport layer 9a, a first N-type charge generation layer 12a, a first P-type charge generation layer 13a, a third hole transport layer 4c, a red phosphorescent light emitting layer 6RP, a green phosphorescent light emitting layer 6GP, a second electron transport layer 9b, a second N-type charge generation layer 12b, a second P-type charge generation layer 13b, a fourth hole transport layer 4d, a fifth hole transport layer 4e, a second blue fluorescent light emitting layer 6BFb, a third electron transport layer 9c, an electron injection layer 10, a cathode 11, and a cover layer 14 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 may be included in the first blue fluorescent light-emitting layer 6BFa or the second blue fluorescent light-emitting layer 6BFb, and the compound represented by the above chemical formula 2 may be included in 1 or more layers among the first electron transport layer 9a, the second electron transport layer 9b, the third electron transport layer 9c, and the electron injection layer 10.

Fig. 7 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a first P-doped hole transport layer 4pa, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, a first electron transport layer 9a, a first N-type charge generation layer 12a, a first P-type charge generation layer 13a, a third hole transport layer 4c, a fourth hole transport layer 4d, a second blue fluorescent light emitting layer 6BFb, a second electron transport layer 9b, a second N-type charge generation layer 12b, a second P-type charge generation layer 13b, a fifth hole transport layer 4e, a sixth hole transport layer 4f, a third blue fluorescent light emitting layer 6BFc, a third electron transport layer 9c, an electron injection layer 10, a cathode 11, and a capping layer 14 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 may be included in 1 or more layers among the first blue fluorescent light-emitting layer 6BFa, the second blue fluorescent light-emitting layer 6BFb, and the third blue fluorescent light-emitting layer 6BFb, and the compound represented by the above chemical formula 2 may be included in 1 or more layers among the first electron transport layer 9a, the second electron transport layer 9c, the third electron transport layer 9c, and the electron injection layer 10.

Fig. 9 illustrates an organic light-emitting device structure in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. In the structure as described above, the compound represented by the

above chemical formula

1 or 2 may be contained in the light emitting layer 6, and the compound represented by the above chemical formula 3 may be contained in the hole blocking layer 7 or the electron injection and transport layer 8.

Fig. 10 illustrates an organic light-emitting device structure in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 6, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. In the structure as described above, the compound represented by the

above chemical formula

1 or 2 may be contained in the light emitting layer 6, and the compound represented by the above chemical formula 3 may be contained in the electron injecting and transporting layer 8.

The N-type charge generation layer may be 2,3,5, 6-tetrafluoro-7, 7,8, 8-tetracyanodimethyl-p-benzoquinone (F4TCNQ), fluorine-substituted 3,4,9, 10-perylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenylamine derivatives, or the like, but is not limited thereto. In one embodiment, the N-type charge generation layer may include both a benzimidazolephenanthrene derivative and Li metal.

The P-type charge generation layer may contain both an arylamine derivative and a cyano group-containing compound.

The organic light emitting device of the present specification can be manufactured using materials and methods known in the art, except that the organic layer contains the above-described compound.

When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances. The organic light emitting device according to the present specification may be manufactured as follows: the organic el device is manufactured by forming an anode by depositing metal, a metal oxide having conductivity, or an alloy thereof on a substrate, forming an organic layer including the first organic layer and the second organic layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.

The organic layer including the above-described first organic layer and second organic layer may be a multilayer structure further including a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection and transport layer, a hole blocking layer, and the like. The organic layer can be produced as a smaller number of layers by a solvent process (solvent process) other than the vapor deposition method, for example, spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method using various polymer materials.

The anode is an electrode for injecting holes, and a substance having a large work function is generally preferable as an anode substance so that holes can be smoothly injected into the organic 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 Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO₂A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.

The cathode is an electrode for injecting electrons, and a substance having a small work function is generally preferable as a cathode substance in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO₂And a multilayer structure material such as Al, but not limited thereto.

The hole injection layer is a layer that serves to smoothly inject holes from the anode into the light-emitting layer, and has a single-layer or multilayer structure of 2 or more layers. The hole injecting substance is a substance that can receive holes from the anode well at a low voltage, and preferably a HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrine), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers. In one embodiment of the present specification, the hole injection layer has a 2-layer structure, and the respective layers contain the same or different substances from each other.

The hole transport layer may have a single-layer structure or a multilayer structure having 2 or more layers, and serves to smoothly transport holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously. In one embodiment of the present specification, the hole transport layer has a 2-layer structure, and the respective layers contain the same or different substances from each other. In one embodiment of the present invention, an arylamine compound is used as a substance of the hole transport layer.

As the above-described hole injection and transport layer as a layer for simultaneously performing hole transport and hole injection, a hole transport layer material and/or a hole injection layer material known in the art may be used.

As the above-described electron injection and transport layer as a layer for simultaneously performing electron transport and electron injection, an electron transport layer material and/or an electron injection layer material known in the art may be used.

An electron blocking layer may be provided between the hole transport layer and the light-emitting layer. The electron blocking layer may be made of a material known in the art.

The light-emitting layer may emit red, green or blue light, and may be formed of a phosphorescent substance or a fluorescent substance. The luminescent material is capable of emitting light from the spaceThe hole transport layer and the electron transport layer receive holes and electrons, respectively, and combine them to emit light in the visible light region, and preferably have high quantum efficiency with respect to fluorescence or phosphorescence. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3); a carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is

Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.

As a host material of the light-emitting layer, there are aromatic fused ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds

Pyrimidine derivatives, etc., but are not limited thereto.

When the light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent material such as piqir (acac) (bis (1-phenylisoquinoline) acetylacetonatoiridium, bis (1-phenylisoquinoline) acetylacetonatoiridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonatoiridium, bis (1-phenylquinoline) acetylacetonatoiridium), PQIr (tris (1-phenylquinoline) iridium, tris (1-phenylquinoline) iridium), PtOEP (octylporphyrin, platinum octaethylporphyrin), or Alq (r) may be used₃(tris (8-hydroxyquinolino) aluminum), etc., but is not limited thereto. When the light-emitting layer emits green light, Ir (ppy) can be used as a light-emitting dopant₃Phosphorescent substances such as fac tris (2-phenylpyridine) iridium, and Alq tris (2-phenylpyridine) iridium₃(tris (8-hydroxyquinolino) aluminum), etc., but not onlyAnd is limited thereto. When the light-emitting layer emits blue light, (4, 6-F) may be used as the light-emitting dopant₂ppy)₂Examples of the fluorescent substance include phosphorescent substances such as Irpic and fluorescent substances such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), Distyrylbenzene (DSB), Distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers, but the fluorescent substances are not limited thereto.

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

The electron transport layer functions to smooth the transport of electrons. The electron transport material is a material that can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and is preferably a material having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto.

The electron injection layer can perform a function of smoothly injecting electrons. As the electron-injecting substance, the following compounds are preferred: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect for a light-emitting layer or a light-emitting material, and having an excellent thin film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,

Azole,

Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.

