CN113841262A

CN113841262A - Organic light emitting device

Info

Publication number: CN113841262A
Application number: CN202180003325.3A
Authority: CN
Inventors: 李禹哲; 崔地宁; 金埙埈; 洪玩杓; 金周湖; 李豪中
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2020-01-20
Filing date: 2021-01-20
Publication date: 2021-12-24
Also published as: KR20230074687A; WO2021150092A1; KR20210093792A

Abstract

The present specification provides a compound of chemical formula 1 and an organic light emitting device including the same.

Description

Organic light emitting device

Technical Field

This specification claims priority to korean patent application No. 10-2020-.

The present description relates to organic light emitting devices.

Background

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

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

(patent document 1) Korean patent laid-open publication No. 2016-132822

Disclosure of Invention

Technical subject

The present specification provides an organic light emitting device.

Means for solving the problems

The present specification provides an organic light emitting device, comprising: an anode; a cathode; and an organic layer including a light-emitting layer between the anode and the cathode, wherein the light-emitting layer includes a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula a.

[ chemical formula 1]

In the above-described chemical formula 1,

y101 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, Y102 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group,

l1 and L2, which are identical to or different from one another, are each independently a direct bond or a substituted or unsubstituted arylene group,

cy1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

d is the deuterium, and the nitrogen is the hydrogen,

a is an integer of 0 to 4, when a is 2 or more, 2 or more Y101 s are the same as or different from each other,

b is an integer of 0 to 7, z is an integer of 1 to 8, b + z is an integer of 1 to 8,

when b is 2 or more, 2 or more Y102 s may be the same or different from each other,

adjacent 2 of the groups are bonded to the following chemical formula 2, and the others are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or bonded to L1,

[ chemical formula 2]

In the above-described chemical formula 2,

w is O, S, NR or CR' R ".

R, R ', R' and Y103, equal to or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

c is an integer of 0 to 4,

when c is 2 or more, 2 or more Y103 s may be the same or different from each other,

is a position bonded to the above chemical formula 1,

[ chemical formula A ]

In the above-mentioned chemical formula a,

a1 to A3, which are the same or different from each other, are each independently a monocyclic to polycyclic aromatic hydrocarbon ring or a monocyclic to polycyclic aromatic heterocycle,

r1 to R5 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, or a substituted or unsubstituted amine group, or combines with adjacent substituents to form a substituted or unsubstituted ring,

r1 and r2 are integers of 1 to 4, r3 is an integer of 1 to 3, and r1 to r3 are 2 or more, the substituents in parentheses are the same or different from each other.

Effects of the invention

The organic light emitting device described in this specification can improve electron injection and migration of the device by including chemical formula 1 and chemical formula a in the light emitting layer, and thus can obtain an organic light emitting device having excellent light emitting efficiency, low driving voltage, high efficiency, and long life.

Drawings

Fig. 1 to 3 illustrate an organic light emitting device according to an embodiment of the present specification.

1: substrate

2: anode

3: luminescent layer

4: cathode electrode

5: hole injection layer

6: hole transport layer

7: luminescent layer

8: electron transport layer

9: electron injection layer

Detailed Description

The present specification will be described in more detail below.

The present specification provides an organic light emitting device including the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula a in a light emitting layer. According to one example, the compound represented by the above chemical formula 1 is contained as a host of the light emitting layer, and the compound represented by the above chemical formula a is contained as a dopant of the light emitting layer.

The compound represented by the above chemical formula 1 increases dipole moment (dipole moment) of the molecule by including the substituent of chemical formula 2 having an additional heteroaromatic moiety fused to the dibenzofuran, and mobility of electrons and ability to inject electrons from the electrode are improved.

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

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

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

In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group (-CN), a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a silyl group, a boryl group, an alkoxy group, an alkyl group, a cycloalkyl group, an aryl group, and a heterocyclic group, or a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.

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

A substituent of (1).

In the present specification, the connection of 3 substituents includes not only the connection of (substituent 1) - (substituent 2) - (substituent 3) continuously but also the connection of (substituent 2) and (substituent 3) in (substituent 1). For example, 2 phenyl groups may be

A substituent of (1). The same explanation as above applies to the case where 4 or more substituents are bonded.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples thereof include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, and 1-methylhexyl.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 30. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, etc., but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, and more preferably a cycloalkyl group having 3 to 20 carbon atoms. Cycloalkyl groups include not only monocyclic groups but also bicyclic groups such as bridged rings (bridged rings), fused rings (fused rings), spiro rings (spiro rings). Specifically, there are mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl (adamantyl group), and the like.

In the present specification, the cycloalkenyl group is not particularly limited, but is preferably a cycloalkenyl group having 3 to 30 carbon atoms, and more preferably a cycloalkenyl group having 4 to 20 carbon atoms. Cycloalkenyl groups include not only monocyclic groups but also bicyclic groups such as bridgeheads, fused rings, spiro rings, and the like. Specifically, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclooctenyl and the like are exemplified, but not limited thereto.

In the present specification, the amine group may be selected from-NH₂Alkylamino, N-The number of carbon atoms of the alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino and heteroarylamino group is not particularly limited, but is preferably 0 to 30. Specific examples of the amine group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methylanthrylamino group, a diphenylamino group, an N-phenylnaphthylamino group, a ditolylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrylamino group, an N-phenylfluorenylamino group, an N-phenylterphenylamino group, an N-phenanthrenylfluorenylamino group, and an N-biphenylfluorenylamino group.

In the present specification, an N-alkylarylamino group means an amino group substituted with an alkyl group and an aryl group on the N of the amino group.

In this specification, an N-arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group on the N of the amine group.

In the present specification, an N-alkylheteroarylamine 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, the alkyl group in the alkylamino group, N-arylalkylamino group, and N-alkylheteroarylamino group is the same as that exemplified above for the alkyl group.

In the present specification, as examples of the heteroarylamino group, there are a substituted or unsubstituted monoheteroarylamino group, or a substituted or unsubstituted diheteroarylamino group. Heteroarylamine groups comprising more than 2 of the above-described heteroaryls may comprise a monocyclic heteroaryl, a polycyclic heteroaryl, or may comprise both a monocyclic heteroaryl and a polycyclic heteroaryl. For example, the heteroaryl group in the heteroarylamino group may be selected from the heteroaryl groups described below.

In this specification, examples of the heteroaryl group in the N-arylheteroarylamino group and the N-alkylheteroarylamino group are the same as those of the heteroaryl group described later.

In the present specification, the silyl group may be an alkylsilyl group or an arylsilyl group, and may also be a trialkylsilyl group or a triarylsilyl group. The number of carbon atoms of the silyl group is not particularly limited, but is preferably 1 to 30, the number of carbon atoms of the alkylsilyl group is 1 to 30, and the number of carbon atoms of the arylsilyl group may be 5 to 30. Specific examples thereof include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like.

In the present specification, the boron group may be-BR 100R101, and the above R100 and R101 may be the same or different and may each be independently selected from hydrogen, deuterium, halogen, a nitrile group, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In the present specification, the aryl group is not particularly limited, but an aryl group having 6 to 60 carbon atoms is preferable, and for example, an aryl group having 6 to 30 carbon atoms is preferable, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 60. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 60. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a phenalenyl group, a perylenyl group, a perylene group, a light-emitting element, and the like,

Examples of the group include a fluorenyl group and a fluoranthenyl group.

In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

In the case where the above-mentioned fluorenyl group is substituted, it may be

And the like. But is not limited thereto.

The above arylene group may be referred to the description of the above aryl group, except that it has a valence of 2.

In the present specification, the heterocyclic group contains 1 or more non-carbon atoms, i.e., hetero elements, and specifically, the above hetero elements may contain 1 or more atoms selected from O, N, S, Si, P and the like. The number of carbon atoms is not particularly limited, but is preferably 1 to 60, more preferably 2 to 60, and the heterocyclic group may be monocyclic or polycyclic. The heterocyclic group may be an aromatic ring, an aliphatic ring or a condensed ring thereof. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl, and the like,

Azolyl group,

Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl

Examples of the heterocyclic group include, but are not limited to, an azole group, a thiadiazole group, a phenothiazine group, and a dibenzofuran group.

The heteroaryl group means an aromatic heterocyclic group having a valence of 1, and the heteroarylene group means an aromatic heterocyclic group having a valence of 2. The above-mentioned heteroaryl and heteroarylene groups may be referred to the description of the above-mentioned heterocyclic groups, in addition to being aromatic.

