CN116917299A

CN116917299A - Polycyclic compound and organic light emitting device including the same

Info

Publication number: CN116917299A
Application number: CN202280018904.XA
Authority: CN
Inventors: 琴水井; 金京嬉; 曹惠慜; 金明坤; 金恩镐; 金弘文; 李禹哲
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2022-01-13
Filing date: 2022-12-06
Publication date: 2023-10-20
Also published as: KR20230109546A; WO2023136476A1

Abstract

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

Description

Polycyclic compound and organic light emitting device including the same

Technical Field

The present application claims priority from korean patent application No. 10-2022-0005316 filed to the korean patent office on day 1 and 13 of 2022, the entire contents of which are incorporated herein.

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 and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, 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. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition to the ground state again.

There is a continuing need to develop new materials for use in organic light emitting devices as described above.

Disclosure of Invention

Technical problem

In the present specification, polycyclic compounds and organic light emitting devices including the same are described.

Solution to the problem

The present specification provides polycyclic compounds of the following chemical formula 1.

[ chemical formula 1]

In the above-mentioned chemical formula 1,

cy1 is one selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring, and a substituted or unsubstituted aliphatic heterocyclic ring, or a ring formed by fusing 2 or more rings selected from the above group,

x1 is C or N, and the total number of the components is equal to or less than zero,

x2 and X3 are identical to or different from each other and are each, independently of one another, C, N, O or S,

at least one of X1 to X3 is N, or X1 is C, at least one of X2 and X3 is N, O or S,

z is O, S, NR, CR12R13 or SiR12R13,

r1 to R4 and R11 to R13 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted ring,

r1 is an integer of 0 to 4, r2 and r3 are each an integer of 0 to 3, r4 is an integer of 0 to 2,

when r1 to r3 are each 2 or more, the substituents in brackets are the same or different from each other,

when r4 is 2, the substituents in brackets are the same or different from each other.

In addition, the present specification provides an organic light emitting device, including: a first electrode, a second electrode disposed opposite to the first electrode, and 1 or more organic layers disposed between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the polycyclic compound.

Effects of the invention

The compound of the present invention can be used as a material of an organic layer of an organic light emitting device. When the compound of the present invention is contained in the light-emitting layer of an organic light-emitting device, an organic light-emitting device having high color reproducibility can be produced.

Drawings

Fig. 1 and 2 illustrate examples of an organic light emitting device according to the present invention.

< description of symbols >

1: substrate board

2: anode

3: light-emitting layer

4: cathode electrode

5: first hole injection layer

6: a second hole injection layer

7: hole transport layer

8: electron blocking layer

9: a first electron transport layer

10: a second electron transport layer

11: electron injection layer

Detailed Description

The present specification will be described in more detail below.

The organic light-emitting device to which the conventional boron compound is applied has a disadvantage of short lifetime. However, the compound represented by chemical formula 1 contains a heteroatom, so that the first triplet excitation energy of chemical formula 1 decreases, and the difference between the first singlet excitation energy and the first triplet excitation energy increases. Accordingly, the compound represented by chemical formula 1 suppresses triplet quenching (Triplet quenching), and the device lifetime of an organic light emitting device including the same is increased under a host-dopant system.

In the present specification, when a certain component is referred to as "including" or "comprising" a certain component, unless otherwise specified, it means that other components may be further included, and not excluded.

In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is connected to the other member but also the case where another member exists between the two members.

In the present specification, a dotted line is a position where it is connected or condensed with other parts.

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

The term "substituted" as used herein means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same 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, halogen group, cyano (-CN), alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, condensed ring group of aromatic hydrocarbon ring and aliphatic hydrocarbon ring, and heterocyclic group, or with a substituent in which 2 or more substituents of the above exemplified substituents are linked, or without any substituent. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.

In one embodiment of the present specification, "substituted or unsubstituted" means substituted with 1 or more substituents selected from the group consisting of deuterium, halogen groups, cyano (-CN), C1-C20 alkyl, C3-C60 cycloalkyl, C1-C20 alkylsilyl, C6-C90 arylsilyl, C1-C20 alkylamino, C6-C90 arylamine, C6-C60 aryl, fused ring groups of C9-C60 aromatic and aliphatic hydrocarbon rings, and heterocyclic groups of C2-C60, or with substituents joined by 2 or more groups selected from the above groups, or does not have any substituent.

In one embodiment of the present specification, "substituted or unsubstituted" means substituted with 1 or more substituents selected from the group consisting of deuterium, halogen groups, cyano (-CN), C1-C10 alkyl, C3-C30 cycloalkyl, C1-C10 alkylsilyl, C6-C60 arylsilyl, C1-C10 alkylamino, C6-C60 arylamine, C6-C30 aryl, fused ring groups of C9-C30 aromatic and aliphatic hydrocarbon rings, and heterocyclic groups of C2-C30, or with substituents bonded with 2 or more groups selected from the above groups, or does not have any substituent.

In one embodiment of the present specification, "substituted or unsubstituted" means substituted with 1 or more substituents selected from the group consisting of deuterium, halogen groups, cyano (-CN), C1-C6 alkyl, C3-C20 cycloalkyl, C1-C10 alkylsilyl, C6-C40 arylsilyl, C1-C10 alkylamino, C6-C40 arylamine, C6-C20 aryl, fused ring groups of C9-C20 aromatic and aliphatic hydrocarbon rings, and heterocyclic groups of C2-C20, or with substituents joined by 2 or more groups selected from the above groups, or does not have any substituent.

In the present specification, the connection of 2 or more substituents means that hydrogen of any one substituent is replaced with other substituents. For example, isopropyl group may be linked to phenyl group to formSuch substituents.

In this specification, 3 substituent linkages include not only (substituent 1) to (substituent 2) to (substituent 3) linked in succession, but also (substituent 2) and (substituent 3) linked in (substituent 1). For example, 2 phenyl groups and isopropyl groups may be linked to formSuch substituents. The same description applies to the case where 4 or more substituents are linked.

In the present specification, "substituted with A1 or A2" includes not only the case of substitution with A1 alone or substitution with A2 alone, but also the case of substitution with A1 and A2.

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

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

In the present specification, the nailThe silane groups may be selected from the group consisting of-SiY ₁₁ Y ₁₂ Y ₁₃ The chemical formula of (A) is shown in the specification, Y is shown in the specification ₁₁ 、Y ₁₂ And Y ₁₃ Each may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group is specifically, but not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.

In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the above alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. According to another embodiment, the above alkyl group has 1 to 4 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, and the like.

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

In the present specification, the amine group may be selected from the group consisting of-NH ₂ The alkyl amine group, alkyl aryl amine group, aryl heteroaryl amine group, alkyl heteroaryl amine group and heteroaryl amine group are not particularly limited, but are preferably 1 to 60 carbon atoms. For arylamine groups, the number of carbon atoms is from 6 to 60. According to another embodiment, the arylamine group has a number of carbon atoms from 6 to 40. Specific examples of the amine group include methylamino group, dimethylamino group, ethylamino group, diethylamino group, phenylamine group, naphthylamino group, biphenylamino group, anthracenylamino group, 9-methylanthracenylamino group, diphenylamino group, N-phenylnaphthylamino group, xylylamino group, N-phenyltolylamino group, triphenylamino group, N-phenylbiphenylamino group, N-phenylnaphthylamino group, N-biphenylnaphthylamino group, N-naphthylfluorenylamino groupExamples of the amine group include, but are not limited to, a group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrylamino group, an N-phenylfluorenylamino group, an N- (4- (tert-butyl) phenyl) -N-phenylamino group, an N, N-bis (4- (tert-butyl) phenyl) amino group, and an N, N-bis (3- (tert-butyl) phenyl) amino group.

In the present specification, an alkylamino group means an amino group having an alkyl group substituted on N of the amino group, and includes a dialkylamino group, an alkylaryl amino group, and an alkylheteroaryl amino group.

In the present specification, arylamino group means an amino group having an aryl group substituted on N of the amino group, and includes diarylamino group, arylheteroarylamino group, and alkylaryl amino group.

In the present specification, a heteroarylamino group means an amino group substituted with a heteroaryl group on the N of the amino group, and includes a diheteroarylamino group, an arylheteroarylamino group, and an alkylheteroarylamino group.

In the present specification, alkylaryl amine group means an amine group having an alkyl group and an aryl group substituted on N of the amine group.

In the present specification, an arylheteroarylamino group means an amino group substituted with an aryl group and a heteroaryl group on N of the amino group.

In the present specification, an alkylheteroaryl amine group means an amine group substituted with an alkyl group and a heteroaryl group on the N of the amine group.

In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Cycloalkyl includes not only monocyclic groups, but also bicyclic groups such as bridgehead, fused ring, spiro ring (spiro) and the like. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, and the like, but not limited thereto.

In the present specification, a cycloolefin (cyclilkene) is a cyclic group having a double bond in a hydrocarbon ring, but not an aromatic group, and the number of carbon atoms is not particularly limited, but may be 3 to 60, and according to an embodiment, may be 3 to 30. Cycloolefins include not only monocyclic groups but also bicyclic groups such as bridgehead, fused rings, spiro rings and the like. Examples of the cycloolefin include, but are not limited to, cyclopropene, cyclobutene, cyclopentene, cyclohexene, and the like.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, triphenyl,A group, a fluorenyl group, etc., but is not limited thereto.

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 condensed on the aryl group. For example, tetrahydronaphthyl, indanyl, and dihydroanthracenyl of the structures below are included in substituted aryl groups. In the following structure, one of the carbon atoms of the benzene ring may be attached to other positions.