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

Modes for carrying out the invention

Hereinafter, in order to specifically explain the present specification, the details will be explained by referring to examples, comparative examples, and the like. However, the examples and comparative examples according to the present specification may be modified into various forms, and the scope of the present specification is not to be construed as being limited to the examples and comparative examples described in detail below. The examples and comparative examples of the present specification are provided to more fully describe the present specification to those skilled in the art.

PREPARATION EXAMPLE 1 Synthesis of Compound 1

1) Synthesis of intermediate 1

Under a nitrogen atmosphere, 100g of 1-bromo-2,3-dichloro-5-methylbenzene [1-bromo-2, 3-dichloro-5-methylbenezene ]]117g of amine A-1, 60g of sodium tert-butoxide (sodium tert-butoxide), 2.1g of bis (tri-tert-butylphosphine) palladium (0) (Pd (P (t-Bu)₃)₂) After addition to 3.0L of toluene, it was heated and stirred at 120 ℃ for 2 hours. After the reaction is finished, cooling the reaction liquid to room temperature, adding water and NH₄Cl, after separation, MgSO₄(anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 130g of intermediate 1 (yield 82%, Mass (Mass) [ M +)]＝441)。

2) Synthesis of intermediate 2

Under a nitrogen atmosphere, 30g of intermediate 1, 28g of Compound A-2, 9.8g of sodium tert-butoxide, 0.7g of bis (tri-tert-butylphosphino) palladium (0) (Pd (P (t-Bu)₃)₂) After addition to 550mL of toluene, the mixture was heated and stirred at 150 ℃ for 8 hours. After the reaction is finished, cooling the reaction liquid to room temperature, adding water and NH₄Cl, after separation, MgSO₄(anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 42g of intermediate 2 (yield 76%, mass [ M + ])]＝810)。

3) Synthesis of Compound 1

To a flask containing 42g of intermediate 2 dissolved in 400mL of toluene (anhydrous) cooled to 0 ℃ was slowly added dropwise 122mL of t-butyllithium (t-BuLi (1.7M in pentane)) under a nitrogen atmosphere, followed by stirring at 60 ℃ for 3 hours. When the lithium-halogen exchange reaction is finished, the solution is cooled to 0 ℃ again, and 7.5mL of boron tribromide (BBr) is slowly added dropwise₃) Then, the temperature was raised to 70 ℃ and the mixture was stirred for 10 hours. After the reaction is finished, cooling the reaction liquid to room temperature, adding water and NH₄Cl, after separation, MgSO₄(anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane), whereby 9.5g of compound 1 (yield 23%, mass [ M +) was obtained]＝783)。

PREPARATION EXAMPLE 2 Synthesis of Compound 2

1) Synthesis of intermediate 3

Under a nitrogen atmosphere, 20g of 2-bromo-1,3-diiodo-5-methylbenzene [2-bromo-1, 3-diiodo-5-methylbenezene]38g of amine A-2, 14g of sodium tert-butoxide, 0.24g of bis (tri-tert-butylphosphine) palladium (0) (Pd (P (t-Bu)₃)₂) Added to 450mL of tolueneAfter neutralization, the mixture was heated and stirred at 120 ℃ for 4 hours. After the reaction is finished, cooling the reaction liquid to room temperature, adding water and NH₄Cl, after separation, MgSO₄(anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 35g of intermediate 3 (yield 76%, mass [ M + ]]＝979)。

2) Synthesis of Compound 2

To a flask containing 35g of intermediate 3 dissolved in 300mL of toluene (anhydrous) cooled to 0 ℃ was slowly dropped 35mL of n-butyllithium (n-BuLi (2.5M in hexane)), under a nitrogen atmosphere, and then stirred at 60 ℃ for 1 hour. When the lithium-halogen exchange reaction is finished, the solution is cooled to 0 ℃ again, and 5.2mL of boron tribromide (BBr) is slowly added dropwise₃) Then, the temperature was raised to 70 ℃ and stirred for 6 hours. After the reaction is finished, cooling the reaction liquid to room temperature, adding water and NH₄Cl, after separation, MgSO₄(anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane), whereby 9.0g of compound 2 was obtained (yield 34%, mass [ M +)]＝908)。

PREPARATION EXAMPLE 3 Synthesis of Compound 3

1) Synthesis of

intermediates

4 and 5

18g of intermediate 4 was obtained (yield 75%, mass [ M + ]: 579) by the same method as the method for producing intermediate 1 of production example 1, except that 18g of amine a-3 was used instead of amine a-1.

The preparation was carried out in the same manner as the preparation method of intermediate 2 of preparation example 1 except that 18g of intermediate 4 was used instead of intermediate 1 and 8.8g of amine a-1 was used instead of amine a-2, whereby 18g of intermediate 5 was obtained (yield 70%, mass [ M + ]: 824).

2) Synthesis of Compound 3

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 18g of the intermediate 5 was used instead of the intermediate 2, thereby obtaining 4.0g of the compound 3 (yield 23%, mass [ M + ]: 797).

PREPARATION EXAMPLE 4 Synthesis of Compound 4

The preparation was carried out in the same manner as in the preparation of intermediate 2 of preparation example 1 except that 9.5g of amine a-4 was used instead of amine a-2, whereby 14.5g of intermediate 6 was obtained (yield 78%, mass [ M + ]: 824).

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 14.5g of the intermediate 6 was used instead of the intermediate 2, whereby 3.1g of the compound 4 was obtained (yield 22%, mass [ M + ]: 797).

PREPARATION EXAMPLE 5 Synthesis of Compound 5

1) Synthesis of intermediate 7

An amination reaction was carried out in the same manner as in the production method of intermediate 1 of production example 1 except that 20g of 3-bromo-4,5-dichlorophenol [3-bromo-4,5-dichlorophenol ] was used instead of 1-bromo-2,3-dichloro-5-methylbenzene, and then the following reaction was carried out without purification.

After dissolving the amination product in 420mL of Dimethylformamide (DMF), 34g of potassium carbonate (potassium carbonate) was added at room temperature, and 22mL of perfluorobutanesulfonyl fluoride was added dropwise at 0 deg.C[perfluorobutanesulfonyl floride]. After the reaction was completed, 400mL of water and 200mL of ethyl acetate were added and the mixture was stirred for 30 minutes. The organic layer was washed 2 times with NaCl solution (aq. Recovering the separated organic layer with Mg₂SO₄(anhydrous) treatment and filtration. The solvent of the filtered solution was distilled off under reduced pressure and purified by recrystallization (ethyl acetate/hexane) to obtain 40g of intermediate 7 (yield 77%, mass [ M +)]＝725)。

2) Synthesis of intermediate 8

The reaction mixture was charged with 20g of intermediate 7, 4.7g of amine A-5, 0.16g of tris (dibenzylideneacetone) dipalladium (0) [ Palladium (0) bis (dibenzylideneacetone ]](Pd(dba)₂) A flask of 0.26g of 2-dicyclohexylphospho-2 ',4',6'-triisopropylbiphenyl (2-Dicyclohexylphosphino-2',4',6' -triisopropylphenyl) (Xphos), 18g of cesium carbonate (ceium carbonate) and 300mL of xylene was heated and stirred at 130 ℃ for 12 hours. Cooling the reaction solution to room temperature, and adding NH₄Saturated solution of Cl (sat. aq. NH)₄Cl) and xylene, and after separation, the solvent was distilled off under reduced pressure. Purification by column chromatography (ethyl acetate/hexane) gave 13g of intermediate 8 (yield 77%, mass [ M +)]＝594)。

3) Synthesis of intermediate 9

17g of intermediate 9 (yield 81%, mass [ M + ]: 963) was obtained by performing the production in the same manner as in the production method of intermediate 2 of production example 1, except that 13g of intermediate 8 was used instead of intermediate 1.