In the present specification, the aryloxy group is a group having an aryl group bonded to an oxygen atom, and the aryl group of the aryloxy group is exemplified in the same manner as the above-mentioned aryl group. Concretely, the aryloxy group includes phenoxy, p-tolyloxy, m-tolyloxy, 3, 5-dimethyl-phenoxy, 2,4, 6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthracenyloxy, 2-anthracenyloxy, 9-anthracenyloxy, 1-phenanthrenyloxy, 3-phenanthrenyloxy, 9-phenanthrenyloxy and the like, and the arylthio group is an arylthio group

Examples of the mercapto group include, but are not limited to, phenylmercapto (Phenyl thio), 2-methylphenylthio, and 4-tert-butylphenylthio.

In the present specification, arylthio group

The above-mentioned description of the aryloxy group can be applied to a group having an aryl group bonded to a sulfur atom, except that the sulfur atom is used in place of the oxygen atom.

In the present specification, arylalkyl means an alkyl group to which an aryl group is bonded, and the above description about the aryl group and the alkyl group can be applied.

In the present specification, "energy level" refers to the magnitude of energy. Therefore, even when the energy level is expressed in the negative (-) direction from the vacuum level, the energy level is interpreted as referring to the absolute value of the energy value. For example, the HOMO (highest occupied molecular orbital) level refers to the distance from the vacuum level to the highest occupied molecular orbital. In addition, the LUMO (lowest unoccupied molecular orbital) level refers to the distance from the vacuum level to the lowest unoccupied molecular orbital.

In the present specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent closest in steric structure to the substituent, or another substituent substituted on an atom substituted with the substituent. For example, in a benzene ring, 2 substituents substituted at the ortho (ortho) position and 2 substituents substituted on the same carbon of an aliphatic ring may be interpreted as groups "adjacent" to each other.

In the present specification, in the substituted or unsubstituted ring formed by bonding to each other, "ring" means a hydrocarbon ring or a heterocyclic ring. The hydrocarbon ring may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic. The heterocyclic group may be substituted with the heterocyclic group described above except that the heterocyclic group has a valence of 2.

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

In the present specification, the aliphatic hydrocarbon ring means all hydrocarbon rings except for the aromatic hydrocarbon ring, and may include a cycloalkane ring, a cycloalkene ring. The description above for the cycloalkyl group can be applied to the cycloalkane ring other than the 2-valent group, and the description above for the cycloalkenyl group can be applied to the cycloalkene ring other than the 2-valent group. In addition, the substituted aliphatic hydrocarbon ring also includes an aromatic ring fused to the aliphatic hydrocarbon ring.

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

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

Next, chemical formula 1 will be described.

In the above chemical formula 1, the term "substituted or unsubstituted" means substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group, and an aryl group.

According to an embodiment of the present disclosure, adjacent 2 of chemical formula 1 are combined with chemical formula 2 below. Specifically, adjacent 2 of chemical formula 1 are bonded to 2 of chemical formula 2, and the bonding direction is not limited.

[ chemical formula 2]

In the above-described chemical formula 2,

w is O, S, NR or CR' R ",

c is an integer of 0 to 4,

is a position bound to the above chemical formula 1.

In one embodiment of the present specification, adjacent 2 of chemical formula 1 are bound to chemical formula 2, and the others, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are bound to L1.

In another embodiment, adjacent 2 of chemical formula 1 are bound to chemical formula 2, and the others are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or bound to L1.

In another embodiment, adjacent 2 of chemical formula 1 are combined with chemical formula 2, and the rest are the same or different from each other, and each is independently hydrogen or deuterium, or combined with L1.

In another embodiment, adjacent 2 of chemical formula 1 are bonded to chemical formula 2, and the rest is hydrogen, or is bonded to L1.

In another embodiment, adjacent 2 of chemical formula 1 are bonded to chemical formula 2, and the rest is deuterium, or bonded to L1.

According to an embodiment of the present disclosure, adjacent 2 of chemical formula 1 are bonded to chemical formula 2, any one of the others is hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and the other one is bonded to L1.

In one embodiment of the present specification, X in the chemical formula 2 is O, S, NR or CR' R ".

According to another embodiment, X is O.

According to another embodiment, X is S.

According to another embodiment, X is NR.

According to another embodiment, X is CR' R ".

According to an embodiment of the present specification, R, R', R ", and Y103 of chemical formula 2 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another embodiment, R, R', R ", and Y103, which may be the same or different from each other, are each independently hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium.

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

According to another embodiment, the above R is substituted or unsubstituted phenyl.

In another embodiment, the above R is phenyl substituted or unsubstituted with deuterium.

In another embodiment, R is phenyl.

According to an embodiment of the present specification, R' and R ″ are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, the above R 'and R' are the same or different from each other and are each independently methyl or phenyl.

In another embodiment, each of the above R 'and R' is methyl.

According to another embodiment, each of the above R 'and R' is phenyl.

In one embodiment of the present specification, Y103 is hydrogen or deuterium.

According to an embodiment of the present specification, when c of chemical formula 2 is an integer of 0 to 4 and c is 2 or more, 2 or more Y103 s are the same or different from each other.

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

[ chemical formula 1-1]

[ chemical formulas 1-2]

[ chemical formulas 1-3]

[ chemical formulas 1 to 4]

[ chemical formulas 1 to 5]

[ chemical formulas 1 to 6]

In the above chemical formulas 1-1 to 1-6,

l1, L2, Y101 to Y103, Cy1, W, D, z and a to c are as defined in

chemical formulae

1 and 2,

y104 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, d is an integer of 0 to 2,

when d is 2, 2Y 104 s are the same as or different from each other.

In one embodiment of the present specification, Y101 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, Y101 is hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium.

In another embodiment, Y101 is hydrogen or deuterium.

According to another embodiment, Y101 is hydrogen.

According to another embodiment, Y101 is deuterium.

According to an embodiment of the present disclosure, Y102 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

According to another embodiment, Y102 is hydrogen, deuterium, or an alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium.

According to another embodiment, Y102 is hydrogen or deuterium.

According to another embodiment, Y102 is hydrogen.

According to another embodiment, Y102 is deuterium.

According to an embodiment of the present specification, Y103 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

According to another embodiment, Y103 is hydrogen, deuterium, or an alkyl group of 1 to 30 carbon atoms substituted or unsubstituted with deuterium.

According to another embodiment, Y103 is hydrogen or deuterium.

According to another embodiment, Y103 is hydrogen.

According to another embodiment, Y103 is deuterium.

According to an embodiment of the present disclosure, Y104 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, Y104 is hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium.

In another embodiment, Y104 is hydrogen or deuterium.

According to another embodiment, Y104 is hydrogen.

According to another embodiment, Y104 is deuterium.

According to an embodiment of the present specification, when a is an integer of 0 to 4 and a is 2 or more, 2 or more Y101 s are the same or different from each other.

According to an embodiment of the present disclosure, when b is an integer of 0 to 7, z is an integer of 1 to 8, b + z is an integer of 1 to 8, and b is 2 or more, 2 or more Y102 s are the same as or different from each other.

According to an embodiment of the present disclosure, when d is an integer of 0 to 2 and d is 2, 2Y 104 s are the same or different from each other.

In one embodiment of the present specification, Cy1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms and containing 1 or more O as a hetero element.

According to another embodiment, the above Cy1 is an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium, or a heterocyclic ring having 2 to 60 carbon atoms containing 1 or more O as a hetero element substituted or unsubstituted with deuterium.

According to another embodiment, the above Cy1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

According to another embodiment, the above Cy1 is a phenyl group substituted or unsubstituted with deuterium, a naphthyl group substituted or unsubstituted with deuterium, a phenanthryl group substituted or unsubstituted with deuterium, a triphenyl group substituted or unsubstituted with deuterium, a pyrenyl group substituted or unsubstituted with deuterium, a dimethylfluorenyl group substituted or unsubstituted with deuterium, a diphenylfluorenyl group substituted or unsubstituted with deuterium, a dibenzofuranyl group substituted or unsubstituted with deuterium, a dibenzothiophenyl group substituted or unsubstituted with deuterium, or a phenylcarbazolyl group substituted or unsubstituted with deuterium.

According to an embodiment of the present disclosure, L1 and L2 are the same or different from each other and each independently represents a direct bond or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In one embodiment of the present specification, L1 and L2, which may be the same or different from each other, are each independently an arylene group having 6 to 60 carbon atoms, which is directly bonded to or substituted with deuterium.

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

In one embodiment of the present specification, L1 and L2, which may be the same or different from each other, are each independently an arylene group having 6 to 30 carbon atoms, which is directly bonded to or substituted with deuterium.