In the present specification, an aromatic hydrocarbon ring means a planar hydrocarbon ring in which pi electrons are completely conjugated, and the above description of aryl groups can be applied in addition to 2. The number of carbon atoms of the aromatic hydrocarbon ring may be 6 to 60, 6 to 30, 6 to 20, or 6 to 10.

In the present specification, the aliphatic hydrocarbon ring means a ring which is not aromatic and has a structure bonded in a cyclic manner. Examples of the aliphatic hydrocarbon ring include cycloalkyl and cycloalkenyl, and the above description of cycloalkyl and cycloalkenyl can be applied in addition to 2-valent alkyl. The aliphatic hydrocarbon ring may have a carbon number of 3 to 60, 3 to 30, 3 to 20, 3 to 10, 5 to 50, 5 to 30, 5 to 20, 5 to 10, or 5 to 6. The substituted aliphatic hydrocarbon ring includes an aliphatic hydrocarbon ring having an aromatic ring condensed therein.

In the present specification, the condensed ring of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring means a condensed ring of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring, and the condensed ring group of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring means a 1-valent group. Examples of the condensed ring group of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring include tetrahydronaphthyl, indanyl, and dihydroanthracenyl, but are not limited thereto.

In the present specification, when a substituent of an aromatic hydrocarbon ring or an aryl group is bonded to an adjacent substituent to form an aliphatic hydrocarbon ring, the aliphatic hydrocarbon ring contains 2 pi electrons (carbon-carbon double bonds) of the aromatic hydrocarbon ring or the aryl group even if there is no explicit double bond.

In the present specification, alkylaryl means aryl substituted with alkyl, and substituents other than alkyl may be further attached.

In the present specification, arylalkyl means an alkyl group substituted with an aryl group, and a substituent other than the aryl group may be further bonded.

In the present specification, an aryloxy group is an aryl group which is connected to an oxygen atom, and the above description about an aryl group can be applied to an aryl group. The aryl group of the aryloxy group is the same as exemplified above for the aryl group. Specifically, examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3, 5-dimethyl-phenoxy group, a 2,4, 6-trimethylphenoxy group, a p-t-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthracenyloxy group, a 2-anthracenyloxy group, a 9-anthracenyloxy group, a 1-phenanthrenyloxy group, a 3-phenanthrenyloxy group, a 9-phenanthrenyloxy group and the like, and as an arylthio group With phenylthio->2-Methylphenylthio4-tert-butylphenylthio-> And the like, but is not limited thereto.

In the present specification, the heterocyclic group is a ring group containing 1 or more heteroatoms in N, O, P, S, si and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to one embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include pyridyl, quinolyl, thienyl, dibenzothienyl, furyl, dibenzofuryl, naphthobenzofuryl, carbazolyl, benzocarbazolyl, naphthobenzothienyl, dibenzosilol (dibenzosilole), naphthobenzoxazolyl (naphthobenzoxazolilole), hexahydrocarbazolyl, dihydroacridinyl, dihydrodibenzosilacyclohexane, and phenoneOxazinyl (phenoxazine), phenothiazinyl (phenothiazine), dihydrodibenzosilacyclohexane, spiro (dibenzosilole-dibenzosilacyclohexane) group, spiro (acridine-fluorene) group, and the like, but are not limited thereto.

In this specification, the heteroaryl group is not aromatic, and the above description about the heterocyclic group can be applied.

In this specification, an "adjacent" group refers to a substituent substituted on an atom directly bonded to an atom substituted with the substituent, a substituent closest to the substituent in steric structure, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted in the benzene ring at the ortho (ortho) position and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other. In addition, substituents attached to consecutive 2 carbons in the aliphatic ring (4 in total) can also be interpreted as "adjacent" groups.

In the present specification, the meaning of "adjacent groups are bonded to each other to form a ring" in a substituent means that they are bonded to each other to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

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

In this specification, arylene groups other than the 2-valent groups may be used as described above with respect to aryl groups.

[ chemical formula 1]

In the above-mentioned chemical formula 1,

x1 to X3 are identical to or different from each other and are each, independently of one another, C, N, O or S,

at least one of X1 to X3 is N, O or S,

z is O, S, NR, CR12R13 or SiR12R13,

In one embodiment of the present description, X1 is C or N, X2 and X3 are the same or different from each other, each is independently C, N, O or S, at least one of X1 to X3 is N, or at least one of X2 and X3 is N, O or S when X1 is C.

In one embodiment of the present description, one or two of X1 to X3 is N.

In one embodiment of the present disclosure, X1 is C, X2 is NR4, O or S, and X3 is CR4.

In one embodiment of the present disclosure, X1 is C, X2 is CR4, and X3 is NR4, O, or S.

In one embodiment of the present disclosure, X1 and X3 are N and X2 is CR4.

In one embodiment of the present description, X1 and X3 are N and X2 is O or S.

In one embodiment of the present description, X1 to X3 are N.

In one embodiment of the present specification, chemical formula 1 is any one of the following chemical formulas 101 to 103.

[ chemical formula 101]

[ chemical formula 102]

[ chemical formula 103]

In the above-mentioned chemical formulas 101 to 103,

x4 is NR4, O or S,

x5 and X6 are identical to or different from each other and are each independently CR4 or N,

cy1, Z, R1 to R4 and R1 to R3 are as defined in chemical formula 1 above.

In one embodiment of the present disclosure, X5 is CR4 or N.

In one embodiment of the present disclosure, X6 is N.

In one embodiment of the present specification, cy1 is one selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring, and a substituted or unsubstituted aliphatic heterocyclic ring, or a ring selected from the group consisting of 2 or more rings in the above group being condensed.

In one embodiment of the present specification, cy1 is one selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring of C5 to C30, a substituted or unsubstituted aliphatic hydrocarbon ring of C3 to C30, a substituted or unsubstituted aromatic heterocyclic ring of C2 to C30, and a substituted or unsubstituted aliphatic heterocyclic ring of C2 to C30, or a ring of C2 to C60 formed by fusing 2 or more rings selected from the above groups.

In one embodiment of the present specification, cy1 is one selected from the group consisting of a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring, a substituted or unsubstituted C5-C20 aliphatic hydrocarbon ring, a substituted or unsubstituted C2-C20 aromatic heterocyclic ring, and a substituted or unsubstituted C2-C20 aliphatic heterocyclic ring, or a C2-C40 ring formed by fusing 2 or more rings selected from the above groups.

In one embodiment of the present specification, cy1 is one selected from the group consisting of a benzene ring, a cyclopentene ring, a cyclohexene ring, a furan ring, a thiophene ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, and an indole ring, or a ring in which 2 or more rings selected from the above groups are condensed.

In one embodiment of the present specification, cy1 is a benzene ring, a benzofuran ring, a dibenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, or a fluorene ring, and a cyclopentene ring or a cyclohexene ring may be further condensed on the Cy 1.

In one embodiment of the present specification, cy1 is a benzofuran ring, benzothiophene ring, or indole ring, and a cyclopentene ring or cyclohexene ring may be further fused to Cy 1.

In one embodiment of the present specification, cy1 is a substituted or unsubstituted benzene ring, a substituted or unsubstituted tetrahydronaphthalene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted dibenzothiophene ring, or a substituted or unsubstituted fluorene ring.

In one embodiment of the present specification, cy1 is a benzene ring, tetrahydronaphthalene ring, benzofuran ring, dibenzofuran ring, benzothiophene, dibenzothiophene, or fluorene ring.

In an embodiment of the present specification, R1 to R4 are the same or different from each other, each is independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or is combined with each other with an adjacent group to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R1 to R4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C1-C60 alkylsilyl, substituted or unsubstituted C6-C60 arylsilyl, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C9-C30 aromatic hydrocarbon ring and aliphatic hydrocarbon ring fused ring group, or substituted or unsubstituted C2-60 heterocyclic group, or are combined with each other to form a substituted or unsubstituted C5-C60 ring.

In one embodiment of the present specification, R1 to R4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C9-C30 aromatic hydrocarbon ring and aliphatic hydrocarbon ring fused ring group, or substituted or unsubstituted C2-C30 heterocyclic group, or form a substituted or unsubstituted C5-C30 ring with each other by combining adjacent groups.

In one embodiment of the present specification, R1 to R4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C20 aryloxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C20 arylamino, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C9-C20 aromatic hydrocarbon ring and aliphatic hydrocarbon ring fused ring group, or substituted or unsubstituted C2-C20 heterocyclic group, or form a substituted or unsubstituted C5-C20 ring with each other by combining adjacent groups.

In one embodiment of the present specification, R1 to R4 are the same or different from each other, each independently is hydrogen; deuterium; a C1-C6 alkyl group substituted or unsubstituted with deuterium; cycloalkyl of C3-C20; silyl substituted with C1-C18 alkyl or C6-C20 aryl; an amine group substituted with a C6-C20 aryl group; C6-C20 aryl substituted or unsubstituted with deuterium, C1-C6 alkyl or C6-C20 aryl; or a C2-C20 heterocyclic group substituted or unsubstituted with deuterium, a C1-C6 alkyl group or a C6-C20 aryl group, or with adjacent groups bonded to each other to form a substituted or unsubstituted C5-C20 ring.

In an embodiment of the present specification, R1 to R4 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino 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 phenanthryl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted acridinyl group.