4) Synthesis of Compound 5

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 17g of the intermediate 9 was used instead of the intermediate 2, whereby 3.5g of the compound 5 was obtained (yield 21%, mass [ M + ] ═ 937).

PREPARATION EXAMPLE 6 Synthesis of Compound 6

15g of intermediate 10 (yield 75%, mass [ M + ]: 886) was obtained by performing the production in the same manner as in the production method of intermediate 2 of production example 1, except that 11g of amine a-6 was used instead of amine a-2.

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 15g of the intermediate 10 was used instead of the intermediate 2, whereby 3.0g of the compound 6 was obtained (yield 21%, mass [ M + ]: 860).

PREPARATION EXAMPLE 7 Synthesis of Compound 7

The preparation was carried out in the same manner as in the preparation of intermediate 2 of preparation example 1 except that 9.7g of a-7 was used instead of amine a-2, whereby 13g of intermediate 11 was obtained (yield 69%, mass [ M + ]: 830).

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 5.0g of the intermediate 11 was used instead of the intermediate 2, whereby 3.0g of the compound 7 was obtained (yield 24%, mass [ M + ] ═ 804).

PREPARATION EXAMPLE 8 Synthesis of Compound 8

The preparation was carried out in the same manner as the preparation of intermediate 2 of preparation example 1 except that 14g of a-8 was used instead of amine a-2, whereby 20g of intermediate 12 was obtained (yield 72%, mass [ M + ]: 820).

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 20g of the intermediate 12 was used instead of the intermediate 2, whereby 4.2g of the compound 8 was obtained (yield 22%, mass [ M + ]: 792).

PREPARATION EXAMPLE 9 Synthesis of Compound 9

The preparation was carried out in the same manner as the preparation of intermediate 8 of preparation example 5 except that 14g of a-9 was used instead of amine a-5, thereby obtaining 16g of intermediate 13 (yield 68%, mass [ M + ]: 853).

18g of intermediate 14 (yield 78%, mass [ M + ]: 1222) was obtained by performing the production in the same manner as the production method of intermediate 2 of production example 1, except that 16g of intermediate 13 was used instead of intermediate 1.

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 18g of the intermediate 14 was used instead of the intermediate 2, whereby 3.6g of the compound 9 was obtained (yield 20%, mass [ M + ]: 1195).

PREPARATION EXAMPLE 10 Synthesis of Compound 10

43g of intermediate 15 (yield 77%, mass [ M + ]: 824) was obtained by the same method as the method for producing intermediate 2 of production example 1, except that 28g of a-10 was used instead of amine a-2.

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 43g of the intermediate 15 was used instead of the intermediate 2, thereby obtaining 8.9g of the compound 10 (yield 21%, mass [ M + ]: 797).

PREPARATION EXAMPLE 11 Synthesis of Compound 11

The preparation was carried out in the same manner as the preparation of intermediate 2 of preparation example 1 except that 29g of a-11 was used instead of amine a-2, whereby 41g of intermediate 16 was obtained (yield 72%, mass [ M + ]. 834).

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 41g of the intermediate 16 was used instead of the intermediate 2, whereby 6.7g of the compound 11 was obtained (yield 17%, mass [ M + ]: 807).

PREPARATION EXAMPLE 12 Synthesis of Compound 12

18g of intermediate 17 (yield 76%, mass [ M + ]. 565) was obtained by the same method as the method for producing intermediate 1 of production example 1, except that 17g of a-2 was used instead of amine a-1.

The production was carried out in the same manner as the production method of intermediate 2 of production example 1 except that 18g of intermediate 17 was used instead of intermediate 1 and 17g of a-12 was used instead of amine a-2, whereby 24g of intermediate 18 was obtained (yield 72%, mass [ M + ]: 1046).

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 24g of the intermediate 18 was used instead of the intermediate 2, whereby 5.1g of the compound 12 was obtained (yield 22%, mass [ M + ]: 1020).

PREPARATION EXAMPLE 13 Synthesis of Compound 13

13g of intermediate 19 (yield 71%, mass [ M + ] ═ 444) was obtained by the same method as the method for producing intermediate 1 of production example 1, except that 5.0g of 1-bromo-2,3-dichloro-5- (methyl-d 3) -benzene was used instead of 1-bromo-2, 3-dichloro-5-methylbenzene.

The preparation was carried out in the same manner as in the preparation of intermediate 2 of preparation example 1 except that 13g of intermediate 19 was used instead of intermediate 1 and 8.8g of a-13 was used instead of amine a-2, whereby 14g of intermediate 20 was obtained (yield 67%, mass [ M + ]: 709).

The preparation was carried out in the same manner as the preparation method of the compound 1 in the preparation example 1 except that 14g of the intermediate 20 was used instead of the intermediate 2, whereby 3.4g of the compound 13 was obtained (yield 25%, mass [ M + ] ═ 682).

PREPARATION EXAMPLE 14 Synthesis of Compound 14

The preparation was carried out in the same manner as in the preparation of intermediate 8 of preparation example 5 except that 6.2g of a-14 was used instead of amine a-5, whereby 13g of intermediate 21 was obtained (yield 72%, mass [ M + ]: 650).

The preparation was carried out in the same manner as in the preparation of intermediate 2 of preparation example 1 except that 16g of intermediate 21 was used instead of intermediate 1 and 11g of a-15 was used instead of amine a-2, whereby 18g of intermediate 22 was obtained (yield 77%, mass [ M + ] ═ 1172).

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 18g of the intermediate 22 was used instead of the intermediate 2, whereby 4.0g of the compound 14 was obtained (yield 23%, mass [ M + ]: 1145).

PREPARATION EXAMPLE 15 Synthesis of Compound 15

14g of intermediate 23 was obtained (yield 73%, mass [ M + ]. 840) by the same method as the method for producing intermediate 2 of production example 1, except that 9.9g of a-16 was used instead of amine a-2.

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 14g of the intermediate 23 was used instead of the intermediate 2, thereby obtaining 2.7g of the compound 15 (yield 20%, mass [ M + ]: 814).

PREPARATION EXAMPLE 16 Synthesis of Compound 16

The preparation was carried out in the same manner as in the preparation of intermediate 2 of preparation example 1 except that 13.3g of a-17 was used instead of amine a-2, whereby 15g of intermediate 24 was obtained (yield 67%, mass [ M + ]: 989).