According to another embodiment, the above L1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

In another embodiment, L1 and L2, which are the same or different from each other, are each independently a direct bond, a phenylene group substituted or unsubstituted with deuterium, or a naphthylene group substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, the anthracene in the above chemical formula 1 is substituted with 1 or more deuterium.

According to another embodiment, anthracene and Cy1 in chemical formula 1 above are substituted with 1 or more deuterium.

According to another embodiment, the dibenzofuran condensed with chemical formula 2 and the anthracene of chemical formula 1 are respectively substituted with 1 or more deuterium.

According to another embodiment, the anthracene, dibenzofuran, and Cy1 condensed with chemical formula 2 in chemical formula 1 above are respectively substituted with 1 or more deuterium.

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

Among the above-mentioned compounds, the compounds of formula (I),

d is the deuterium, and the nitrogen is the hydrogen,

z is an integer of 1 to 8, z1 is an integer of 1 to 9, z2 to z5 are each an integer of 1 to 5, and z6 is an integer of 1 to 7.

The following description relates to chemical formula a.

An organic light emitting device according to an embodiment of the present specification includes a compound represented by the following chemical formula a in a light emitting layer.

[ chemical formula A ]

In the above-mentioned chemical formula a,

In one embodiment of the present specification, when R1 is 2 or more, a plurality of R1 s are the same as or different from each other. In another embodiment, when R2 is 2 or more, the plurality of R2 are the same as or different from each other. In another embodiment, when R3 is 2 or more, the plurality of R3 are the same as or different from each other.

In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted trialkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted triarylsilyl group having 6 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 10 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having a structure of hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 2 to 30 carbon atoms, or unsubstituted aryl group, or a substituted or unsubstituted aryl group having 2 carbon atoms, or unsubstituted alkoxy group, or a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, or a substituted or an aryl group, or unsubstituted alkoxy group, or a substituted or an aryl group having a substituted or an aryl group, or an aryl group having a substituted or unsubstituted aryl group having 2 carbon atom group, or a substituted or an aryl group, or a substituted group, or an aryl group having a substituted or a substituted group having a substituted or an aryl group, or a substituted or unsubstituted aryl group, or an aryl group having a substituted or an aryl group, or an aryl group having a substituted or unsubstituted aryl group having a group, or a group having a group, or a group having a group, or a group having a group, or a group having a, Or a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms, or a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, which is formed by bonding adjacent substituents to each other.

The above-mentioned R1 to R3 and the adjacent substituents are bonded to each other means that 2 of adjacent R1, 2 of adjacent R2, or 2 of adjacent R3 are bonded to each other.

In one embodiment of the present specification, R4 and R5, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, to which an aliphatic hydrocarbon ring is fused or unfused, or combine with an adjacent substituent to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R4 and R5, which are the same as or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms to which an aliphatic hydrocarbon ring having 5 to 30 carbon atoms is fused or unfused, or combine with an adjacent substituent to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

In one embodiment of the present specification, R4 and R5, which are the same as or different from each other, are each independently a 6 to 20 carbon atom-substituted or unsubstituted aryl group, which is a condensed or unfused aliphatic hydrocarbon ring having 6 to 30 carbon atoms, and which is substituted or unsubstituted with a1 to 6 carbon atom-containing alkyl group or a 6 to 60 carbon atom-containing arylalkyl group, or are combined with an adjacent substituent to form a2 to 30 carbon atom-substituted or unsubstituted ring having a1 to 6 carbon atom-containing alkyl group or a 6 to 30 carbon atom-containing aryl group.

In one embodiment of the present specification, R4 is a 6 to 20 carbon atom-containing aryl group which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an arylalkyl group having 6 to 60 carbon atoms and to which an aliphatic hydrocarbon ring having 6 to 30 carbon atoms is fused or not fused, or is combined with R1 to form an N-containing five-membered ring which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R5 is a 6 to 20 carbon atom-containing aryl group which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an arylalkyl group having 6 to 60 carbon atoms and to which an aliphatic hydrocarbon ring having 5 to 20 carbon atoms is fused or not fused, or is combined with R2 to form an N-containing five-membered ring which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 30 carbon atoms.

The above-mentioned N-containing five-membered ring means a ring in which the total number of carbons and N participating in ring formation is 5, including a case where an additional ring is fused on the formed ring. That is, when R4 is a substituted phenyl group and R1 is bonded to form a five-membered ring, the phenyl group of R4 is fused to the five-membered ring containing N,

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

[ chemical formula A-1]

In the above-mentioned chemical formula A-1,

r1 to R3 and R1 to R3 are as defined above for formula A,

r6 and R7 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, or a substituted or unsubstituted amine group, or combines with each other with adjacent substituents to form a substituted or unsubstituted ring,

r6 and r7 are integers of 0 to 5, and when r6 and r7 are 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted trialkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted triarylsilyl group having 6 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms, or are combined with adjacent substituents to each other to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

In one embodiment of the present specification, R1 to R3, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a trialkylsilyl group having 1 to 30 carbon atoms, a triarylsilyl group having 6 to 60 carbon atoms, an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, an N-containing aromatic heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms, an N-containing aliphatic heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms, or an arylamine group having 6 to 60 carbon atoms which is substituted or unsubstituted with a halogen group or an alkyl group having 1 to 10 carbon atoms, or combine with adjacent substituents to form an aliphatic hydrocarbon ring of 5 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group of 1 to 10 carbon atoms or an aryl group of 6 to 30 carbon atoms, an aliphatic heterocyclic ring of 2 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group of 1 to 10 carbon atoms or an aryl group of 6 to 30 carbon atoms, or an aromatic heterocyclic ring of 2 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group of 1 to 10 carbon atoms or an aryl group of 6 to 30 carbon atoms.

In one embodiment of the present specification, R1 to R3, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group of 1 to 6 carbon atoms which is substituted or unsubstituted with an aryl group of 6 to 20 carbon atoms, a cycloalkyl group of 3 to 20 carbon atoms, a trialkylsilyl group of 1 to 20 carbon atoms, a triarylsilyl group of 6 to 50 carbon atoms, an aryl group of 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group of 1 to 6 carbon atoms, an N-containing aromatic heterocyclic group of 2 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group of 1 to 6 carbon atoms or an aryl group of 6 to 20 carbon atoms, an N-containing heterocyclic group of 2 to 25 carbon atoms which is substituted or unsubstituted with an alkyl group of 1 to 6 carbon atoms or an aryl group of 6 to 20 carbon atoms, or an arylamine group of 6 to 40 carbon atoms which is substituted or unsubstituted with a halogen group or an alkyl group of 1 to 6 carbon atoms, or combine with each other with adjacent substituents to form an aliphatic hydrocarbon ring of 5 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group of 1 to 6 carbon atoms or an aryl group of 6 to 20 carbon atoms, an aliphatic heterocyclic ring of 2 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group of 1 to 6 carbon atoms or an aryl group of 6 to 20 carbon atoms, or an aromatic heterocyclic ring of 2 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group of 1 to 6 carbon atoms or an aryl group of 6 to 20 carbon atoms.

In one embodiment of the present specification, R1 and R2, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, a trialkylsilyl group having 1 to 20 carbon atoms, a triarylsilyl group having 6 to 50 carbon atoms, an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, an N-containing aromatic heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms, an N-containing aliphatic heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 40 carbon atoms which is substituted or unsubstituted with a halogen group, or combine with each other with adjacent substituents to form an aliphatic hydrocarbon ring of 5 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group of 1 to 6 carbon atoms or an aryl group of 6 to 20 carbon atoms, an aliphatic heterocyclic ring of 2 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group of 1 to 6 carbon atoms or an aryl group of 6 to 20 carbon atoms, or an aromatic heterocyclic ring of 2 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group of 1 to 6 carbon atoms or an aryl group of 6 to 20 carbon atoms.

In one embodiment of the present specification, R1 and R2, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, a trialkylsilyl group having 1 to 20 carbon atoms, a triarylsilyl group having 6 to 50 carbon atoms, an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, an N-containing aromatic heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, a group represented by the chemical formula 2-a described later, or an arylamine group having 6 to 40 carbon atoms which is substituted or unsubstituted with a halogen group, or may be bonded to an adjacent substituent to form a ring selected from the ring groups A described later.