In one embodiment of the present specification, R1 to R4 are the same or different from each other, each independently hydrogen; deuterium; methyl substituted or unsubstituted with deuterium; tert-butyl substituted or unsubstituted with deuterium; silyl group substituted or unsubstituted with 1 or 2 or more substituents selected from deuterium, methyl, isopropyl, tert-butyl and phenyl; an amine group substituted or unsubstituted with one or more substituents selected from deuterium, phenyl and naphthyl; phenyl substituted or unsubstituted with 1 or 2 or more substituents selected from deuterium, methyl, isopropyl, tert-butyl, phenyl and adamantyl; biphenyl substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; phenanthryl substituted or unsubstituted with deuterium; an adamantyl group substituted or unsubstituted with deuterium; tetrahydronaphthyl substituted or unsubstituted with 1 or more substituents selected from deuterium, methyl, and phenyl; a fluorenyl group substituted or unsubstituted with deuterium or methyl; benzofuranyl substituted or unsubstituted with 1 or 2 or more substituents selected from deuterium, methyl, isopropyl, tert-butyl and phenyl; dibenzofuranyl substituted or unsubstituted with 1 or 2 or more substituents selected from deuterium, methyl, isopropyl, tert-butyl, and phenyl; benzothienyl substituted or unsubstituted with 1 or 2 or more substituents selected from deuterium, methyl, isopropyl, tert-butyl and phenyl; dibenzothienyl substituted with 1 or 2 or more substituents selected from deuterium, methyl, isopropyl, tert-butyl and phenyl; a pyridinyl group substituted or unsubstituted with deuterium; benzothiazolyl substituted or unsubstituted with deuterium; carbazolyl substituted or unsubstituted with 1 or more substituents selected from deuterium, methyl, isopropyl or tert-butyl; or an acridinyl group substituted or unsubstituted with 1 or 2 or more substituents selected from deuterium, methyl, isopropyl or tert-butyl.

In one embodiment of the present specification, chemical formula 1 is any one of the following chemical formulas 201 to 203.

[ chemical formula 201]

[ chemical formula 202]

[ chemical formula 203]

In the above-mentioned chemical formulas 201 to 203,

y2 is NR5, O or S,

r5 is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, cy1, X1 to X3, Z, R1 to R4, and R1 to R4 are the same as defined in the above chemical formula 1.

In one embodiment of the present disclosure, Y2 is O or S.

In one embodiment of the present description, Y2 is NR5.

In one embodiment of the present description, R5 is a substituted or unsubstituted aryl.

In one embodiment of the present description, R5 is aryl substituted or unsubstituted with deuterium, alkyl, or deuterated alkyl.

In one embodiment of the present specification, R5 is phenyl, biphenyl, or naphthyl, wherein R5 is substituted or unsubstituted with deuterium, C1-C6 alkyl, or deuterated C1-C6 alkyl.

In one embodiment of the present description, Z is O or S.

In one embodiment of the present specification, the above chemical formula 1 is any one of the following chemical formulas 401 to 406.

In the above-mentioned chemical formulas 401 to 406,

x4 is NR4, O or S,

cy1, Z, R1 to R4 and R1 to R3 are as defined in chemical formula 1 above.

In one embodiment of the present description, Z is NR11.

In one embodiment of the present specification, R11 is a substituted or unsubstituted aryl group, or a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and aliphatic hydrocarbon ring, or is combined with an adjacent R1 or R11 to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R11 is a substituted or unsubstituted C6-C30 aryl group, or a fused ring group of a substituted or unsubstituted C9-C30 aromatic hydrocarbon ring and aliphatic hydrocarbon ring, or is combined with an adjacent R1 or R11 to form a substituted or unsubstituted C5-C30 ring.

In one embodiment of the present specification, R11 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted indanyl group, or a substituted or unsubstituted tetrahydronaphthyl group.

In one embodiment of the present specification, the aryl group of R11 is substituted or unsubstituted with R14 described later.

In one embodiment of the present disclosure, R11 is the following structure, which is the position of the linkage to the above chemical formula 1.

In one embodiment of the present specification, R12 and R13 are the same or different from each other, each independently is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R12 and R13 are the same or different from each other, each independently is a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group, or are combined with each other to form a substituted or unsubstituted fluorene ring.

In one embodiment of the present specification, chemical formula 1 is any one of the following chemical formulas 301 to 304.

[ chemical formula 301]

[ chemical formula 302]

[ chemical formula 303]

[ chemical formula 304]

In the above-mentioned chemical formulas 301 to 304,

y1 is O, S, NR, CR22R23 or SiR22R23,

y1 is either 0 or 1 and,

r14 to R20 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted ring,

r1 'is an integer from 0 to 3, r14 is an integer from 0 to 5, r14' is an integer from 0 to 4,

when r1', r14 and r14' are 2 or more, the substituents in brackets are the same or different from each other,

x1 to X3, R1 to R4 and R1 to R4 are as defined in the above chemical formula 1.

In an embodiment of the present specification, R1 to R4 and R11 to R20 are the same or different from each other, and 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 alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aromatic hydrocarbon ring, a condensed ring group of an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or are combined with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R1 to R4 and R11 to R20 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C6-C60 arylsilyl group, a substituted or unsubstituted C1-C20 alkylamino group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C9-C30 aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a substituted or unsubstituted C2-C30 heterocyclic group, or a substituted or unsubstituted C5-C30 ring combined with each other with the adjacent groups.

In one embodiment of the present specification, R1 to R4 and R11 to R20 are the same or different from each other, each independently is hydrogen; deuterium; an alkyl group substituted or unsubstituted with deuterium; cycloalkyl; a silyl group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, alkyl and aryl, or with 2 or more groups selected from the group consisting of the above; aryl substituted or unsubstituted by 1 or more substituents selected from the group consisting of deuterium and alkyl or by 2 or more groups selected from the group; a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring which are substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium and alkyl groups or with 2 or more substituents selected from the group consisting of deuterium and alkyl groups; a silyl group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, alkyl and aryl, or with 2 or more groups selected from the group consisting of the above; a heterocyclic group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium and alkyl groups or with 2 or more groups selected from the group; or an amino group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or with 2 or more substituents selected from the group, or with adjacent substituents being bonded to each other to form an aromatic hydrocarbon ring which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium and an alkyl group, or with 2 or more substituents selected from the group; an aliphatic hydrocarbon ring substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium and alkyl groups or with 2 or more groups selected from the group; aromatic heterocycles; or an aliphatic heterocyclic ring.

In one embodiment of the present specification, R1 to R3 and R14 are the same or different from each other and are each independently hydrogen, deuterium, a C1-C6 alkyl group substituted or unsubstituted with deuterium, a C3-C20 cycloalkyl group, a C1-C18 alkylsilyl group, or a C6-C20 aryl group substituted or unsubstituted with deuterium.

In an embodiment of the present specification, R1 to R3 and R14 are the same or different from each other, and are each independently hydrogen, deuterium, methyl group substituted or unsubstituted with deuterium, isopropyl group, tert-butyl group, cyclohexyl group, adamantyl group, trimethylsilyl group, or phenyl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, R1 to R3 and R14 to R20 are combined with adjacent substituents to form a ring of Cy2 or Cy3 described below. Specifically, adjacent 2R 1 s, adjacent 2R 2 s, adjacent 2R 3 s, adjacent 2R 14 s, R16 s, and R17 s, or R19 s and R20 s are bonded to each other to form a Cy2 ring or a Cy3 ring described below.

* For carbon condensed with the above chemical formula 1,

m1 is 0 or 1 and,

x7 is O, S, CR, 24R25 or NR28,

r24 to R28 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted ring,

r26 is an integer of 0 to 8, r27 is an integer of 0 to 4,

when r26 and r27 are each 2 or more, the substituents in parentheses are the same or different from each other.

In one embodiment of the present specification, R24 to R28 apply to the description above for R1 to R3 or R14.

In one embodiment of the present specification, R26 is hydrogen, deuterium, or a substituted or unsubstituted C1-C6 alkyl group.

In one embodiment of the present description, R26 is hydrogen, deuterium, or methyl substituted or unsubstituted with deuterium.

In one embodiment of the present disclosure, R26 is 2 or more, and 2 or more of R26 are methyl groups substituted or unsubstituted with deuterium.

In one embodiment of the present specification, 2 or 4 of R26 are methyl groups substituted or unsubstituted with deuterium.

In one embodiment of the present description, 2 or 4 of R26 are methyl groups.

In one embodiment of the present disclosure, cy2 is selected from the following structures.

In the above-described structure, the first and second heat exchangers,

* Is a carbon condensed with the above chemical formula 1.

In one embodiment of the present description, R27 is hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or is combined with adjacent R27 to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R27 is hydrogen, deuterium, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C6-C20 aryl group, or is combined with adjacent R27 to form a substituted or unsubstituted C6-C20 ring.

In one embodiment of the present description, R27 is hydrogen or deuterium.

In one embodiment of the present specification, R24 and R25 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R24 and R25 are the same or different from each other, and are each independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, or phenyl substituted or unsubstituted with deuterium.

In one embodiment of the present description, R24 and R25 are methyl.

In one embodiment of the present description, R28 is a substituted or unsubstituted aryl.

In one embodiment of the present description, R28 is aryl substituted or unsubstituted with deuterium, alkyl, or deuterated alkyl.

In one embodiment of the present specification, R28 is phenyl, biphenyl, or naphthyl, wherein R28 is substituted or unsubstituted with deuterium, C1-C6 alkyl, or deuterated C1-C6 alkyl.