The preparation was carried out in the same manner as the preparation method of compound 1 in preparation example 1 except that 15g of intermediate 24 was used instead of intermediate 2, whereby 3.0g of compound 16 was obtained (yield 21%, mass [ M + ]: 963).

PREPARATION EXAMPLE 17 Synthesis of Compound 17

The preparation was carried out in the same manner as in the preparation of intermediate 2 of preparation example 1 except that 17.1g of a-18 was used instead of amine a-2, whereby 20g of intermediate 25 was obtained (yield 65%, mass [ M + ]: 908).

The preparation was carried out in the same manner as in the preparation of compound 1 of preparation example 1 except that 20g of intermediate 25 was used instead of intermediate 2, whereby 4.1g of compound 17 was obtained (yield 21%, mass [ M + ] ═ 882).

PREPARATION EXAMPLE 18 Synthesis of Compound 18

14g of intermediate 26 (yield 66%, mass [ M + ]. 938) was obtained by the same method as the method for producing intermediate 2 of production example 1, except that 12.g of a-19 was used instead of amine a-2.

The preparation was carried out in the same manner as the preparation method of compound 1 in preparation example 1 except that 14g of intermediate 26 was used instead of intermediate 2, whereby 2.9g of compound 18 was obtained (yield 21%, mass [ M + ] ═ 912).

PREPARATION EXAMPLE 19 Synthesis of Compound 19

19g of intermediate 27 (yield 62%, mass [ M + ]: 911) was obtained by performing the production in the same manner as in the production method of intermediate 20 of production example 13, except that 17g of a-20 was used instead of amine a-13.

The preparation was carried out in the same manner as in the preparation of compound 13 of preparation example 13, except that 19g of intermediate 27 was used instead of intermediate 20, whereby 3.6g of compound 19 was obtained (yield 20%, mass [ M + ] ═ 885).

PREPARATION EXAMPLE 20 Synthesis of Compound 20

13g of intermediate 28 (yield 76%, mass [ M + ]. 483) was obtained by the same method as the method for producing intermediate 1 of production example 1, except that 10g of 1-bromo-2, 3-dichloro-5-tert-butylbenzene was used instead of 1-bromo-2, 3-dichloro-5-methylbenzene.

Production was carried out in the same manner as the production method of intermediate 2 of production example 1 except that 13g of intermediate 28 was used instead of intermediate 1 and 14g of a-18 was used instead of amine a-2, whereby 18g of intermediate 29 was obtained (yield 70%, mass [ M + ]: 950).

The preparation was carried out in the same manner as the preparation method of the compound 1 of the preparation example 1 except that 18g of the intermediate 29 was used instead of the intermediate 2, whereby 3.4g of the compound 20 was obtained (yield 19%, mass [ M + ]: 924).

PREPARATION EXAMPLE 21 Synthesis of Compound 21

Production was carried out in the same manner as the production method of intermediate 1 of production example 1 except that 11g of a-21 was used instead of a-1, thereby obtaining 12g of intermediate 30 (yield 70%, mass [ M + ]: 413).

The production was carried out in the same manner as the production method of intermediate 2 of production example 1 except that 12g of intermediate 30 was used instead of intermediate 1 and 13.5g of a-22 was used instead of amine a-2, whereby 17g of intermediate 31 was obtained (yield 70%, mass [ M + ] ═ 839).

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 17g of the intermediate 31 was used instead of the intermediate 2, whereby 3.2g of the compound 21 was obtained (yield 19%, mass [ M + ]: 813).

PREPARATION EXAMPLE 22 Synthesis of Compound 22

The preparation was carried out in the same manner as the preparation method of intermediate 1 of preparation example 1 except that 10g of 1-bromo-3-chloro-5-methylbenzene was used instead of 1-bromo-2,3-dichloro-5-methylbenzene and 22g of amine a-23 was used instead of amine a-1, whereby 21g of intermediate 32 was obtained (yield 74%, mass [ M + ] ═ 581).

Under a nitrogen atmosphere, 21g of intermediate 32, 4.4g of 2, 4-dimethylaniline, 5.2g of sodium tert-butoxide, 0.36g of bis (tri-tert-butylphosphine) palladium (0) (Pd (P (t-Bu)₃)₂) After addition to 300mL of toluene, the mixture was heated and stirred at 120 ℃ for 4 hours. After the amination reaction was completed, 6.9g of 1-bromo-3-chlorobenzene was immediately added dropwise, followed by stirring for 2 hoursThen (c) is performed. After the reaction is finished, cooling the reaction liquid to room temperature, adding water and NH₄Cl, after separation, MgSO₄(anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 17g of intermediate 33 (yield 61%, mass [ M + ]]＝776)。

17g of intermediate 33 were dissolved in dichlorobenzene under nitrogen atmosphere, and 14g of boron triiodide (BI) was added dropwise₃) After that, it was heated to 130 ℃ and stirred for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature, dissolved in toluene and extracted, and MgSO₄(anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 5.5g of intermediate 34 (yield 32%, mass [ M +)]＝784)。

The preparation was carried out in the same manner as in the preparation of intermediate 2 of preparation example 1 except that 5.5g of intermediate 34 was used instead of intermediate 1 and 1.2g of a-5 was used instead of amine a-2, whereby 17g of compound 22 was obtained (yield 81%, mass [ M + ]. 917).

PREPARATION EXAMPLE 23 Synthesis of Compound 23

Production was carried out in the same manner as the production method of intermediate 2 of production example 1 except that 15g of intermediate 8 was used instead of intermediate 1 and 13g of a-18 was used instead of amine a-2, whereby 20g of intermediate 35 was obtained (yield 75%, mass [ M + ] ═ 1061).

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 20g of the intermediate 35 was used instead of the intermediate 2, whereby 3.5g of the compound 23 was obtained (yield 18%, mass [ M + ] ═ 1035).

PREPARATION EXAMPLE 24 Synthesis of Compound 24

After 50.0g of 1.3-dibromo-2-chloro-5-iodobenzene (1,3-dibromo-2-chloro-5-iodobenzene) was dissolved in 1.2L of Tetrahydrofuran (THF) under a nitrogen atmosphere, the temperature was maintained at-10 ℃. Then, 70mL (2.0M tetrahydrofuran solution) of isopropyl magnesium chloride (isopropyl magnesium chloride) was slowly added dropwise, followed by stirring at 0 ℃ for 1 hour. 37.2g of triphenylchlorosilane are added at the same temperature. After the reaction solution was warmed to 0 ℃ and stirred for about 1 hour, it was further stirred at ordinary temperature for 12 hours. Then, after diluting with ethyl acetate, saturated NH was added₄Cl solution (Saturated aq₄Cl), the reaction was terminated, and the organic layer was extracted with MgSO₄(anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 36g of intermediate 36 (yield 54%, mass [ M + ]]＝529)。

The preparation was carried out in the same manner as the preparation of intermediate 3 of preparation example 2 except that 20g of intermediate 36 was used instead of 2-bromo-1,3-diiodo-5-methylbenzene and 21g of amine a-1 was used instead of amine a-2, whereby 25g of intermediate 37 was obtained (yield 71%, mass [ M + ] ═ 930).