In one embodiment of the present description, R3 is hydrogen; deuterium; an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 30 carbon atoms which is substituted or unsubstituted with deuterium; an N-containing aromatic heterocyclic group having 2 to 25 carbon atoms which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms which is substituted with deuterium; an N-containing aliphatic heterocyclic group having 2 to 25 carbon atoms which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms which is substituted with deuterium, an aryl group having 6 to 20 carbon atoms which is substituted with deuterium, or an aryl group having 6 to 20 carbon atoms which is substituted with deuterium; or an arylamine group having 6 to 40 carbon atoms which is substituted or unsubstituted with deuterium or an alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present description, R3 is hydrogen; deuterium; an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 20 carbon atoms which is substituted or unsubstituted with deuterium; an N-containing aromatic heterocyclic group having 2 to 25 carbon atoms which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms which is substituted with deuterium; a group represented by the following chemical formula 2-A; or an arylamine group having 6 to 40 carbon atoms which is substituted or unsubstituted with deuterium or an alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, R1 and R2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a methyl group, a tert-butyl group, an isopropyl group substituted or unsubstituted with a phenyl group, a cyclohexyl group substituted or unsubstituted with a methyl group, an adamantyl group, a trimethylsilyl group, a triphenylsilyl group, a phenyl group substituted or unsubstituted with a tert-butyl group, a carbazolyl group substituted or unsubstituted with a tert-butyl group, a hexahydrocarbazolyl group substituted or unsubstituted with a methyl group, a dihydroacridinyl group substituted or unsubstituted with a methyl group, an octahydroacridinyl group substituted or unsubstituted with a methyl group, a hexahydrodibenzoazasilyl group substituted or unsubstituted with a methyl group, or a diphenylamino group substituted or unsubstituted with a halogen group, or combine with an adjacent substituent to form a cyclohexene ring substituted or unsubstituted with a methyl group, a cyclopentene ring substituted or unsubstituted with a methyl group, A bicyclo [2.2.2] octene ring substituted or unsubstituted with a methyl group, a thiophene ring substituted or unsubstituted with a phenyl group substituted or unsubstituted with a (tert-butyl) dimethylphenyl group, a dihydrofuran ring substituted or unsubstituted with a methyl group, or a dihydrosilyl ring substituted or unsubstituted with a phenyl group.

The N-containing heterocyclic group of R1 to R3 may be a group represented by the following chemical formula 2-a.

In one embodiment of the present specification, R3, which are the same or different from each other, are each independently hydrogen, deuterium, a methyl group substituted or unsubstituted with deuterium, an adamantyl group, a carbazolyl group substituted or unsubstituted with deuterium or a tert-butyl group, a group represented by the following chemical formula 2-a, or a diphenylamino group substituted or unsubstituted with deuterium or a tert-butyl group.

In one embodiment of the present specification, R3, which are the same or different from each other, are each independently hydrogen; deuterium; methyl substituted or unsubstituted with deuterium; an adamantyl group; carbazolyl substituted or unsubstituted with deuterium or tert-butyl; hexahydrocarbazolyl substituted or unsubstituted with phenyl substituted with methyl, tert-butyl, phenyl or deuterium; a dihydroacridinyl group substituted or unsubstituted by methyl or tert-butyl; spiro [ acridine-fluorene ]; indenoindolyl substituted or unsubstituted with methyl; spiro [ dibenzosilyl-dibenzoazasilyl ]; a dihydrodibenzoazasilyl group substituted or unsubstituted with a phenyl group; indolyl substituted or unsubstituted with methyl; octahydroacridinyl substituted or unsubstituted by methyl; or a diphenylamino group substituted or unsubstituted with deuterium or a tert-butyl group.

When R1, R2, and R3 are bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring, a ring selected from the ring group a described later is specifically formed.

In one embodiment of the present specification, 2 of adjacent R1 or 2 of adjacent R2 are bonded to each other to form a ring selected from a cyclic group a described later.

According to an embodiment of the present specification, the chemical formula a-1 satisfies 1 or more of (1) to (3).

(1) At least one of R1 to R3, R6, and R7 is a substituted or unsubstituted cycloalkyl group, or a group represented by the following chemical formula 2-A

(2) At least one of R1 to R3, R6 and R7 is a group represented by the following chemical formula 2-B

(3) 2 of adjacent R1, 2 of adjacent R2, 2 of adjacent R3, 2 of adjacent R6, or 2 of adjacent R7 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, or a substituted or unsubstituted aromatic heterocyclic ring

In the above chemical formulas 2-A and 2-B,

t11 to T19 and Ar11 to Ar14 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, or a substituted or unsubstituted amine group, or combine with adjacent substituents to each other to form a substituted or unsubstituted ring,

l11 is a direct bond or a substituted or unsubstituted arylene group,

p1 is 0 or 1 and,

y1 is C or Si,

at least one of T17 to T19 is a substituted or unsubstituted aryl group,

refers to the position of binding to formula a-1.

In one embodiment of the present specification, R3 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted arylamine group, or a group represented by the above chemical formula 2-a.

In one embodiment of the present specification, at least one of R1, R2, R6, and R7 is a group represented by the above chemical formula 2-B.

In one embodiment of the present specification, 2 of adjacent R1, 2 of adjacent R2, 2 of adjacent R6, or 2 of adjacent R7 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, or a substituted or unsubstituted aromatic heterocyclic ring.

In one embodiment of the present specification, 2 of adjacent R1 or 2 of adjacent R2 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, or a substituted or unsubstituted aromatic heterocyclic ring.

In one embodiment of the present specification, 2 of adjacent R6 or 2 of adjacent R7 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, or a substituted or unsubstituted aromatic heterocyclic ring.

The "aliphatic hydrocarbon ring formed by bonding 2 of adjacent R1, 2 of adjacent R2, 2 of adjacent R3, 2 of adjacent R6, or 2 of adjacent R7" may be an aliphatic hydrocarbon ring having 5 to 20 carbon atoms. Specifically, a cyclohexene ring, a cyclopentene ring, a bicyclo [2.2.1] heptene ring or a bicyclo [2.2.2] octene ring, which rings are substituted with methyl or unsubstituted, may be mentioned.

Further, the "aromatic heterocyclic ring in which 2 of adjacent R1, 2 of adjacent R2, 2 of adjacent R3, 2 of adjacent R6, or 2 of adjacent R7 are bonded to each other" may be an aromatic heterocyclic ring having 5 to 20 carbon atoms including O, S, Si or N. Specifically, a thiophene ring, a dihydrofuran ring or a dihydrosilole ring, which is substituted or unsubstituted with a methyl group or a phenyl group, may be mentioned.

In one embodiment of the present specification, 2 of adjacent R1, 2 of adjacent R2, 2 of adjacent R3, 2 of adjacent R6, or 2 of adjacent R7 are bonded to each other to form an aliphatic hydrocarbon ring having 5 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms; an aliphatic heterocyclic ring having 2 to 20 carbon atoms and containing O, S, Si or N, which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms or an alkylaryl group having 6 to 30 carbon atoms; or an aromatic heterocyclic ring having 2 to 20 carbon atoms and containing O, S, Si or N, which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms or an alkylaryl group having 6 to 30 carbon atoms.

In an embodiment of the present specification, 2 of adjacent R1, 2 of adjacent R2, 2 of adjacent R3, 2 of adjacent R6, or 2 of adjacent R7 are combined with each other to form a cyclohexene ring substituted or unsubstituted with a methyl group, a cyclopentene ring substituted or unsubstituted with a methyl group, a bicyclo [2.2.2] octene ring substituted or unsubstituted with a methyl group, a thiophene ring substituted or unsubstituted with a phenyl group substituted or unsubstituted with a (tert-butyl) dimethylphenyl group, a dihydrofuran substituted or unsubstituted with a methyl group, or a dihydrosilole ring substituted or unsubstituted with a phenyl group.

In one embodiment of the present specification, 2 of adjacent R1 or 2 of adjacent R2 are bonded to each other to form an aliphatic hydrocarbon ring having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms; an aliphatic heterocyclic ring having 2 to 20 carbon atoms and containing O, S, Si or N, which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms or an alkylaryl group having 6 to 30 carbon atoms; or an aromatic heterocyclic ring having 2 to 20 carbon atoms and containing O, S, Si or N, which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms or an alkylaryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, 2 of adjacent R1 or 2 of adjacent R2 are combined with each other to form a cyclohexene ring substituted or unsubstituted by a methyl group, a cyclopentene ring substituted or unsubstituted by a methyl group, a bicyclo [2.2.2] octene ring substituted or unsubstituted by a methyl group, a thiophene ring substituted or unsubstituted by a phenyl group substituted or unsubstituted by a (tert-butyl) dimethylphenyl group, a dihydrofuran substituted or unsubstituted by a methyl group, or a dihydrosilole ring substituted or unsubstituted by a phenyl group.

In one embodiment of the present specification, 2 of adjacent R6 or 2 of adjacent R7 are bonded to each other to form a cyclohexene ring substituted or unsubstituted by a methyl group, and a cyclopentene ring substituted or unsubstituted by a methyl group.