In one embodiment of the present disclosure, R14 is a substituent other than hydrogen and is attached in a position ortho to nitrogen (N). Specifically, the following structure is a part of the above chemical formula 301, and a substituent other than hydrogen (R14 such as a halogen group, cyano group, alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, heterocyclic group, cycloalkyl group, alkylsilyl group, arylsilyl group, arylalkyl group, alkylamino group, arylamino group, and heteroarylamino group) is bonded to one or both of the positions ortho to nitrogen (N), i.e., the positions in the dashed line. In this case, a substituent may be further bonded to the nitrogen (N) at a position meta (meta) or para (para), or a ring may be formed.

In one embodiment of the present specification, R4 is an aryl group substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium and alkyl groups or a substituent formed by joining 2 or more groups selected from the above group, or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium and alkyl groups or a substituent formed by joining 2 or more groups selected from the above group.

In one embodiment of the present specification, R4 is phenyl substituted or unsubstituted with deuterium, C-C10 alkyl, or deuterated C1-C10 alkyl.

In one embodiment of the present specification, R4 is deuterium, methyl, CD ₃ Or tert-butyl substituted or unsubstituted phenyl.

In one embodiment of the present disclosure, Y1 is O, S, NR, CR22R23, or SiR22R23.

In one embodiment of the present disclosure, Y1 is O or S.

In one embodiment of the present specification, R21 applies to the description above for R5, R11 or R28.

In one embodiment of the present specification, R22 and R23 apply to the description above for R12 or R13.

In one embodiment of the present description, y1 is 1.

In one embodiment of the present description, y1 is 0. At this time, - (Y1) _y1 The positions are direct bonds.

In one embodiment of the present specification, R15 to R20 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or are combined with adjacent substituents to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R15 to R20 are the same or different from each other, each independently hydrogen; deuterium; an alkyl group substituted or unsubstituted with deuterium; or an aryl group substituted or unsubstituted with deuterium, alkyl, or deuterated alkyl, or a ring of Cy2 or Cy3 is formed by combining with an adjacent substituent.

In one embodiment of the present specification, R15 to R20 are the same or different from each other, each is independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, or phenyl, or is combined with an adjacent substituent to form a cyclohexane ring, a cyclopentane ring, a benzofuran ring, a benzothiophene ring, or an indole ring.

In an embodiment of the present specification, R1 to R3 are the same or different from each other, each is independently hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted hexahydrocarbazolyl group, a substituted or unsubstituted decahydrobenzocarbazolyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted N-phenylbiphenylamino group, or a substituted or unsubstituted biphenylamino group, or is combined with each other to form a substituted or unsubstituted cyclopentene ring, or a substituted or unsubstituted cyclohexene ring.

In one embodiment of the present specification, R1 to R3 are the same or different from each other, each independently hydrogen; deuterium; methyl substituted or unsubstituted with deuterium; an isopropyl group; a tertiary butyl group; a cyclohexyl group; trimethylsilyl; by deuterium, cyano, fluoro groups, methyl, CD ₃ Phenyl substituted or unsubstituted with isopropyl or tert-butyl; by deuterium, cyano, fluoro groups, methyl, CD ₃ An isopropyl or tert-butyl substituted or unsubstituted biphenyl group; by deuterium, methyl or CD ₃ Substituted or unsubstituted tetrahydronaphthyl; by deuterium, methyl, CD ₃ An isopropyl, tert-butyl, phenyl or trimethylsilyl substituted or unsubstituted hexahydrocarbazolyl group; deuterium, methyl, CD ₃ An isopropyl, tert-butyl, phenyl or trimethylsilyl substituted or unsubstituted decahydrobenzocarbazolyl group; by deuterium, fluoro groups, methyl, CD ₃ A diphenylamino group of an isopropyl, tert-butyl or trimethylsilyl substituted or unsubstituted fused or unfused cyclohexene ring or cyclopentene ring; by deuterium, fluoro, methyl, CD ₃ N-phenylbiphenylamino groups of fused or unfused cyclohexene or cyclopentene rings, substituted or unsubstituted by isopropyl, tert-butyl or trimethylsilyl groups; or by deuterium, fluoro, methyl, CD ₃ A biphenylamino group of an isopropyl-, tert-butyl-or trimethylsilyl-substituted or unsubstituted fused or unfused cyclohexene ring or cyclopentene ring, or adjacent substituents are bonded to each other to form a methyl-substituted or unsubstituted cyclopentene ring, or a methyl-substituted or unsubstituted cyclohexene ring.

In one embodiment of the present description, R3 is a substituent other than hydrogen and R3 is an integer from 1 to 3.

In one embodiment of the present specification, the chemical formula 201 is any one of the following chemical formulas 201-1 to 201-3.

[ chemical formula 201-3]

In the above chemical formulas 201-1 to 201-3, the definition of the substituents is as described above.

In one embodiment of the present specification, the chemical formula 202 is any one of the following chemical formulas 202-1 to 202-3.

[ chemical formula 202-3]

In the above chemical formulas 202-1 to 202-3, the substituents are defined as above.

In one embodiment of the present specification, the chemical formula 203 is any one of the following chemical formulas 203-1 to 203-3.

[ chemical formula 203-3]

In the above chemical formulas 203-1 to 203-3, the definition of the substituents is as described above.

In one embodiment of the present specification, the chemical formula 301 is any one of the following chemical formulas 301-1 to 301-3.

[ chemical formula 301-3]

In the above chemical formulas 301-1 to 301-3, the definition of the substituents is as described above.

In one embodiment of the present specification, cy1 is one selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring, and a substituted or unsubstituted aliphatic heterocyclic ring, or a ring formed by fusing 2 or more rings selected from the above group,

z is O, S or NR11, and the catalyst is,

r1 to R4 and R11 are the same or different from each other and 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 alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylsilyl group, a substituted or unsubstituted arylsilyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted aryl group, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted ring,

the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, halogen groups, cyano groups, alkyl groups, cycloalkyl groups, alkoxy groups, aryloxy groups, amino groups, aryl groups, condensed ring groups of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and heterocyclic groups, or with substituents in which 2 or more of the above substituents are bonded, or without any substituent.

The carbon number of the alkyl group and the alkoxy group is 1 to 10, the carbon number of the cycloalkyl group and the aliphatic hydrocarbon ring is 3 to 30, the carbon number of the aryl group, the aryloxy group and the aromatic hydrocarbon ring is 6 to 30, the carbon number of the alkylsilyl group and the alkylamino group is 1 to 20, the carbon number of the arylsilyl group and the arylamino group is 6 to 30, the carbon number of the condensed ring group of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring is 9 to 30, the carbon number of the aromatic heterocyclic group, the aromatic heterocyclic group and the aliphatic heterocyclic group is 2 to 30, and the aromatic heterocyclic group, the aromatic heterocyclic group and the aliphatic heterocyclic group contain 1 or more of N, O, S and Si.

In one embodiment of the present specification, the chemical formula 1 is any one of the following compounds.

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The substituents of the compound of the above chemical formula 1 may be combined by a method known in the art, and the kind, position or number of the substituents may be changed according to a technique known in the art. For example, the synthesis can be performed by the following synthesis examples.

The conjugation length of the above-mentioned compounds has a close relationship with the energy band gap. Specifically, the longer the conjugate length of the compound, the smaller the energy band gap.

In the present invention, as described above, various substituents are introduced into the core structure, whereby compounds having various energy bandgaps can be synthesized. In the present invention, the HOMO and LUMO levels of the compounds can also be adjusted by introducing various substituents into the core structure of the structure described above.

In addition, by introducing various substituents into the core structure of the structure described above, a compound having the inherent characteristics of the introduced substituents can be synthesized. For example, a substance satisfying the conditions required for each organic layer can be synthesized by introducing substituents mainly used in the hole injection layer substance, the hole transport substance, the light emitting layer substance, and the electron transport layer substance used in manufacturing the organic light emitting device into the above-described core structure.

In addition, the organic light emitting device according to the present invention is characterized by comprising: a first electrode, a second electrode disposed opposite to the first electrode, and 1 or more organic layers disposed between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the polycyclic compound.

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

The compound may be used not only in the vacuum vapor deposition method but also in the solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.

The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure or a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that performs hole injection and hole transport simultaneously, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers or a greater number of organic layers.

In the organic light emitting device of the present invention, the organic layer may include 1 or more layers of a hole blocking layer, an electron transporting layer, an electron injecting layer, and a layer performing electron injection and electron transport at the same time, and the 1 or more layers may include the polycyclic compound of the chemical formula 1.

In the organic light emitting device of the present invention, the organic layer may include 1 or more layers of a hole injection layer, a hole transport layer, an electron blocking layer, and a layer that performs hole injection and hole transport at the same time, and the 1 or more layers may include the polycyclic compound of chemical formula 1.

In another embodiment, the organic layer includes a light emitting layer including the polycyclic compound of chemical formula 1. As an example, the polycyclic compound of the above chemical formula 1 may be included as a dopant of the light emitting layer.

The maximum light emission peak of the light emitting layer including the polycyclic compound of chemical formula 1 described above is 380nm to 500nm. That is, the light-emitting layer is a blue light-emitting layer.

As another example, the light emitting layer including the polycyclic compound of the above chemical formula 1 includes the polycyclic compound of the above chemical formula 1 as a dopant, and may include a fluorescent host and a phosphorescent host.

In another embodiment, the light emitting layer including the polycyclic compound of the above chemical formula 1 includes the polycyclic compound of the above chemical formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and may include other organic compounds, metals, or metal compounds as dopants.

As another example, the light emitting layer including the polycyclic compound of the above chemical formula 1 includes the polycyclic compound of the above chemical formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and may be used together with an iridium (Ir) dopant.