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 25g of the intermediate 37 was used instead of the intermediate 2, whereby 4.6g of the compound 24 was obtained (yield 19%, mass [ M + ]: 904).

PREPARATION EXAMPLE 25 Synthesis of Compound 25

The preparation was carried out in the same manner as in the preparation of intermediate 3 of preparation example 2 except that 15g of 1, 3-dibromo-2-chlorobenzene was used instead of 2-bromo-1,3-diiodo-5-methylbenzene, whereby 28g of intermediate 38 was obtained (yield 75%, mass [ M + ] ═ 672).

The preparation was carried out in the same manner as the preparation of compound 1 of preparation example 1 except that 28g of intermediate 38 was used instead of intermediate 2, whereby 6.8g of intermediate 39 was obtained (yield 25%, mass [ M + ]: 645).

6.8g of intermediate 39 was dissolved in 100mL of chloroform under a nitrogen atmosphere, and 1.9g of N-bromosuccinimide was added thereto over 30 minutes, followed by stirring at room temperature for 4 hours. Adding distilled water to the reaction solution to terminate the reaction, extracting the organic layer with MgSO₄(anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by column chromatography (developing solution: hexane/ethyl acetate ═ 1:1 (volume ratio)), whereby 5.2g of intermediate 40 was obtained (yield 68%, mass [ M + ]]＝724)。

After 5.2g of intermediate 40 were dissolved in 60mL of tetrahydrofuran (anhydrous THF) under nitrogen, the temperature was reduced to-78 deg.C. Then, 5.7mL of n-butyllithium (n-BuLi (2.5M hexane solution)) was slowly added dropwise thereto, and the mixture was stirred for 1 hour. After completion of the lithium halide exchange reaction, 1.2mL of trimethylchlorosilane was dissolved in 5mL of tetrahydrofuran (anhydrous) and slowly added dropwise. After the reaction solution was stirred for about 1 hour while maintaining at-78 deg.C, the organic layer was extracted with dichloromethane, and MgSO was added₄(anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by column chromatography (developing solution: hexane/ethyl acetate ═ 1:1 (volume ratio)), whereby 3.5g of compound 25 was obtained (yield 68%, mass [ M + ]]＝747)。

PREPARATION EXAMPLE 26 Synthesis of Compound 26

22g of intermediate 41 (yield 75%, mass [ M + ]. 860) was obtained by the same production method as that of intermediate 2 of production example 1, except that 16g of a-24 was used instead of amine a-2.

The preparation was carried out in the same manner as the preparation method of compound 1 in preparation example 1 except that 14g of intermediate 41 was used instead of intermediate 2, whereby 4.2g of compound 26 was obtained (yield 20%, mass [ M + ]. 833).

PREPARATION EXAMPLE 27 Synthesis of Compound 27

The preparation was carried out in the same manner as in the preparation of intermediate 2 of preparation example 1 except that 12.6g of a-25 was used instead of amine a-2, whereby 20g of intermediate 42 was obtained (yield 76%, mass [ M + ]: 773).

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 20g of the intermediate 42 was used instead of the intermediate 2, whereby 4.1g of the compound 27 was obtained (yield 21%, mass [ M + ]: 746).

PREPARATION EXAMPLE 28 Synthesis of Compound 28

The preparation was carried out in the same manner as the preparation of intermediate 2 of preparation example 1 except that 15g of intermediate 21 was used instead of intermediate 1 and a-26 was used instead of amine a-2, whereby 17g of intermediate 43 was obtained (yield 67%, mass [ M + ]. 1106).

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 17g of the intermediate 43 was used instead of the intermediate 2, whereby 3.6g of the compound 28 was obtained (yield 22%, mass [ M + ]: 1079).

PREPARATION EXAMPLE 29 Synthesis of Compound 29

The preparation was carried out in the same manner as the preparation of intermediate 1 of preparation example 1 except that 12.8g of a-27 was used instead of a-1, whereby 16g of intermediate 44 was obtained (yield 70%, mass [ M + ]: 365).

Production was carried out in the same manner as the production method of intermediate 2 of production example 1 except that 16g of intermediate 44 was used instead of intermediate 1 and 22g of a-18 was used instead of amine a-2, whereby 26g of intermediate 45 was obtained (yield 71%, mass [ M + ]: 832).

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 17g of the intermediate 45 was used instead of the intermediate 2, whereby 4.1g of the compound 29 was obtained (yield 16%, mass [ M + ]: 805).

PREPARATION EXAMPLE 30 Synthesis of Compound 30

22g of intermediate 46 (yield 70%, mass [ M + ]. 926) was obtained by performing the production in the same manner as in the production method of intermediate 2 of production example 1, except that 17.8g of a-28 was used instead of amine a-2.

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 22g of the intermediate 46 was used instead of the intermediate 2, whereby 4.3g of the compound 30 was obtained (yield 20%, mass [ M + ]: 900).

PREPARATION EXAMPLE 31 Synthesis of Compound 31

20g of intermediate 7, 4.6g of 2-fluoroboric acid, 11.7g of potassium phosphate were added]220mL of 1, 4-bis

After an alkane and 50mL of water, 0.48g of tetrakis (triphenylphosphine) palladium (0) [ tetrapkis (triphenylphosphin) palladium (0) was added](Pd(PPh₃)₄) After that, the mixture was stirred with heating for 16 hours. After the reaction, the reaction mixture was cooled to room temperature, the organic solvent was removed, dissolved in toluene and extracted, and the organic solvent was extracted with MgSO₄(anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane), whereby 9.5g of intermediate 47 (yield 66%Mass [ M +]＝521)。

14g of intermediate 48 (yield 78%, mass [ M + ]: 982) was obtained by performing the production in the same manner as in the production method of intermediate 2 of production example 1, except that 9.1g of a-29 was used instead of amine a-2.

The preparation was carried out in the same manner as the preparation method of the compound 1 in the preparation example 1 except that 14g of the intermediate 48 was used instead of the intermediate 2, thereby obtaining 3.2g of the compound 31 (yield 23%, mass [ M + ]: 956).

PREPARATION EXAMPLE 32 Synthesis of Compound 32

Production was carried out in the same manner as the production method of intermediate 8 of production example 5 except that 4.6g of a-30 was used instead of amine a-5, whereby 12g of intermediate 49 was obtained (yield 73%, mass [ M + ]: 592).

The preparation was carried out in the same manner as the preparation method of intermediate 2 in preparation example 1 except that 12g of intermediate 49 was used instead of intermediate 1 and 7.0g of a-31 was used instead of amine a-2, whereby 13g of intermediate 50 was obtained (yield 71%, mass [ M + ]: 899).

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 13g of the intermediate 50 was used instead of the intermediate 2, thereby obtaining 2.9g of the compound 32 (yield 23%, mass [ M + ]: 873).