In one embodiment of the present specification, L11 is a direct bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L11 is a direct bond or phenylene.

In one embodiment of the present description, L11 is a direct bond.

In one embodiment of the present specification, T11 to T14, equal to or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, T11 to T14 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, T11 to T14 are the same or different from each other and are each independently hydrogen, deuterium, tert-butyl or phenyl.

In one embodiment of the present specification, T15 and T16, which are the same or different from each other, are each independently hydrogen, deuterium, 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 hydrocarbon ring.

In one embodiment of the present specification, T15 and T16 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or are combined with each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 20 carbon atoms.

In one embodiment of the present specification, T15 and T16, which are the same or different from each other, are each independently hydrogen, deuterium, or methyl, or are combined with each other while being phenyl to form a fluorene ring.

In one embodiment of the present specification, Y1 is C.

In one embodiment of the present specification, Y1 is Si.

In one embodiment of the present specification, 2 of Ar11 to Ar14 are bonded to each other to form a cyclopentane ring, a cyclohexane ring, or a cycloheptane ring, and the remaining 2 are hydrogen, deuterium, or methyl.

In one embodiment of the present specification, 2 of Ar11 to Ar14 are bonded to each other to form a cyclohexane ring, and the remaining 2 are hydrogen, deuterium, or methyl.

In one embodiment of the present specification, Ar11 to Ar14 combine with each other to form a substituted or unsubstituted aromatic ring.

In one embodiment of the present specification, Ar11 to Ar14 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 20 carbon atoms.

In one embodiment of the present specification, Ar11 to Ar14 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, or an aromatic heterocyclic ring having 2 to 20 carbon atoms.

In one embodiment of the present specification, Ar11 to Ar14 combine with each other to form a benzene ring, an indene ring substituted or unsubstituted with a methyl group, a benzofuran ring, or a benzothiophene ring.

In one embodiment of the present specification, i) p is 1, and Ar11 to Ar14 are bonded to each other to form a substituted or unsubstituted monocyclic aromatic hydrocarbon ring, or ii) p is 0, and Ar11 to Ar14 are bonded to each other to form a substituted or unsubstituted bicyclic aromatic ring containing a five-membered ring.

In one embodiment of the present specification, i) p is 1, and Ar11 to Ar14 are bonded to each other to form a monocyclic aromatic hydrocarbon ring, or ii) p is 0, and Ar11 to Ar14 are bonded to each other to form a bicyclic aromatic hydrocarbon ring containing a five-membered ring or a bicyclic aromatic heterocycle containing a five-membered ring, which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, i) p is 1 and Ar11 to Ar14 are bonded to each other to form a benzene ring, or ii) p is 0 and Ar11 to Ar14 are bonded to each other to form an indene ring, a benzofuran ring, or a benzothiophene ring, which are substituted or unsubstituted with a methyl group.

In one embodiment of the present specification, the chemical formula 2-a is represented by any one of the following chemical formulae 2-a-1 to 2-a-5.

In the above chemical formulas 2-A-1 to 2-A-5,

l11, T11 to T16, Y1 and p1 are as defined in chemical formula 2-A,

y6 is O, S, C (T26) (T27) or Si (T26) (T27),

t20 to T29, which are identical to or different from one another, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

cy5 is an aliphatic hydrocarbon ring,

cy6 is an aromatic hydrocarbon ring,

when t28 and t29 are integers of 0 to 10 and t28 and t29 are each 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, Y6 is O or S.

In one embodiment of the present specification, Y6 is C (T26) (T27) or Si (T26) (T27).

In one embodiment of the present specification, Y6 is C (T26) (T27).

In one embodiment of the present specification, Y6 in the above chemical formula 2-A-5 is C (T26) (T27).

In one embodiment of the present disclosure, when T28 is an integer of 0 to 6 and T28 is 2 or more, the plurality of T28 are the same as or different from each other.

In one embodiment of the present disclosure, when T29 is an integer of 0 to 10 and T29 is 2 or more, the plurality of T29 are the same as or different from each other.

In one embodiment of the present specification, T20 to T27 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, T20 to T27 are the same as or different from each other, and each independently hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, T20 to T27 are the same or different from each other, and are each independently hydrogen, deuterium, or methyl.

In one embodiment of the present specification, T20 to T27 are each methyl.

In one embodiment of the present specification, T28 and T29 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, T28 and T29, which are the same or different from each other, are each independently hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, T28 and T29, equal to or different from each other, are each independently hydrogen, deuterium, tert-butyl or phenyl.

In one embodiment of the present specification, T28 and T29, equal to or different from each other, are each independently hydrogen, deuterium, or tert-butyl.

In one embodiment of the present specification, T28 is hydrogen, deuterium, tert-butyl or phenyl.

In one embodiment of the present description, T28 is hydrogen, deuterium, or tert-butyl.

In one embodiment of the present specification, T28 is hydrogen or deuterium.

In one embodiment of the present specification, T29 is hydrogen or deuterium.

In one embodiment of the present specification, Cy5 is an aliphatic hydrocarbon ring having 5 to 20 carbon atoms.

In one embodiment of the present description, Cy5 is a cyclopentane, cyclohexane or cycloheptane ring.

In one embodiment of the present specification, Cy5 is a cyclohexane ring.

In one embodiment of the present specification, Cy6 is an aromatic hydrocarbon ring having 5 to 20 carbon atoms.

In one embodiment of the present specification, Cy6 is a benzene ring.

In one embodiment of the present specification, T17 to T19, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and at least one of T17 to T19 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, T17 to T19 are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and at least one of T17 to T19 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, T17 to T19, which are the same as or different from each other, are each independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, and at least one of T17 to T19 is an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.

In one embodiment of the present specification, T17 to T19, which are the same or different from each other, are each independently an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms, and at least one of T17 to T19 is an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, T17 to T19, which are the same as or different from each other, are each independently a methyl group substituted or unsubstituted with deuterium, or a phenyl group substituted or unsubstituted with deuterium, and at least one of T17 to T19 is a phenyl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, T17 to T19, equal to or different from each other, are each independently methyl or phenyl, and at least one of T17 to T19 is phenyl.

In one embodiment of the present specification, one of T17 to T19 is phenyl and the remaining 2 are methyl.

In one embodiment of the present specification, R6 and R7, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group, or combine with each other with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring.

In one embodiment of the present specification, R6 and R7, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with each other with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms.

In one embodiment of the present specification, R6 and R7, equal to or different from each other, are each independently hydrogen; deuterium; a halogen group; an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium, an aryl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms which is substituted with deuterium; a cycloalkyl group having 3 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms; or an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium, or an aliphatic hydrocarbon ring having 3 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, in combination with adjacent substituents.

In one embodiment of the present specification, R6 and R7, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a methyl group substituted or unsubstituted by deuterium, a tert-butyl group substituted or unsubstituted by deuterium, a cyclohexyl group substituted or unsubstituted by a methyl group, or a phenyl group, or 2 of adjacent R6 or 2 of adjacent R7 are combined with each other to form a cyclohexene ring substituted or unsubstituted by a methyl group, or a cyclopentene ring substituted or unsubstituted by a methyl group.

In one embodiment of the present specification, R6 and R7, equal to or different from each other, are each independently hydrogen; deuterium; a halogen group; an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium, an aryl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms which is substituted with deuterium; a cycloalkyl group having 3 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms; or an aryl group of 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

In one embodiment of the present specification, R6 and R7, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a methyl group substituted or unsubstituted with deuterium, a tert-butyl group substituted or unsubstituted with deuterium, a cyclohexyl group substituted or unsubstituted with methyl, or a phenyl group.

In one embodiment of the present specification, a ring in which 2 of adjacent R1, 2 of adjacent R2, 2 of adjacent R3, 2 of adjacent R6, or 2 of adjacent R7 are bonded to each other is one selected from the following ring groups a.

[ Cyclic group A ]

In the above-mentioned ring group A,

is carbon involved in ring formation in R1, R2 and R3,

y10 and Y11, equal to or different from each other, are each independently O, S, Si (Ra3) (Ra4), C (Ra3) (Ra4) or N (Ra5),

r41 to R43 and Ra3 to Ra5, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and combine with an adjacent substituent to form an aromatic ring or an aliphatic ring,

p6 is an integer of 1 to 3,

when r41 is an integer of 0 to 8, r42 is an integer of 0 to 4, r43 is an integer of 0 to 2, and r41 to r43 are each 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, when R41 is 2 or more, a plurality of R41 s are the same as or different from each other. In another embodiment, when R42 is 2 or more, the plurality of R42 are the same as or different from each other. In another embodiment, when R43 is 2, the plurality of R43 are the same as or different from each other.