According to an embodiment of the present specification, the organic layer includes a light emitting layer including the polycyclic compound as a dopant of the light emitting layer and a compound having the following chemical formula H as a host of the light emitting layer.

[ chemical formula H ]

In the above-mentioned chemical formula H,

l21 and L22 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar21 and Ar22 are the same as or different from each other, each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

r201 and R202 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

n202 is an integer of 0 to 7, and when n202 is 2 or more, R202 is the same or different from each other.

In one embodiment of the present specification, L21 and L22 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted C6-C30 monocyclic or polycyclic arylene, or a substituted or unsubstituted C2-C30 monocyclic or polycyclic heteroarylene.

In one embodiment of the present specification, L21 and L22 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted C6-C20 monocyclic or polycyclic arylene, or a substituted or unsubstituted C2-C20 monocyclic or polycyclic heteroarylene.

In one embodiment of the present specification, L21 and L22 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted 2-valent dibenzofuranyl group, or a substituted or unsubstituted 2-valent dibenzothienyl group.

In an embodiment of the present specification, L21 and L22 are the same or different from each other, and are each independently a direct bond, a deuterium-substituted or unsubstituted phenylene group, a deuterium-substituted or unsubstituted biphenylene group, a deuterium-substituted or unsubstituted naphthylene group, a deuterium-substituted or unsubstituted 2-valent dibenzofuranyl group, or a deuterium-substituted or unsubstituted 2-valent dibenzothienyl group.

In one embodiment of the present specification, L21 and L22 are the same or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted with deuterium, or a naphthylene group substituted or unsubstituted with deuterium.

In one embodiment of the present description, one of L21 and L22 is a direct bond.

In one embodiment of the present disclosure, L21 is a direct bond.

In one embodiment of the present disclosure, L22 is a direct bond.

In an embodiment of the present specification, ar21 and Ar22 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In an embodiment of the present specification, ar21 and Ar22 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

In an embodiment of the present specification, ar21 and Ar22 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

In an embodiment of the present specification, ar21 and Ar22 are the same or different from each other and are each independently 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 anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenacyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted naphthobenzothienyl group.

In one embodiment of the present specification, ar21 and Ar22 are the same or different from each other, each independently is phenyl substituted or unsubstituted with deuterium, or a C6-C20 monocyclic or polycyclic aryl group; biphenyl substituted or unsubstituted with deuterium, or a C6-C20 monocyclic or polycyclic aryl group; naphthyl substituted or unsubstituted with a C6-C20 monocyclic or polycyclic aryl group; dibenzofuranyl substituted or unsubstituted with deuterium, or a C6-C20 monocyclic or polycyclic aryl group; a naphthobenzofuranyl group substituted or unsubstituted with deuterium, or a C6-C20 monocyclic or polycyclic aryl group; dibenzothienyl substituted with deuterium, or a C6-C20 monocyclic or polycyclic aryl group; or a naphthobenzothienyl group substituted or unsubstituted with deuterium, or a C6-C20 monocyclic or polycyclic aryl group.

In one embodiment of the present specification, ar21 and Ar22 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, a terphenyl group, a naphthyl group substituted or unsubstituted with deuterium, a phenanthryl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a dibenzothiophenyl group, or a naphthobenzothiophenyl group.

In one embodiment of the present specification, either Ar21 and Ar22 is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heterocyclic group.

In one embodiment of the present disclosure, ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted heterocyclic group.

In one embodiment of the present disclosure, ar21 is a substituted or unsubstituted heterocyclic group, and Ar22 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R201 is hydrogen, deuterium, a substituted or unsubstituted C6-C30 monocyclic or polycyclic aryl group, or a substituted or unsubstituted C2-C30 monocyclic or polycyclic heterocyclic group.

In one embodiment of the present specification, R201 is hydrogen, deuterium, a substituted or unsubstituted C6-C20 monocyclic or polycyclic aryl group, or a substituted or unsubstituted C2-C20 monocyclic or polycyclic heterocyclic group.

In one embodiment of the present specification, R201 is hydrogen, deuterium, a substituted or unsubstituted C6-C20 monocyclic to tetracyclic aryl group, or a substituted or unsubstituted C6-C20 monocyclic to tetracyclic heterocyclyl group.

In one embodiment of the present specification, R201 is hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted phenacyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted dibenzothienyl, or substituted or unsubstituted naphthobenzothienyl.

In one embodiment of the present description, R201 is hydrogen; deuterium; phenyl substituted or unsubstituted with deuterium, or a C6-C20 monocyclic or polycyclic aryl group; biphenyl substituted or unsubstituted with a C6-C20 monocyclic or polycyclic aryl group; naphthyl substituted or unsubstituted with deuterium, or a C6-C20 monocyclic or polycyclic aryl group; dibenzofuranyl substituted or unsubstituted with deuterium, or a C6-C20 monocyclic or polycyclic aryl group; a naphthobenzofuranyl group substituted or unsubstituted with deuterium, or a C6-C20 monocyclic or polycyclic aryl group; dibenzothienyl substituted with deuterium, or a C6-C20 monocyclic or polycyclic aryl group; or a naphthobenzothienyl group substituted or unsubstituted with deuterium, or a C6-C20 monocyclic or polycyclic aryl group.

In one embodiment of the present description, R201 is hydrogen; deuterium; phenyl substituted or unsubstituted with deuterium, phenyl or naphthyl; a biphenyl group; naphthyl substituted or unsubstituted with deuterium, phenyl or naphthyl; dibenzofuranyl; naphthobenzofuranyl; dibenzothienyl; or naphtobenzothienyl.

According to an embodiment of the present disclosure, R202 is hydrogen or deuterium.

According to an embodiment of the present disclosure, 4 or more of R202 are deuterium.

According to one embodiment of the present disclosure, R202 is hydrogen.

According to one embodiment of the present disclosure, R202 is deuterium.

In one embodiment of the present specification, when the compound of formula H is substituted with deuterium, hydrogen at a substitutable position is substituted with deuterium by 30% or more. In another embodiment, the hydrogen at the substitutable position of the structure of formula H above is substituted by deuterium by more than 40%. In another embodiment, the hydrogen at the substitutable position of the structure of formula H above is substituted by deuterium by 60% or more.

In another embodiment, the hydrogen at the substitutable position of the structure of formula H above is replaced by deuterium by more than 80%. In another embodiment, the hydrogen at the substitutable position of the structure of formula H above is substituted 100% with deuterium.

In one embodiment of the present specification, the compound of formula H is any one selected from the following compounds.

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In one embodiment of the present disclosure, the light emitting layer includes the polycyclic compound of formula 1 as a dopant of the light emitting layer, and includes the compound of formula H as a host of the light emitting layer.

In an embodiment of the present disclosure, the light emitting layer includes a host and a dopant, and the host and the dopant are included in a weight ratio of 99:1 to 1:99, preferably in a weight ratio of 99:1 to 70:30, and more preferably in a weight ratio of 99:1 to 90:10.

According to an embodiment of the present disclosure, the organic layer includes a light-emitting layer including 1 or more kinds of host.

According to an embodiment of the present disclosure, the organic layer includes a light-emitting layer including 2 or more kinds of mixed hosts.

According to an embodiment of the present specification, 1 or more of the 2 or more kinds of mixed bodies are the compounds of the chemical formula H.

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

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

The structure of the organic light emitting device of the present invention may have the structures shown in (1) to (18) below, but is not limited thereto.

(1) Anode/hole transport layer/light emitting layer/cathode

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

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

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

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

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

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

(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode

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

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

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

(12) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode

(13) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode

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

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

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

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

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

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

Fig. 1 illustrates a structure of an organic light-emitting device in which a light-emitting layer 3 and a cathode 4 are sequentially stacked on a substrate 1 and an anode 2. In the structure as described above, the polycyclic compound of the above chemical formula 1 may be contained in the above light emitting layer 3.

Fig. 2 illustrates a structure of an organic light-emitting device in which a first hole injection layer 5, a second hole injection layer 6, a hole transport layer 7, an electron blocking layer 8, a light-emitting layer 3, a first electron transport layer 9, a second electron transport layer 10, an electron injection layer 11, and a cathode 4 are sequentially stacked on a substrate 1 and an anode 2. In the structure as described above, the polycyclic compound of the above chemical formula 1 may be contained in the above light emitting layer 3.

For example, the organic light emitting device according to the present invention may be manufactured as follows: PVD (physical vapor deposition) such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation) is used to deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, and then an organic layer including 1 or more layers selected from a hole injection layer, a hole transport layer, a layer in which hole transport and hole injection are performed simultaneously, a light emitting layer, an electron transport layer, an electron injection layer, and a layer in which electron transport and electron injection are performed simultaneously is formed on the anode, and then a substance usable as a cathode is deposited on the organic layer to manufacture the anode. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and the like, but is not limited thereto, and may have a single-layer structure. The organic layer may be formed into a smaller number of layers by a solvent process (solvent process) other than vapor deposition, such as spin coating, dip coating, knife coating, screen printing, ink jet printing, or thermal transfer printing, using various polymer materials.

The anode is an electrode for injecting holes, and is preferably a substance having a large work function as an anode substance in order to allow holes to 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, and alloys thereof; metal oxides such as zinc Oxide, indium Tin Oxide (ITO), and Indium zinc Oxide (IZO, indium Zinc Oxide); znO of Al or SnO ₂ A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.