PREPARATION EXAMPLE 33 Synthesis of Compound 33

14g of intermediate 51 (yield 69%, mass [ M + ]: 739) was obtained by a method similar to the method for producing intermediate 8 of production example 5, except that 8.7g of a-31 was used instead of amine a-5.

The preparation was carried out in the same manner as the preparation of intermediate 2 of preparation example 1 except that 14g of intermediate 51 was used instead of intermediate 1, whereby 16g of intermediate 52 was obtained (yield 76%, mass [ M + ]: 1108).

The preparation was carried out in the same manner as the preparation method of the compound 1 in preparation example 1 except that 16g of the intermediate 52 was used instead of the intermediate 2, whereby 3.4g of the compound 33 was obtained (yield 22%, mass [ M + ]: 1081).

Production example 34: preparation of Compound E1

10g of spiro [ fluorene-9, 9' -thioxanthene]-1-ylboronic acid and 8.8g of the above-mentioned compound 2- ([1,1' -biphenyl)]After completely dissolving (4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine in tetrahydrofuran (200mL), 10.6g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 14g (yield 84%) of compound E1. MS [ M + H ]]⁺＝657。

Production example 35: preparation of Compound E2

10g of spiro [ fluorene-9, 9' -xanthene]After completely dissolving (2-phenylboronic acid) and 9.8g of the above-mentioned compound 2-chloro-4, 6-di (naphthalen-1-yl) -1,3, 5-triazine in tetrahydrofuran (200mL), 11.1g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 15g (yield 85%) of compound E2. MS [ M + H ]]⁺＝665。

Production example 36: preparation of Compound E3

10g of spiro [ fluorene-9, 9' -xanthene]After-2-ylboronic acid and 8.5g of the above-mentioned compound 4- (4-chlorophenyl) -2-phenylquinazoline were completely dissolved in tetrahydrofuran (200mL), 11.1g of potassium carbonate was added dissolved in 60mL of water. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 14g (yield 86%) of compound E3. MS [ M + H ]]⁺＝614

Production example 37: preparation of Compound E4

10g of spiro [ fluorene-9, 9' -thioxanthene]After completely dissolving (i) 3-phenylboronic acid and 8.5g of the above compound, 4- (4-chlorophenyl) -2, 6-diphenylpyrimidine in tetrahydrofuran (200mL), 10.6g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 13g (yield 78%) of compound E4. MS [ M + H ]]⁺＝656

Production example 38: preparation of Compound E5

10g of spiro [ fluorene-9, 9' -thioxanthene]After (4-yl) boronic acid and 6.8g of the above-mentioned compound 2-chloro-4, 6-diphenyl-1, 3, 5-triazine were completely dissolved in tetrahydrofuran (200mL), 10.6g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. Will be at temperatureCooling to normal temperature, and after the reaction is finished, removing the potassium carbonate solution and filtering a white solid. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 11g (yield 77%) of compound E5. MS [ M + H ]]⁺＝565

Production example 39: preparation of Compound E6

10g of spiro [ dibenzo [ c, h ]]Xanthene-7, 9' -fluorene]After (i) -2' -ylboronic acid and 5.6g of the above compound, 2-chloro-4, 6-diphenyl-1, 3, 5-triazine were completely dissolved in tetrahydrofuran (200mL), 8.7g of potassium carbonate was dissolved in 60mL of water and added. After 0.8g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 11g (yield 79%) of compound E6. MS [ M + H ]]⁺＝665

Production example 40: preparation of Compound E7

10g of spiro [ fluorene-9, 9' -xanthene]After (i) -2-ylboronic acid and 11.5g of the above compound, 9- (4- (6-chloro-2-phenylpyrimidin-4-yl) phenyl) -9H-carbazole were completely dissolved in tetrahydrofuran (200mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 14g (yield 72%) of compound E7. MS [ M + H ]]⁺＝729。

Production example 41: preparation of Compound E8

10g of spiro [ fluorene-9, 9' -xanthene]-2-ylboronic acid and 11.2g of the above compound 2-chloro-4-phenyl-6- (4'- (pyridin-4-yl) - [1,1' -biphenyl]After completely dissolving (E) -3-yl) -1,3, 5-triazine in tetrahydrofuran (200mL), 11g of potassium carbonate was added dissolved in 60mL of water. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 14g (yield 73%) of compound E8. MS [ M + H ]]⁺＝718

Production example 42: preparation of Compound E9

10g of (3'- (2, 6-diphenylpyrimidin-4-yl) spiro [ fluorene-9, 9' -xanthene)]-2-yl) boronic acid and 4.4g of the above compound 4-chloro-2, 6-diphenylpyrimidine were completely dissolved in tetrahydrofuran (200mL), and then 6.9g of potassium carbonate was added dissolved in 60mL of water. After 0.6g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 10g (yield 76%) of compound E9. MS [ M + H ]]⁺＝794。

Production example 43: preparation of Compound E10

10g of spiro [ fluorene-9, 9' -xanthene]After completely dissolving (11.5 g) of the 2' -ylboronic acid and (4-chloro-2, 6-diphenylpyrimidine) above in tetrahydrofuran (200mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. Will have passedThe filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 16g (yield 82%) of compound E10. MS [ M + H ]]⁺＝731。

Production example 44: preparation of Compound E11

10g of spiro [ fluorene-9, 9' -xanthene]After (i) -3' -ylboronic acid and 11.7g of the above-mentioned compound 2- (2-bromonaphthalen-1-yl) -4, 6-diphenyl-1, 3, 5-triazine were completely dissolved in tetrahydrofuran (200mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 15g (yield 82%) of compound E11. MS [ M + H ]]⁺＝691。

Production example 45: preparation of Compound E12

10g of spiro [ fluorene-9, 9' -xanthene]After (i) -3' -ylboronic acid and 9.2g of the above-mentioned compound 2- (6-chloropyridin-3-yl) -4, 6-diphenyl-1, 3, 5-triazine were completely dissolved in tetrahydrofuran (200mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 13g (yield 76%) of compound E12. MS [ M + H ]]⁺＝642。

Production example 46: preparation of Compound E13

10g of spiro [ fluorene ]-9,9' -thioxanthene]After completely dissolving (i) -3' -ylboronic acid and 10.1g of the above-mentioned 2- (5-bromothien-2-yl) -4, 6-diphenyl-1, 3, 5-triazine in tetrahydrofuran (200mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 13g (yield 77%) of compound E13. MS [ M + H ]]⁺＝663。

Production example 47: preparation of Compound E14

10g of spiro [ fluorene-9, 9' -thioxanthene]After completely dissolving (11.9 g) of the above-mentioned (4- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) phenyl) -10H-phenothiazine and (4' -phenylboronic acid) in tetrahydrofuran (200mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 16g (yield 81%) of compound E14. MS [ M + H ]]⁺＝778。

Production example 48: preparation of Compound E15

10g of spiro [ fluorene-9, 9' -thioxanthene]-4' -ylboronic acid and 9.4g of the above-mentioned 4' - (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) - [1,1' -biphenylyl ] acid]After completely dissolving the 2-carbonitrile in tetrahydrofuran (200mL), 11g of potassium carbonate was added dissolved in 60mL of water. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate to thereby yield 14g (yield 81%)Compound E15. MS [ M + H ]]⁺＝682。