In the above structure, is a position fused with the above chemical formula a-1.

In one embodiment of the present specification, p6 is 1 or 2.

In one embodiment of the present specification, R41 to R43 and Ra3 to Ra5, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R41 to R43 and Ra3 to Ra5 are the same or different from each other, and each independently represents hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, R41 to R43, which are the same or different from each other, are each independently hydrogen, deuterium, or methyl.

In one embodiment of the present specification, Ra3 to Ra5 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ra3 to Ra5 are the same as or different from each other, and each independently represents an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, Ra3 to Ra5 are each phenyl.

In one embodiment of the present specification, Y10 and Y11, which are the same or different from each other, are each independently O, S, N (Ra5) or Si (Ra3) (Ra 4).

In one embodiment of the present specification, a ring formed by bonding 2 of adjacent R1 or 2 of adjacent R2 to each other is one selected from the above ring groups a.

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

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

r1 to R3, R1 and R3 are as defined in formula A,

y2 to Y4, which are identical to or different from each other, are each independently C or Si,

ar21 to Ar32, R6, and Z1 to Z6 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, or a substituted or unsubstituted amine group, or combine with adjacent substituents to each other to form a substituted or unsubstituted ring,

p2 to p4 are each 0 or 1,

r6 is an integer of 0 to 5,

r1 'is an integer of 0 to 3, r2' is an integer of 0 to 3, and when r6, r1 'and r2' are each 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, when R1' is 2 or more, a plurality of R1 s may be the same or different from each other. In another embodiment, when R2' is 2 or more, the plurality of R2 are the same as or different from each other. In another embodiment, when R6 is 2 or more, the plurality of R6 are the same as or different from each other.

In one embodiment of the present specification, the above descriptions of R1 to R3 of the above formulas A-2 and A-3 can be applied to R1 to R3 of the above formula A-1.

In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently represents hydrogen, deuterium, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted trialkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms, or are combined with adjacent substituents to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms.

In one embodiment of the present specification, R1 to R3, which are the same or different from each other, are each independently hydrogen; deuterium; a cyano group; an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with deuterium, an aryl group having 6 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which is substituted with deuterium; a cycloalkyl group having 3 to 30 carbon atoms; a trialkylsilyl group having 1 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 carbon atoms which is substituted with deuterium; an N-containing aromatic heterocycle having 2 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; an N-containing aliphatic heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or an arylamine group of carbon number 6 to 60 which is substituted or unsubstituted with deuterium or an alkyl group of carbon number 1 to 10, or an aliphatic hydrocarbon ring of carbon number 6 to 30 which is substituted or unsubstituted with deuterium or an alkyl group of carbon number 1 to 10, is bonded to each other with an adjacent substituent.

In one embodiment of the present specification, R1 to R3, which are the same or different from each other, are each independently hydrogen; deuterium; a cyano group; an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium, an aryl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms which is substituted with deuterium; a cycloalkyl group having 3 to 20 carbon atoms; a trialkylsilyl group having 1 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms which is substituted with deuterium; an N-containing aromatic heterocyclic group having 2 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms; an N-containing aliphatic heterocyclic group having 2 to 25 carbon atoms which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; or an arylamine group of carbon number 6 to 40 which is substituted or unsubstituted with deuterium or an alkyl group of carbon number 1 to 6, or an aliphatic hydrocarbon ring of carbon number 5 to 20 which is substituted or unsubstituted with deuterium or an alkyl group of carbon number 1 to 6, is bonded to each other with an adjacent substituent.

In one embodiment of the present specification, R1 to R3, which are the same or different from each other, are each independently hydrogen; deuterium; a cyano group; an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium, an aryl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms which is substituted with deuterium; a cycloalkyl group having 3 to 20 carbon atoms; a trialkylsilyl group having 1 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms which is substituted with deuterium; a group represented by the above chemical formula 2-A; or an arylamine group of carbon number 6 to 40 which is substituted or unsubstituted with deuterium or an alkyl group of carbon number 1 to 6, or an aliphatic hydrocarbon ring of carbon number 5 to 20 which is substituted or unsubstituted with deuterium or an alkyl group of carbon number 1 to 6, is bonded to each other with an adjacent substituent.

In one embodiment of the present specification, R1 and R2, equal to or different from each other, are each independently hydrogen; deuterium; a cyano group; an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium, an aryl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms which is substituted with deuterium; a trialkylsilyl group having 1 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 10 carbon atoms which is substituted with deuterium; an N-containing aliphatic heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; an N-containing aromatic heterocyclic group having 2 to 20 carbon atoms; an N-containing aliphatic heterocyclic group having 2 to 25 carbon atoms which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; or an arylamine group having 6 to 40 carbon atoms, or an aliphatic hydrocarbon ring having 5 to 20 carbon atoms which is unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms and is bonded to an adjacent substituent.

In one embodiment of the present specification, R1 and R2, equal to or different from each other, are each independently hydrogen; deuterium; a cyano group; an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium, an aryl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms which is substituted with deuterium; a trialkylsilyl group having 1 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 10 carbon atoms which is substituted with deuterium; a carbazolyl group; a group represented by the above chemical formula 2-A-1; a group represented by the above chemical formula 2-A-2; a group represented by the above chemical formula 2-A-3; a group represented by the above chemical formula 2-A-4; or an arylamine group having 6 to 40 carbon atoms, or an aliphatic hydrocarbon ring having 5 to 20 carbon atoms which is substituted or unsubstituted with deuterium or an alkyl group having 1 to 6 carbon atoms and is combined with an adjacent substituent.

In one embodiment of the present description, R3 is hydrogen; deuterium; an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 20 carbon atoms; an arylamine group having 6 to 40 carbon atoms which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms which is substituted with deuterium; or a N-containing heterocyclic group having 2 to 25 carbon atoms which is unsubstituted or substituted with deuterium, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R1 and R2, equal to or different from each other, are each independently hydrogen; deuterium; a cyano group; methyl substituted or unsubstituted with deuterium; a tertiary butyl group; isopropyl substituted or unsubstituted with deuterium, phenyl, or phenyl substituted with deuterium; a trimethylsilyl group; phenyl substituted or unsubstituted with deuterium, a halogen group, or tert-butyl; a carbazolyl group; hexahydrocarbazolyl substituted or unsubstituted with methyl; spiro [ acridine-fluorene ]; a dihydroacridinyl group substituted or unsubstituted with a methyl group; or a diphenylamino group, or combine with each other with adjacent substituents to form a cyclohexene ring substituted or unsubstituted with a methyl group.

In one embodiment of the present description, R3 is hydrogen; deuterium; methyl substituted or unsubstituted with deuterium; a tertiary butyl group; an adamantyl group; a diphenylamino group substituted or unsubstituted with deuterium, tert-butyl; a group represented by the above chemical formula 2-A-1; a group represented by the above chemical formula 2-A-2; a group represented by the above chemical formula 2-A-3; or a group represented by the above chemical formula 2-A-4.

In one embodiment of the present specification, R6 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or combines with each other with adjacent substituents to form a substituted or unsubstituted hydrocarbon ring.

In one embodiment of the present specification, R6 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or is combined with adjacent R6 to form a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms.

In one embodiment of the present description, R6 is hydrogen; deuterium; a halogen group; an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium, an aryl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms which is substituted with deuterium; or an aryl group of 6 to 30 carbon atoms substituted or unsubstituted with deuterium, or an aliphatic hydrocarbon ring of 3 to 20 carbon atoms formed by bonding adjacent R6 to each other.

In one embodiment of the present specification, R6, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a methyl group substituted or unsubstituted with deuterium, a tert-butyl group substituted or unsubstituted with deuterium, or a phenyl group substituted or unsubstituted with deuterium, or combine with each other with adjacent R6 to form a cyclohexene ring substituted or unsubstituted with methyl.

In one embodiment of the present specification, Z1 to Z6, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and combine with adjacent substituents to form a substituted or unsubstituted ring.

In one embodiment of the present specification, Z1 to Z6 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and adjacent substituents are bonded to each other to form a substituted or unsubstituted ring having 6 to 20 carbon atoms.

In one embodiment of the present specification, Z1 to Z6 are the same as or different from each other, and each independently hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, and combine with an adjacent substituent to form a tricyclic ring substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms substituted with deuterium.

The above-mentioned Z1 to Z6 and the adjacent substituent are bonded to each other means that Z1 and Z2, Z3 and Z4, or Z5 and Z6 are bonded to each other.