The above mentioned yinThe electrode is an electrode for injecting electrons, and as a cathode material, a material having a small work function is generally preferred in order to facilitate injection of 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 LiO ₂ And/or Al, but is not limited thereto.

The hole injection layer is a layer that functions to smooth injection of holes from the anode to the light-emitting layer, and may have a single-layer or multi-layer structure. The hole-injecting substance is a substance that can well receive holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer. The thickness of the hole injection layer may be 1nm to 150nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the degradation of the hole injection characteristic can be prevented, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the increase of the driving voltage for improving the migration of holes can be prevented. In one embodiment of the present specification, the hole injection layer has a multilayer structure of 2 or more layers.

The hole transport layer can function to smooth the transport of 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 a substance having a large mobility to the holes is suitable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.

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

An electron blocking layer may be disposed between the hole transport layer and the light emitting layer. The electron blocking layer may use the spiro compound described above or materials known in the art.

The light-emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxy-quinoline aluminum complex (Alq ₃ ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

Examples of the host material of the light-emitting layer include an aromatic condensed ring derivative and a heterocyclic compound. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, etc., but are not limited thereto.

When the light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent substance such as PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonide), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium, bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) irium), tris (1-phenylquinoline) iridium), ptOEP (octaethylporphyrin platinum, platinum octaethylporphyrin), or Alq may be used ₃ (tFluorescent substances such as ris (8-hydroxyquinoline) aluminum, tris (8-hydroxyquinoline) aluminum, etc., but are not limited thereto. When the light emitting layer emits green light, ir (ppy) can be used as a light emitting dopant ₃ Phosphorescent substances such as (factris (2-phenylpyridine) iridium, planar tris (2-phenylpyridine) iridium), or Alq ₃ Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum), but are not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, (4, 6-F ₂ ppy) ₂ Examples of the fluorescent substance include, but are not limited to, phosphorescent substances such as Irpic, fluorescent substances such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers.

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

The electron transport layer plays a role in facilitating electron transport, and may have a single-layer or multi-layer structure. The electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high mobility of electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq ₃ But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The thickness of the electron transport layer may be 1nm to 50nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the degradation of the electron transport property can be prevented, and when it is 50nm or less, there is an advantage that the increase of the driving voltage for the purpose of improving the electron transfer can be prevented when the thickness of the electron transport layer is too thick. In one embodiment of the present disclosure, the electron transport layer has a multilayer structure of 2 or more layers, and the electron transport layer adjacent to the cathode contains an n-type dopant.

The electron injection layer can perform a function of smoothly injecting electrons. As the electron injecting substance, the following compounds are preferable: has an electron transporting ability, an electron injecting effect from a cathode, an excellent electron injecting effect to a light emitting layer or a light emitting material, a prevention of migration of excitons generated in the light emitting layer to a hole injecting layer, and a film forming abilityA compound excellent in strength. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.

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

The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed generally under the same conditions as those of the hole injection layer. Specifically, there areThe diazole derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.

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

Modes for carrying out the invention

In the following, examples, comparative examples, and the like will be described in detail for the purpose of specifically describing the present specification. 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. Examples and comparative examples of the present description are provided to more fully illustrate the present description to those skilled in the art.

Synthesis example

Synthesis example 1 Synthesis of Compound A-7

1) Synthesis of B-4

25g (1 eq.) of B-1, 20g (1.1 eq.) of B-2, 33.3g (2 eq.) of K are combined under nitrogen ₂ CO ₃ 1.4g (0.01 eq.) of tetrakis (triphenylphosphine) palladium are added to 450ml of 1, 4-bisAfter the alkane (dioxane) and 150mL of distilled water, the mixture was stirred at reflux for 2 hours. After the reaction was completed, the organic layer was extracted, and intermediate B-3 was obtained without further purification. (MS [ M+H) ] ⁺ ＝233)

Tf of intermediate B-3, 22.3ml (1.1 eq.) without purification ₂ O (triflic anhydride) and 15.5g (1.05 eq) of DMAP (4-dimethylaminopyridine) were added to 600ml of chloroform and reacted at room temperature for 3 hours. After the completion of the reaction, the organic layer was extracted, and the solution was removed, whereby 31.6g of intermediate B-4 was obtained by column chromatography (eluent): ethyl acetate/hexane (hexane). (yield 72%).

2) Synthesis of B-6

25g (1 eq.) of B-4, 33.9g (1.1 eq.) of B-5, 0.79g (0.02 eq.) of Pd (dba) are combined under nitrogen ₂ (Tris (dibenzylideneacetone) dipalladium (0), tris (dibenzylideneacetone) dipalladium (0)), 1.3g (0.04 eq.) of Xphos (2-Dicyclohexylphosphino-2 ',4',6 '-triisocyclopropylphosphinyl, 2-Dicyclohexylphosphino-2',4',6'Triisopropylbiphenyl), 67g (3 equivalents) of cesium carbonate was added to 300ml of xylene, and the mixture was stirred under reflux for 12 hours. After the completion of the reaction, the organic layer was extracted, and the solvent was removed, whereby 31.9g of intermediate B-6 was obtained by column chromatography (eluent: ethyl acetate/hexane). (yield 68%). MS [ M+H ]] ⁺ ＝685

3) Synthesis of B-8

25g (1 eq.) of B-6, 14.3g (1.1 eq.) of B-7, 15.5 (2 eq.) of potassium phosphate, 0.19g (0.01 eq.) of bis (tri-tert-butylphosphine) palladium (0) are added to 90ml of 1, 4-di under nitrogenAfter the alkane and 30mL of distilled water, the mixture was stirred at reflux for 4 hours. After the completion of the reaction, the organic layer was extracted, and 22g of intermediate B-8 was obtained by recrystallization (yield: 71%). MS [ M+H ]] ⁺ ＝848

4) Synthesis of A-7

20g (1 equivalent) of B-8, 12g (1.3 equivalent) of boron triiodide were added to 150ml of chlorobenzene under nitrogen atmosphere, and stirred at 110℃for 3 hours. After the completion of the reaction, the organic layer was extracted, and 6.7g of Compound A-7 was obtained by recrystallization (yield: 37%). MS [ M+H ]] ⁺ ＝856

Synthesis example 2 Synthesis of Compound A-8

1) Synthesis of B-13

15g (1 eq.) of B-10, 33.5g (1.05 eq.) of B-9, 0.4g (0.01 eq.) of bis (tri-tert-butylphosphine) palladium (0), 10.5g (1.5 eq.) of tert-butanol are reacted under nitrogenSodium (sodium-butoxide) was added to 300ml of xylene, followed by stirring under reflux for 2 hours. After the completion of the reaction, the organic layer was extracted, and the solvent was removed, whereby 34.5g of intermediate B-11 was obtained by recrystallization. (yield 84%). MS [ M+H ]] ⁺ ＝562

By the same method as the synthesis of Compound B-8 of Synthesis example 1, 30g of B-11 and 14.4g of B-12 were used, thereby obtaining 23.6g of intermediate B-13. (yield 67%). MS [ M+H ] ] ⁺ ＝661

2) Synthesis of A-8

By the same method as the synthesis of Compound A-7 of Synthesis example 1, 20g of B-13 was used, thereby obtaining 6.3g of Compound A-8. (yield 31%). MS [ M+H ]] ⁺ ＝669

Synthesis example 3 Synthesis of Compound A-12

1) Synthesis of B-17

By the same procedure as in the synthesis of Compound B-11 of Synthesis example 2, 15g of B-10 and 31.6g of B-14 were used, thereby obtaining 34.4g of intermediate B-15. (yield 88%). MS [ M+H ]] ⁺ ＝536

By the same method as the synthesis of Compound B-8 of Synthesis example 1, 30g of B-15 and 24.1g of B-16 were used, thereby obtaining 29.8g of intermediate B-17. (yield 71%). MS [ M+H ]] ⁺ ＝750

2) Synthesis of A-12

By the same method as the synthesis of Compound A-7 of Synthesis example 1, 25g of B-17 was utilized, thereby obtaining 5.6g of Compound A-12. (yield 22%). MS [ M ]H] ⁺ ＝758

Synthesis example 4 Synthesis of Compound A-16

1) Synthesis of B-21

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By the same method as the synthesis of Compound B-11 of Synthesis example 2, using 15g of B-10 and 34.4g of B-18, purification was performed by column chromatography (eluent: ethyl acetate/hexane) to obtain 33.1g of intermediate B-19. (yield 79%). MS [ M+H ]] ⁺ ＝573

By the same procedure as in the synthesis of Compound B-8 of Synthesis example 1, 30g of B-19 and 27.2g of B-20 were used, thereby obtaining 31.4g of intermediate B-21. (yield 68%). MS [ M+H ] ] ⁺ ＝883

2) Synthesis of A-16

By the same method as the synthesis of Compound A-7 of Synthesis example 1, 25g of B-21 was utilized, thereby obtaining 7.3g of Compound A-16. (yield 29%). MS [ M+H ]] ⁺ ＝891

Synthesis example 5 Synthesis of Compound A-18

1) Synthesis of B-25

By the same procedure as in the synthesis of Compound B-11 of Synthesis example 2, 15g of B-10 and 29.9g of B-22 were used, thereby obtaining 33.4g of intermediate B-23. (yield 89%). MS [ M+H ]] ⁺ ＝514

By the same method as the synthesis of Compound B-8 of Synthesis example 1, 25g of B-23 and 22.8g of B-24 were used, thereby obtaining 27.6g of intermediate B-25. (yield 73%). MS [ M+H ]] ⁺ ＝778

2) Synthesis of A-18

By the same method as the synthesis of Compound A-7 of Synthesis example 1, 23g of B-25 was utilized, thereby obtaining 5.8g of Compound A-18. (yield 25%). MS [ M+H ]] ⁺ ＝786

Synthesis example 6 Synthesis of Compound A-10

1) Synthesis of B-29

By the same procedures as those conducted for the synthesis of compound B-11 of synthesis example 2, 30g of B-1, 42.7g of B-26, and 27.8g (2 equivalents) of sodium t-butoxide were used, whereby 46.6g of intermediate B-27 was obtained. (yield 79%). MS [ M+H ]] ⁺ ＝408

By the same procedure as in the synthesis of compound B-27 of Synthesis example 6, using 20g of B-27 and 11.6g of B-28, intermediate B-29 was obtained without purification. MS [ M+H ] ] ⁺ ＝597

2) Synthesis of B-32

By the same method as the synthesis of Compound B-4 of Synthesis example 1, the total amount of synthesis was taken advantage of using B-29 without purification, thereby obtaining 22.2g of intermediate B-30. (yield 62% based on B-27).