Production example 49: preparation of Compound E16

10g of (13, 13-dimethyl-13H-indeno [1, 2-l)]Phenanthrene 11-yl) boronic acid and 10.2g of the above-mentioned 2- ([1,1' -biphenyl]After completely dissolving (2-yl) -4-chloro-6-phenyl-1, 3, 5-triazine in tetrahydrofuran (200mL), 11g of potassium carbonate was added dissolved in 60mL of water. After 1.0g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 14g (yield 79%) of compound E16. MS [ M + H ]]⁺＝603。

Production example 50: preparation of Compound E17

10g of (9, 9-diphenyl-9H-fluoren-4-yl) boronic acid and 11.5g of the abovementioned 2- ([1,1':3', 1' -terphenyl) are reacted]After completely dissolving (5' -yl) -4-chloro-6-phenyl-1, 3, 5-triazine in tetrahydrofuran (200mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After 1.0g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 15g (yield 77%) of compound E17. MS [ M + H ]]⁺＝703。

Production example 51: preparation of Compound E18

10g of (9, 9-dimethyl-7-phenyl-9H-fluoren-4-yl) boronic acid and 12.5g of 2- ([1,1' -biphenyl]After completely dissolving (4-yl) -4-chloro-6- (naphthalen-1-yl) -1,3, 5-triazine in tetrahydrofuran (200mL), 13.2g of potassium carbonate was added dissolved in 60mL of water. After 1.1g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 16g (yield 80%) of compound E18. MS [ M + H ]]⁺＝629。

Production example 52: preparation of Compound E19

10g of (9, 9-diphenyl-9H-fluoren-2-yl) boronic acid and 12.3g of 2- ([1,1' -biphenyl]After completely dissolving (E) -3-yl-4-chloro-6- (phenanthren-9-yl) -1,3, 5-triazine in tetrahydrofuran (200mL), 13.2g of potassium carbonate was added dissolved in 60mL of water. After 1.0g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 15g (yield 75%) of compound E19. MS [ M + H ]]⁺＝727。

Production example 53: preparation of Compound E20

10g of (9, 9-diphenyl-9H-fluoren-1-yl) boronic acid and 10.6g of 2- ([1,1' -biphenyl]After completely dissolving (E) -2-yl-4-chloro-6- (naphthalen-2-yl) -1,3, 5-triazine in tetrahydrofuran (200mL), 11.1g of potassium carbonate was added dissolved in 60mL of water. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, thereby producing 14g (yield 79%) of compound E20. MS [ M + H ]]⁺＝677。

All of the heterocyclic compounds of the

above chemical formulae

1 and 2 described in the present specification can be produced by appropriately combining the production formulae described in the examples of the present specification and the above intermediates based on general technical common knowledge.

< device example 1>

Example 1

ITO (indium tin oxide) is added

The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode thus prepared, the above HI-A compound is added

The hole injection layer is formed by thermal vacuum deposition. Sequentially adding the HAT compound to the hole injection layer

And HT-A compounds as described above

Vacuum evaporation is performed to form a hole transport layer. On the hole transport layer, the following HT-B and

the electron blocking layer is formed by vacuum evaporation.

Then, on the hole transport layer, the film thickness

The light-emitting layer was formed by vacuum vapor deposition of a BH-1 Compound and Compound 1(Compound 1) at a weight ratio of 100: 2.

On the light-emitting layer, compound E1 was vacuum-deposited to form a layer

Forming a hole blocking layer. On the hole-blocking layer, compound ET and the following LiQ compound were vacuum-evaporated at a weight ratio of 1:1 to obtain a positive hole-blocking layer

The thickness of (a) forms an electron injection and transport layer. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to

Thickness of aluminum and

is deposited to form a cathode.

In the above process, the evaporation rate of the organic material is maintained at 0.4-0.4

Lithium fluoride maintenance of cathode

Deposition rate of (3), aluminum maintenance

The vapor deposition rate of (2), the degree of vacuum of which is maintained at 1X 10 during vapor deposition^-7To 5X 10^-5And thus an organic light emitting device was manufactured.

Examples 2 to 18 and comparative examples 1 to 8

An organic light-emitting device was produced in the same manner as in example 1, except that the dopant material and the hole-blocking layer material of the light-emitting layer were the materials described in table 1 below.

For the organic light emitting devices of examples 1 to 18 and comparative examples 1 to 8 described above, at 10mA/cm²The driving voltage and the luminous efficiency (conversion efficiency) were measured at a current density of 15mA/cm²Was measured at a current density of (1) and the time at which 95% of the initial luminance was obtained was marked (T95). The results are shown in table 1 below.

[ Table 1]

In the above table, as the dopant and the hole blocking layer material of the light emitting layer, all of comparative examples 1 to 3 used compounds different from the compounds of

chemical formulae

1 and 2 of the present invention. Examples 1 to 14 showed low voltage and high efficiency characteristics as compared with comparative examples 1 to 3, and in particular, it was confirmed that the lifetime was greatly increased.

Comparative examples 4 to 8 used the compound of the present invention as either a dopant of the light-emitting layer or a hole-blocking layer material. When example 1 and comparative example 4, example 4 and comparative example 5, and example 12 and comparative example 6 are compared with each other, it is understood that the same substance is used as a dopant substance for a light-emitting layer, but the substance used for a hole-blocking layer is different, and thus the difference in effect is exhibited when the same substance is applied to a device. Examples 1,4 and 12 were confirmed to have low voltage, high efficiency and long life characteristics as compared with comparative examples 4,5 and 6.

Example 2 and comparative example 7, examples 9, 18 and comparative example 8 are each device materials using the same hole blocking substance, using different dopant substances. Examples 2, 9 and 18 can be confirmed to have low voltage, high efficiency and long life characteristics compared to comparative examples 7 and 8 due to the difference in dopant species.

< device example 2>

Example 19

ITO (indium tin oxide) is added

The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, a product of Hill corporation was used as the detergent, and distilled water obtained by twice filtration using a filter manufactured by Millipore corporation was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode thus prepared, the following HI-A compound was added

The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, HAT compound described below is sequentially added

And the following HT-A compounds

Vacuum evaporation is performed to form a hole transport layer.

Then, on the hole transport layer, the film thickness

The BH-2 compound and the following compound 2 are mixed in a weight ratio of 100:2Vacuum evaporation is performed to form a light emitting layer.

On the light-emitting layer, the compound E10 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 to form a layer

Thickness of aluminum and

is deposited to form a cathode.

Lithium fluoride maintenance of cathode

Deposition rate of (3), aluminum maintenance

Examples 20 to 28 and comparative examples 9 to 16

An organic light-emitting device was produced in the same manner as in example 19, except that the dopant material and the electron injection and transport layer material of the light-emitting layer were the same as those shown in table 2 below.