In one embodiment of the present specification, the ring formed by combining Z1 to Z6 and an adjacent substituent with each other is a fluorene ring or a xanthene ring. Specifically, 2 adjacent substituents are phenyl groups and directly bond to each other while forming a fluorene ring, or phenyl groups and form a xanthene ring by-O-bonding.

In one embodiment of the present specification, Z1 and Z2, which are the same or different from each other, are each independently a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group and are directly bonded to each other to form a substituted or unsubstituted fluorene ring, or a substituted or unsubstituted phenyl group and are bonded by — O "to form a substituted or unsubstituted xanthene ring.

In one embodiment of the present specification, Z3 and Z4, which are the same or different from each other, are each independently a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group and are directly bonded to each other to form a substituted or unsubstituted fluorene ring, or a substituted or unsubstituted phenyl group and are bonded by — O "to form a substituted or unsubstituted xanthene ring.

In one embodiment of the present specification, Z5 and Z6, which are the same or different from each other, are each independently a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group and are directly bonded to each other to form a substituted or unsubstituted fluorene ring, or a substituted or unsubstituted phenyl group and are bonded by — O "to form a substituted or unsubstituted xanthene ring.

In one embodiment of the present specification, Z1 and Z2, equal to or different from each other, are each independently methyl substituted or unsubstituted with deuterium; or phenyl substituted or unsubstituted with deuterium, tert-butyl or tert-butyl substituted with deuterium and bonded directly to each other to form a fluorene ring substituted or unsubstituted with deuterium, tert-butyl or tert-butyl substituted with deuterium; or is a tert-butylphenyl group substituted with deuterium, tert-butyl or with deuterium and forms a xanthene ring substituted or unsubstituted with deuterium, tert-butyl or with deuterium substituted tert-butyl by a-O-bond.

In one embodiment of the present specification, Z3 and Z4, equal to or different from each other, are each independently methyl substituted or unsubstituted with deuterium; or phenyl substituted or unsubstituted with deuterium, tert-butyl or tert-butyl substituted with deuterium and bonded directly to each other to form a fluorene ring substituted or unsubstituted with deuterium, tert-butyl or tert-butyl substituted with deuterium; or is a tert-butylphenyl group substituted with deuterium, tert-butyl or with deuterium and forms a xanthene ring substituted or unsubstituted with deuterium, tert-butyl or with deuterium substituted tert-butyl by a-O-bond.

In one embodiment of the present specification, Z5 and Z6, equal to or different from each other, are each independently methyl substituted or unsubstituted with deuterium; or phenyl substituted or unsubstituted with deuterium, tert-butyl or tert-butyl substituted with deuterium and bonded directly to each other to form a fluorene ring substituted or unsubstituted with deuterium, tert-butyl or tert-butyl substituted with deuterium; or is a tert-butylphenyl group substituted with deuterium, tert-butyl or with deuterium and forms a xanthene ring substituted or unsubstituted with deuterium, tert-butyl or with deuterium substituted tert-butyl by a-O-bond.

In one embodiment of the present specification, Ar21 to Ar32, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or combine with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring.

In one embodiment of the present specification, Ar21 to Ar32 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or an aromatic hydrocarbon ring having 6 to 10 carbon atoms and having 5 to 20 carbon atoms in combination with an adjacent substituent to form a substituted or unsubstituted aliphatic hydrocarbon ring having 6 to 10 carbon atoms.

In one embodiment of the present specification, Ar21 to Ar32 are the same as or different from each other, and each independently represents an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or forms an aliphatic or aromatic hydrocarbon ring having 6 to 10 carbon atoms which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms substituted with deuterium, or an aromatic hydrocarbon ring having 5 to 20 carbon atoms and is bonded to an adjacent substituent.

The formation of a ring by bonding Ar21 to Ar32 and adjacent substituents to each other means that 2 of Ar21 to Ar24 are bonded to form an aliphatic hydrocarbon ring, 2 of Ar25 to Ar28 are bonded to form an aliphatic hydrocarbon ring, 2 of Ar29 to Ar32 are bonded to form an aliphatic hydrocarbon ring, Ar21 to Ar24 are bonded to each other to form an aromatic hydrocarbon ring, Ar25 to Ar28 are bonded to each other to form an aromatic hydrocarbon ring, or Ar29 to Ar32 are bonded to each other to form an aromatic hydrocarbon ring.

In one embodiment of the present specification, i) 2 of Ar21 to Ar24 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 10 carbon atoms, and the remaining 2 are hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or ii) Ar21 to Ar24 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 10 carbon atoms.

In one embodiment of the present specification, i) 2 of Ar21 to Ar24 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 10 carbon atoms, and the remaining 2 are hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, or ii) Ar21 to Ar24 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 10 carbon atoms which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms which is substituted with deuterium.

In one embodiment of the present specification, i) 2 of Ar21 to Ar24 are bonded to each other to form a cyclohexane ring, and the remaining 2 are hydrogen, deuterium, a methyl group substituted or unsubstituted with deuterium, or a phenyl group substituted or unsubstituted with deuterium, or ii) Ar21 to Ar24 are bonded to each other to form a benzene ring substituted or unsubstituted with deuterium, a methyl group, a tert-butyl group, a methyl group substituted with deuterium, or a tert-butyl group substituted with deuterium; or an indene ring substituted or unsubstituted with methyl.

In one embodiment of the present specification, i) 2 of Ar25 to Ar28 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 10 carbon atoms, and the remaining 2 are hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or ii) Ar25 to Ar28 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 10 carbon atoms.

In one embodiment of the present specification, i) 2 of Ar25 to Ar28 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 10 carbon atoms, and the remaining 2 are hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, or ii) Ar25 to Ar28 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 10 carbon atoms which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms which is substituted with deuterium.

In one embodiment of the present specification, i) 2 of Ar25 to Ar28 are bonded to each other to form a cyclohexane ring, and the remaining 2 are hydrogen, deuterium, a methyl group substituted or unsubstituted with deuterium, or a phenyl group substituted or unsubstituted with deuterium, or ii) Ar25 to Ar28 are bonded to each other to form a benzene ring substituted or unsubstituted with deuterium, a methyl group, a tert-butyl group, a methyl group substituted with deuterium, or a tert-butyl group substituted with deuterium; or an indene ring substituted or unsubstituted with methyl.

In one embodiment of the present specification, i) 2 of Ar29 to Ar32 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 10 carbon atoms, and the remaining 2 are hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or ii) Ar29 to Ar32 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 10 carbon atoms.

In one embodiment of the present specification, i) 2 of Ar29 to Ar32 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 10 carbon atoms, and the remaining 2 are hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, or ii) Ar29 to Ar32 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 10 carbon atoms which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms which is substituted with deuterium.

In one embodiment of the present specification, i) 2 of Ar29 to Ar32 are bonded to each other to form a cyclohexane ring, and the remaining 2 are hydrogen, deuterium, a methyl group substituted or unsubstituted with deuterium, or a phenyl group substituted or unsubstituted with deuterium, or ii) Ar29 to Ar32 are bonded to each other to form a benzene ring substituted or unsubstituted with deuterium, a methyl group, a tert-butyl group, a methyl group substituted with deuterium, or a tert-butyl group substituted with deuterium; or an indene ring substituted or unsubstituted with methyl.

In one embodiment of the present specification, Y2 is C.

In one embodiment of the present specification, Y3 is C.

In one embodiment of the present specification, Y4 is C.

In one embodiment of the present specification, Y2 is Si.

In one embodiment of the present specification, Y3 is Si.

In one embodiment of the present specification, Y4 is Si.

In one embodiment of the present specification, at least one of a1 and a2 of the above chemical formula a is represented by the following chemical formula 2-C.

[ chemical formula 2-C ]

In the above chemical formula 2-C, X is a position fused to the chemical formula a, X is N (Ra1), O or S, Ra1 is a substituted or unsubstituted aryl group, and E1 is an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a fused ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

In one embodiment of the present specification, E1 is an aromatic hydrocarbon ring having 6 to 20 carbon atoms, an aliphatic hydrocarbon ring having 5 to 20 carbon atoms, or a condensed ring of an aromatic hydrocarbon ring having 6 to 20 carbon atoms and an aliphatic hydrocarbon ring having 5 to 20 carbon atoms.