By the same method as the synthesis of Compound B-8 of Synthesis example 1, 20g of B-30 and 10.1g of B-31 were used, thereby obtaining 15.1g of intermediate B-32. (yield 71%). MS [ M+H ]] ⁺ ＝773

3) Synthesis of A-10

By the same method as the synthesis of Compound A-7 of Synthesis example 1, 14g of B-32 was utilized, thereby obtaining 2.5g of Compound A-10. (yield 18%). MS [ M+H ]] ⁺ ＝781

Synthesis example 7 Synthesis of Compound A-17

1) Synthesis of B-35

By the same procedure as in the synthesis of compound B-27 of Synthesis example 6, using 23g of B-27 and 19.9g of B-33, intermediate B-34 was obtained without purification. MS [ M+H ]] ⁺ ＝707

By the same method as the synthesis of Compound B-4 of Synthesis example 1, the total amount of synthesis was taken advantage of using B-34 without purification, thereby obtaining 28g of intermediate B-35. (yield 59% based on B-27).

2) Synthesis of A-17

By the same method as the synthesis of Compound B-8 of Synthesis example 1, 25g of B-35 and 11g of B-36 were used, thereby obtaining 18.7g of intermediate B-37. (yield 70%). MS [ M+H ] ] ⁺ ＝899

By the same method as the synthesis of Compound A-7 of Synthesis example 1, 17g of B-37 was utilized, thereby obtaining 4.5g of Compound A-17. (yield 26%). MS [ M+H ]] ⁺ ＝908

Synthesis example 8 Synthesis of Compound A-14

1) Synthesis of B-41

By the same method as the synthesis of Compound B-27 of Synthesis example 615g of B-1 and 14.1g of B-38 were used, whereby 17.8g of intermediate B-39 was obtained. (yield 83%). MS [ M+H ]] ⁺ ＝296

By the same procedure as in the synthesis of compound B-27 of Synthesis example 6, using 16g of B-39 and 20.3g of B-40, intermediate B-41 was obtained without purification. MS [ M+H ]] ⁺ ＝617

2) Synthesis of B-44

By the same procedure as in the synthesis of Compound B-4 of Synthesis example 1, the total amount of synthesis was taken using B-41 without purification, thereby obtaining 26.2g of intermediate B-42. (yield 65% based on B-39).

By the same procedure as in the synthesis of Compound B-8 of Synthesis example 1, 25g of B-42 and 14.5g of B-43 were used, thereby obtaining 19.7g of intermediate B-44. (yield 68%). MS [ M+H ]] ⁺ ＝868

3) Synthesis of A-14

By the same method as the synthesis of Compound A-7 of Synthesis example 1, 18g of B-44 was utilized, thereby obtaining 5.3g of Compound A-14. (yield 29%). MS [ M+H ] ] ⁺ ＝876

Synthesis example 9 Synthesis of Compound A-15

1) Synthesis of B-48

By the same procedure as in the synthesis of Compound B-27 of Synthesis example 6, 15g of B-1 and 14.8g of B-45 were used, thereby obtaining 18.8g of intermediate B-46. (yield 85%). MS [ M+H ]] ⁺ ＝306

By synthesis with Compound B-27 of Synthesis example 6The same procedure, using 17g of B-46, 19.6g of B-47, gives intermediate B-48 without purification. MS [ M+H ]] ⁺ ＝605.33

2) Synthesis of B-51

By the same method as the synthesis of Compound B-4 of Synthesis example 1, the total amount of synthesis was taken with B-48 without purification, thereby obtaining 24.6g of intermediate B-49. (yield 60% based on B-46).

By the same method as the synthesis of Compound B-8 of Synthesis example 1, 23g of B-49 and 11g of B-50 were used, thereby obtaining 16.1g of intermediate B-51. (yield 66%). MS [ M+H ]] ⁺ ＝782

3) Synthesis of A-15

By the same method as the synthesis of Compound A-7 of Synthesis example 1, 15g of B-51 was utilized, thereby obtaining 3.8g of Compound A-15. (yield 25%). MS [ M+H ]] ⁺ ＝790

Synthesis example 10 Synthesis of Compound A-13

1) Synthesis of B-54

By the same method as the synthesis of Compound B-11 of Synthesis example 2, 15g of B-53 and 25.7g of B-52 were used, thereby obtaining 25.7g of intermediate B-54. (yield 74%). MS [ M+H ] ] ⁺ ＝517

2) Synthesis of A-13

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24.1g of intermediate B-56 was obtained by the same method as the synthesis of Compound B-8 of Synthesis example 1, using 24g of B-54 and 17.2g of B-55. (yield 75%). MS [ M+H ]] ⁺ ＝691

By the same method as the synthesis of Compound A-7 of Synthesis example 1, 22g of B-56 was used, whereby 4.4g of Compound A-13 was obtained. (yield 20%). MS [ M+H ]] ⁺ ＝699

Synthesis example 11 Synthesis of Compound A-9

1) Synthesis of B-60

Purification by recrystallization was carried out in the same manner as in the synthesis of Compound B-3 of Synthesis example 1 using 30g of B-1 and 36.9g of B-57, to obtain 37.8g of intermediate B-58. (yield 83%). MS [ M+H ]] ⁺ ＝315

After 35g (1 eq) of B-58, 42.7g (4 eq) of B-59, 40g (2 eq) of potassium carbonate were added to 260ml of N, N-dimethylacetamide under nitrogen atmosphere, the mixture was heated and stirred at 150℃for 5 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature, and 300mL of distilled water was added. After stirring at room temperature for 1 hour, the resulting solid was filtered. The solid was washed with ethanol, whereby 13.5g of intermediate B-60 was obtained. (yield 31%). MS [ M+H ]] ⁺ ＝391

2) Synthesis of B-62

By the same method as the synthesis of Compound B-8 of Synthesis example 1, 13g of B-60 and 14.6g of B-61 were used, thereby obtaining 15.1g of intermediate B-62. (yield 72%). MS [ M+H ] ] ⁺ ＝629

3) Synthesis of A-9

By the same method as the synthesis of Compound A-7 of Synthesis example 1, 14g of B-62 was used, whereby 2.7g of Compound A-9 was obtained. (yield 19%). MS [ M+H ]] ⁺ ＝637

Synthesis example 12 Synthesis of Compound A-11

1) Synthesis of B-67

By the same procedure as in the synthesis of Compound B-11 of Synthesis example 2, 15g of B-1 and 21.2g of B-63 were used, thereby obtaining 23.5g of intermediate B-64. (yield 80%). MS [ M+H ]] ⁺ ＝406

22g (1 eq.) of B-64, 8.5g (1.05 eq.) of B-65, 0.3g (0.01 eq.) of bis (tri-tert-butylphosphine) palladium (0), 10.4g (2 eq.) of sodium tert-butoxide were added to 250ml of xylene under nitrogen atmosphere, and then stirred under reflux for 4 hours. After the completion of the reaction, 17.2g (1.1 eq) of B-66 and an additional 0.3g (0.01 eq) of bis (tri-t-butylphosphine) palladium (0) were added, followed by stirring under reflux for 10 hours. After the end of the final reaction, the organic layer was extracted and the solvent was removed to obtain intermediate B-67 without purification. MS [ M+H ]] ⁺ ＝727

2) Synthesis of B-70

By the same method as the synthesis of Compound B-4 of Synthesis example 1, the total amount of synthesis was taken with B-67 without purification, thereby obtaining 23.7g of intermediate B-68. (based on B-64, yield 51%).

By the same procedures as those conducted for the synthesis of Compound B-8 of Synthesis example 1, 22g of B-68 and 11.1g of B-69 were used, whereby 16.3g of intermediate B-70 was obtained. (yield 65%). MS [ M+H ]] ⁺ ＝976

3) Synthesis of A-11

By the same method as the synthesis of Compound A-7 of Synthesis example 1, 54g of B-70 was used, whereby 3.3g of Compound A-11 was obtained. (yield 22%). MS [ M+H ]] ⁺ ＝984

Synthesis example 13 Synthesis of Compound A-19

1) Synthesis of B-74

By the same method as the synthesis of Compound B-11 of Synthesis example 2, 15g of B-1 and 15.9g of B-71 were used, thereby obtaining 18.7g of intermediate B-72. (yield 77%). MS [ M+H ]] ⁺ ＝336

By the same procedure as in the synthesis of compound B-67 of Synthesis example 12, using 18g of B-72, 8.4g of B-65, and 19.1g of B-73, intermediate B-74 was obtained without purification. MS [ M+H ]] ⁺ ＝691

2) Synthesis of B-76

By the same method as the synthesis of Compound B-4 of Synthesis example 1, the total amount of synthesis was taken with B-74 without purification, thereby obtaining 20.7g of intermediate B-75. (yield 47% based on B-72).