For the organic light emitting devices of the above examples 19 to 28 and comparative examples 9 to 16, at 10mA/cm²The driving voltage and the luminous efficiency (conversion efficiency) were measured at a current density of 15mA/cm²Was measured at a current density of (1) and the time at which 95% of the initial luminance was obtained was marked (T95). The results are shown in table 2 below.

[ Table 2]

In table 2 above, as the dopant and the hole blocking layer material of the light emitting layer, comparative examples 9 to 11 all used compounds different from the compounds of

chemical formulae

1 and 2 of the present invention.

Examples 19 to 28 can confirm that they exhibit low voltage, high efficiency and long life characteristics as compared with comparative examples 9 to 11.

Comparative examples 12 to 14 used the same dopant species as in examples 19, 20 and 24, respectively, except that different species were used in the electron injecting and transporting layers. Examples 19, 20 and 24 showed low voltage, high efficiency and long life characteristics as compared with comparative examples 12 to 14.

Comparative examples 15 and 16 used the same electron injection and transport layer materials as in examples 24, 26 and 23, 28, respectively. However, examples 24, 26 and 23, 38, which are different in dopant substance, can confirm that more excellent effects are exhibited when applied to devices, as compared to comparative examples 15 and 16, respectively.

< device example 3>

Example 29

ITO (indium tin oxide) is added

The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent was a product of Hill corporation, and the distilled water was filtered using a filter manufactured by Millipore corporationTwice distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.

And HT-A compounds as described above

the electron blocking layer is formed by vacuum evaporation.

Then, on the hole transport layer, the film thickness

The light-emitting layer was formed by vacuum vapor deposition of a BH-3 compound and compound 5 at a weight ratio of 100: 2.

On the light-emitting layer, compound E10 was vacuum-deposited to form a layer

Forming a hole blocking layer. On the hole-blocking layer, compound E2 and the following LiQ compound were vacuum-evaporated at a weight ratio of 1:1 to obtain a positive hole-blocking layer

Thickness of aluminum and

is deposited to form a cathode.

Lithium fluoride maintenance of cathode

Deposition rate of (3), aluminum maintenance

Examples 30 to 34 and comparative examples 17 to 19

An organic light-emitting device was produced in the same manner as in example 29, except that the dopant substance, the hole-blocking layer substance, and the electron injection and transport layer substance of the light-emitting layer were each as described in table 3 below.

For the organic light emitting devices of the above examples 29 to 34 and comparative examples 17 to 19, at 10mA/cm²The driving voltage and the luminous efficiency (conversion efficiency) were measured at a current density of 15mA/cm²Was measured at a current density of (1) and the time at which 95% of the initial luminance was obtained was marked (T95). The results are shown in table 3 below.

[ Table 3]

In table 3 above, comparative example 17 is data in which compounds not of the chemical formula of the present invention were all used as a dopant substance, a hole blocking layer substance, an electron injecting and transporting layer substance. Comparative example 18 used the same hole blocking layer material as in example 29, differing only in the dopant material and the electron injecting and transporting layer material.

Comparative example 19 used the same electron injecting and transporting layer species as in example 34, with different species used in the dopant and hole blocking layer. Therefore, examples 29 and 34 can confirm the excellent effects of low voltage, high efficiency, and long life as compared with comparative examples 18 and 19.

Claims

1. An organic light emitting device comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode,

wherein the organic layer comprises: a first organic layer including a compound represented by the following chemical formula 1 and a second organic layer including a compound represented by the following chemical formula 2:

chemical formula 1

In the chemical formula 1, the first and second organic solvents,

chemical formula 3

In the chemical formula 3, the first and second organic solvents,

the dotted line is the site of attachment to A1, A2, A3, B1 or B2,

x is C or Si, and X is C or Si,

n1 and n5 are each an integer of 0 to 4,

n2 and n4 are each an integer of 0 to 5,

n3 is an integer from 0 to 3,

n1+ n2+ n3+ n4+ n5 is 1 or more,

chemical formula 2

In the chemical formula 2,

a31 is an integer from 0 to 8,

a31 is plural, R3-1 may be the same or different from each other,

chemical formula 4

In the chemical formula 4, the first and second organic solvents,

the dotted line is the site of attachment to the nucleus,

X₁to X₃Are identical to or different from each other and are each independently N or CR,

X₁to X₃At least one of which is N,

r is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group,

L₁to L₃The same or different from each other, each independently is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.

2. The organic light emitting device according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1:

chemical formula 1-1

In the chemical formula 1-1, R1 to R5 and n1 to n5 are the same as defined in the chemical formula 1.

3. The organic light-emitting device according to claim 1, wherein R1, R2, R4 and R5, which are the same or different from each other, are each independently hydrogen; deuterium; a halogen group; a cyano group; an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 30 carbon atoms which is substituted or unsubstituted with deuterium; an arylamine group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group and an alkyl group having 1 to 10 carbon atoms or a substituent in which 2 or more groups selected from the group are bonded; a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium, or represented by the chemical formula 3,

r3 is hydrogen; deuterium; a halogen group; a cyano group; an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 30 carbon atoms which is substituted or unsubstituted with deuterium; an arylamine group having 6 to 60 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a silyl group, or a substituent in which 2 or more groups selected from the group are bonded; an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium, a halogen group, or a cyano group; a heterocyclic group of 2 to 30 carbon atoms substituted or unsubstituted with deuterium, or represented by the chemical formula 3.

4. The organic light emitting device according to claim 1, wherein the chemical formula 2 is represented by the following chemical formula 2-1:

chemical formula 2-1

In the chemical formula 2-1,

y is CR111R112, O or S,

a32 is an integer from 0 to 8,

b33 is an integer from 0 to 8,

n33 is 0 or 1 and,

when n33 is 0, hydrogen is bonded to each of the 2 benzene rings bonded to Y,

chemical formula 4

The dotted line is the site of attachment to the nucleus,

Ar₁and Ar₂The same or different from each other, each independently is a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

X₁to X₃At least one of which is N,

r are the same or different from each other and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group,

L₁to L₃Are the same or different from each other, eachIndependently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.

5. An organic light-emitting device according to claim 4 wherein Y is O or S.

6. The organic light emitting device according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:

7. the organic light emitting device according to claim 1, wherein the chemical formula 2 is any one of the following compounds:

8. the organic light emitting device according to claim 1, wherein the chemical formula 2 is any one of compounds described in the following table:

9. the organic light emitting device according to claim 1, wherein the first electrode is an anode, the second electrode is a cathode, the first organic layer is a light emitting layer, and the second organic layer is provided between the second electrode and the first organic layer.

10. The organic light emitting device according to claim 1, wherein the organic layer comprises 2 or more light emitting layers, and 1 layer of the 2 or more light emitting layers contains the compound represented by chemical formula 1.

11. The organic light-emitting device according to claim 1, wherein the second organic layer further comprises 1 or 2 or more n-type dopants selected from alkali metals and alkaline earth metals.

12. The organic light emitting device according to claim 1, wherein the second organic layer comprises 1 or more layers selected from a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.