By the same procedures as those conducted for the synthesis of Compound B-8 of Synthesis example 1, 19g of B-75 and 8.5g of B-36 were used, whereby 14.5g of intermediate B-76 was obtained. (yield 71%). MS [ M+H ] ] ⁺ ＝883

2) Synthesis of A-19

By the same method as the synthesis of Compound A-7 of Synthesis example 1, 13g of B-76 was utilized, thereby obtaining 4.3g of Compound A-19. (yield 33%). MS [ M+H ]] ⁺ ＝891

Experimental example 1]

For the above compounds, HOMO levels, LUMO levels, and singlet and triplet energy levels based on absorption (absorption) states, and singlet vibrator intensities (h) (radiative transition probability, f) of the molecules were calculated using the TD-DFT (B3 LyP) method/6-31G-based group method. The calculation results are shown in table 1 below.

TABLE 1

	Comparative example 1	Comparative example 2	Comparative example 3	Comparative example 4	Example 1
						Compounds of formula (I)	X-1	X-2	X-3	X-3	A-1
HOMO(eV)	4.74	5.00	5.00	4.79	4.79
						LUMO(eV)	1.07	1.82	1.78	1.52	2.16
S1(eV)	3.14	2.78	2.80	2.86	2.37
						T1(eV)	0.49	2.01	2.05	2.12	1.36
f	0.204	0.319	0.279	0.379	0.463
							Example 2	Example 3	Example 4	Example 5	Example 6
Compounds of formula (I)	A-2	A-3	A-4	A-5	A-6
						HOMO(eV)	4.72	4.53	4.71	5.16	5.28
LUMO(eV)	2.15	1.72	2.11	2.38	2.38
						S1(eV)	2.34	2.52	2.36	2.53	2.64
T1(eV)	1.29	1.59	1.33	1.43	1.50
						f	0.525	0.464	0.542	0.452	0.459

The radiation transition probability (f) is calculated as a scale showing fluorescence quantum efficiency by the following formula. The larger the radiation transition probability (f) value, the higher the luminous efficiency.

Vibrator strength

V is in S ^-1 Frequency of (2)

ε (v) is the unit M ^-1 cm ^-1 Molar extinction coefficient of (2)

The triplet energies of the compounds a-1 to a-6 represented by the above chemical formula 1 have lower values when compared with the comparative example compounds X-1 to X-4, and thus triplet quenching is suppressed, so that the device lifetime of the organic light emitting device including the compound represented by the above chemical formula 1 under a host-dopant system is increased.

In addition, the radiation transition probabilities (f) of the compounds A-1 to A-6 represented by the above chemical formula 1 have higher values than those of the comparative example compounds X-1 to X-4, and thus higher device efficiency can be expected based on computational chemistry.

< experimental example 2: device example ]

Example 7.

ITO (indium tin oxide) toThe glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.

On the ITO transparent electrode prepared as described above, the following HI-A and LG-101 were used as the respective componentsAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, HT-A as described below is added +. >Vacuum deposition is performed to form a hole transport layer. On the hole transport layer, HT-B as described below is added +.>Vacuum vapor deposition is performed to form an electron suppression layer. Next, on the electron-inhibiting layer, 3wt% of compound A-1 as a light-emitting dopant was added to the total weight of the light-emitting layer, and the following BH-A as a host was added->And vacuum vapor deposition is performed to the thickness of the substrate to form a light-emitting layer. Then, on the above light-emitting layer, the following compound ET-A as the first electron transport layer was added +.>Vacuum deposition was performed, and then E was as followsT-B and LiQ were vacuum evaporated in a weight ratio of 1:1, whereby +.>An electron transport layer is formed by the thickness of (a). Vacuum evaporating LiQ on the electron transport layer, and adding +.>Vacuum deposition is performed from the thickness of (a) to form an electron injection layer. On the electron injection layer, by +.>Aluminum and silver were evaporated at a weight ratio of 10:1, on which aluminum was added +.>And vapor deposition is performed to form a cathode.

In the above process, the vapor deposition rate of the organic matter is maintainedAluminum maintenance of cathode->During vapor deposition, the vacuum degree is maintained at 1X 10-7 to 5X 10-8 Torr, thereby manufacturing an organic light-emitting device. / >

Examples 8 to 25.

In example 8 above, organic light-emitting devices of examples 8 to 25 were produced in the same manner as in example 7, except that the host and dopant compounds described in table 2 below were used as the light-emitting layer material instead.

Comparative examples 7 to 14.

In example 7 above, organic light-emitting devices of comparative examples 7 to 14 were produced in the same manner as in example 7, except that the host and dopant compounds described in table 2 below were used as the light-emitting layer material instead.

The organic light-emitting devices of the above examples and comparative examples were measured for application of 10mA/cm ² Voltage at current density, efficiency (cd/A) and application of 20mA/cm ² Life (T) at current density (T) ₉₅ ) The results are shown in table 2 below. At this time, the current efficiency (cd/A) is shown as a ratio based on the compound X-8, T ₉₅ Will "will have a current density of 20mA/cm ² The time required for the luminance to decrease to 95% at the initial luminance of 100% below is shown as a ratio based on the compound X-8.

TABLE 2

When examples 7 to 13 are compared with comparative examples 7 and 8, it can be confirmed that the life level of the compound represented by the above chemical formula 1 is improved by 10 to 20% when using a compound containing benzothiophene (benzothiophene) as compared with the case of using X-8 as a dopant.

When examples 14 to 10 are compared with comparative examples 9, 10 and 14, it can be confirmed that the life level of the compound represented by the above chemical formula 1 is improved by 10 to 40% when using a compound containing benzofuran (benzofuran) as compared with the case where X-7 or X-10 is used as a dopant.

When comparing examples 21 to 25 with comparative examples 11 and 13, it was confirmed that the life level of the compound represented by the above chemical formula 1 was improved by 10 to 15% in most cases, particularly, by a significant improvement when compared with the X-9 compound, in the case of using the compound containing indole (indole), pyrrole (pyrrrole) and azole (azole) containing nitrogen.

Through the above-described various experiments, it was confirmed that the efficiency of the compound represented by the above chemical formula 1 was slightly improved and excellent performance of long life was exhibited.

Claims

1. A polycyclic compound of the following chemical formula 1:

[ chemical formula 1]

In the chemical formula 1 described above, a compound having the formula,

cy1 is one selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring, and a substituted or unsubstituted aliphatic heterocyclic ring, or a ring formed by fusing 2 or more rings selected from the group,

z is O, S, NR, CR12R13 or SiR12R13,

2. The polycyclic compound according to claim 1, wherein the chemical formula 1 is any one of the following chemical formulas 101 to 103:

[ chemical formula 101]

[ chemical formula 102]

[ chemical formula 103]

In the chemical formulas 101 to 103 described above,

x4 is NR4, O or S,

cy1, Z, R1 to R4 and R1 to R3 are as defined in the chemical formula 1.

3. The polycyclic compound according to claim 1, wherein the chemical formula 1 is any one of the following chemical formulas 201 to 203:

[ chemical formula 201]

[ chemical formula 202]

[ chemical formula 203]

In the chemical formulas 201 to 203 described above,

y2 is NR5, O or S,

r5 is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, a condensed ring group of substituted or unsubstituted aromatic hydrocarbon ring and aliphatic hydrocarbon ring, or substituted or unsubstituted heterocyclic group,

x1 to X3, Z, R1 to R4, and R1 to R4 are as defined in the chemical formula 1.

4. The polycyclic compound according to claim 1, wherein the chemical formula 1 is any one of the following chemical formulas 301 to 304:

[ chemical formula 301]

[ chemical formula 302]

[ chemical formula 303]

[ chemical formula 304]

In the chemical formulas 301 to 304 described above,

y1 is O, S, NR, CR22R23 or SiR22R23,

y1 is either 0 or 1 and,

r14 to R20 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted ring,

x1 to X3, R1 to R4, and R1 to R4 are as defined in the chemical formula 1.

5. The polycyclic compound according to claim 1, wherein Cy1 is one selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring, and a substituted or unsubstituted aliphatic heterocyclic ring, or a ring formed by fusing 2 or more rings selected from the group,

Z is O, S or NR11, and the catalyst is,

the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, halogen group, cyano group, alkyl group, cycloalkyl group, alkoxy group, aryloxy group, amino group, aryl group, condensed ring group of aromatic hydrocarbon ring and aliphatic hydrocarbon ring, and heterocyclic group, or with a substituent formed by joining 2 or more groups of the substituents, or without any substituent,

6. The polycyclic compound according to claim 1, wherein the chemical formula 1 is one selected from the group consisting of:

/>

7. an organic light emitting device comprising: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the polycyclic compound according to any one of claims 1 to 6.

8. The organic light-emitting device of claim 7, wherein the organic layer comprises a light-emitting layer,

the light-emitting layer includes the polycyclic compound.

9. The organic light-emitting device of claim 7, wherein the organic layer comprises a light-emitting layer,

the light emitting layer includes the polycyclic compound as a dopant of the light emitting layer, and includes a compound of the following chemical formula H as a host of the light emitting layer:

[ chemical formula H ]

In the chemical formula H described above, the amino acid sequence,

10. The organic light-emitting device according to claim 7, wherein the organic layer further comprises one or more layers selected from a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.