In one embodiment of the present specification, E1 is a monocyclic to bicyclic aromatic hydrocarbon ring, a monocyclic to bicyclic aliphatic hydrocarbon ring, or a condensed ring of a monocyclic aromatic hydrocarbon ring and a monocyclic aliphatic hydrocarbon ring. In one embodiment of the present specification, E1 forms one ring selected from the group consisting of a benzene ring, a cyclopentene ring, a cyclohexene ring, a bicyclo [2.2.1] heptene ring, and a bicyclo [2.2.2] octene ring or 2 rings fused together selected from the group.

In one embodiment of the present specification, E1 is a benzene ring, a cyclopentene ring, a cyclohexene ring, a bicyclo [2.2.1] heptene ring, a bicyclo [2.2.2] octene ring, a tetrahydronaphthalene ring, an indane ring, a tetrahydromethylenenaphthalene ring or a tetrahydroethylenenaphthalene ring.

In one embodiment of the present specification, at least one of a1 and a2 in the chemical formula a is represented by the chemical formula 2-C, and the remainder is a benzene ring.

In one embodiment of the present specification, a1 is represented by the above chemical formula 2-C, and a2 is a benzene ring.

In one embodiment of the present specification, a1 is a benzene ring, and a2 is represented by the above chemical formula 2-C.

In one embodiment of the present specification, a1 and a2, which are the same as or different from each other, are each independently represented by the above chemical formula 2-C.

According to an embodiment of the present disclosure, the chemical formula a is represented by any one of the following chemical formulas a-4 to a-7.

[ chemical formula A-4]

[ chemical formula A-5]

[ chemical formula A-6]

[ chemical formula A-7]

In the above chemical formulae A-4 to A-7,

r1, R3 to R5, R1 and R3 are as defined in formula A,

e1 and E2, which may be the same or different from each other, are each independently an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,

x1 and X2, which are identical to or different from each other, are each independently N (Ra), O or S,

r1", R2" and Ra, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, or a substituted or unsubstituted amine group, or combine with adjacent substituents each other to form a substituted or unsubstituted ring,

when r1 'and r2' are integers of 0 or more and r1 'and r2' are each 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, when R1 "is 2 or more, a plurality of R1" are the same as or different from each other. In another embodiment, when R2 "is 2 or more, the plurality of R2" are the same as or different from each other.

In one embodiment of the present specification, E1 and E2 are the same as or different from each other, and each independently represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms, an aliphatic hydrocarbon ring having 5 to 20 carbon atoms, or a condensed ring of an aromatic hydrocarbon ring having 6 to 20 carbon atoms and an aliphatic hydrocarbon ring having 5 to 20 carbon atoms.

In one embodiment of the present specification, E1 and E2 are the same as or different from each other, and each independently represents a monocyclic to bicyclic aromatic hydrocarbon ring, a monocyclic to bicyclic aliphatic hydrocarbon ring, or a condensed ring of a monocyclic aromatic hydrocarbon ring and a monocyclic aliphatic hydrocarbon ring.

In one embodiment of the present specification, E1 and E2, which are the same as or different from each other, each independently form one ring selected from the group consisting of a benzene ring, a cyclopentene ring, a cyclohexene ring, a bicyclo [2.2.1] heptene ring, and a bicyclo [2.2.2] octene ring or 2 rings fused together selected from the above group.

In one embodiment of the present specification, E1 and E2, which are the same or different from each other, are each independently a benzene ring, a cyclopentene ring, a cyclohexene ring, a bicyclo [2.2.1] heptene ring, a bicyclo [2.2.2] octene ring, a tetrahydronaphthalene ring, an indane ring, a tetrahydromethylenenaphthalene ring, or a tetrahydroethylidenenaphthalene ring.

In one embodiment of the present specification, E1 and E2, which are the same or different from each other, are each independently a benzene ring, a cyclopentene ring or a cyclohexene ring.

In one embodiment of the present specification, Ra is substituted or unsubstituted aryl.

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

In one embodiment of the present specification, Ra is an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, Ra is phenyl substituted or unsubstituted with tert-butyl.

In one embodiment of the present specification, the above descriptions of R1, R3, R1 "and R2" of the above formulas A-4 to A-7 can be applied to the above descriptions of R1 to R3 of the formula A-1.

In one embodiment of the present specification, R1, R3, R1 "and R2" are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted trialkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms.

In one embodiment of the present specification, R1, R3, R1 "and R2" are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted trialkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted triarylsilyl group having 6 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms.

In one embodiment of the present specification, R3, R1 "and R2" are the same as or different from each other, and each is independently hydrogen, deuterium, an alkyl group of 1 to 10 carbon atoms substituted with an aryl group of 6 to 30 carbon atoms or unsubstituted, a trialkylsilyl group of 1 to 30 carbon atoms, a triarylsilyl group of 6 to 60 carbon atoms, an aryl group of 6 to 30 carbon atoms, an N-containing aliphatic heterocyclic group of 2 to 30 carbon atoms substituted with an alkyl group of 1 to 10 carbon atoms or an aryl group of 6 to 30 carbon atoms or an arylamine group of 6 to 60 carbon atoms substituted with an alkyl group of 1 to 10 carbon atoms or unsubstituted.

In one embodiment of the present specification, R3, R1 "and R2" are the same as or different from each other, and each is independently hydrogen, deuterium, an alkyl group of 1 to 6 carbon atoms substituted with an aryl group of 6 to 20 carbon atoms or unsubstituted, a trialkylsilyl group of 1 to 20 carbon atoms, a triarylsilyl group of 6 to 50 carbon atoms, an aryl group of 6 to 20 carbon atoms, an N-containing aliphatic heterocyclic group of 2 to 20 carbon atoms substituted with an alkyl group of 1 to 6 carbon atoms or an aryl group of 6 to 20 carbon atoms or an arylamine group of 6 to 40 carbon atoms substituted with an alkyl group of 1 to 6 carbon atoms or unsubstituted.

In one embodiment of the present specification, R1 "and R2" are the same as or different from each other, and each independently represents hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms which is substituted with an aryl group having 6 to 20 carbon atoms or unsubstituted, a trialkylsilyl group having 1 to 20 carbon atoms, a triarylsilyl group having 6 to 50 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 40 carbon atoms.

The above-mentioned R3, R1 "and R2" and the adjacent substituents are bonded to each other, and means that 2 of the adjacent R3, 2 of the adjacent R1 "or 2 of the adjacent R2" are bonded to each other.

In one embodiment of the present specification, R3 is hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms, an arylamine group having 6 to 40 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, or an N-containing aliphatic heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R3 is hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms, an arylamine group having 6 to 40 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, or a group represented by the above chemical formula 2-a.

In one embodiment of the present specification, R1, R1 "and R2" are the same or different from each other and are each independently hydrogen, deuterium, methyl, tert-butyl, isopropyl substituted or unsubstituted with phenyl, trimethylsilyl, triphenylsilyl, phenyl or diphenylamino.

In one embodiment of the present description, R3 is hydrogen, deuterium, methyl, diphenylamino substituted or unsubstituted with t-butyl, hexahydrocarbazolyl substituted or unsubstituted with methyl or phenyl, indenoindolyl substituted or unsubstituted with methyl, benzofuroindolyl, or benzothienoindolyl.

In one embodiment of the present specification, R1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted trialkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted triarylsilyl group having 6 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms, or 2 of adjacent R1 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms, or one of R1 and R4 is bonded to each other to form a substituted or unsubstituted N-containing five-membered ring.

In one embodiment of the present specification, R1 is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, a trialkylsilyl group having 1 to 30 carbon atoms, a triarylsilyl group having 6 to 60 carbon atoms, an aryl group having 6 to 30 carbon atoms, an N-containing aliphatic heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms, or an arylamine group having 6 to 60 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, or 2 of adjacent R1 are bonded to each other to form an aliphatic hydrocarbon ring having 5 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, or one of R1 and R4 is bonded to each other to form a substituted or unsubstituted N-containing five-membered ring.

In one embodiment of the present specification, R1 is hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 1 to 20 carbon atoms, a triarylsilyl group having 6 to 50 carbon atoms, an aryl group having 6 to 20 carbon atoms, an N-containing aliphatic heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 40 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, or 2 of adjacent R1 are bonded to each other to form an aliphatic hydrocarbon ring having 5 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, or one of R1 and R4 is bonded to each other to form a substituted or unsubstituted N-containing five-membered ring.

In one embodiment of the present specification, R1 is hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 1 to 20 carbon atoms, a triarylsilyl group having 6 to 50 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 40 carbon atoms, or 2 of adjacent R1 are bonded to each other to form an aliphatic hydrocarbon ring having 5 to 20 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, or one of R1 and R4 is bonded to each other to form a substituted or unsubstituted N-containing five-membered ring.

In one embodiment of the present specification, R1 is hydrogen, deuterium, methyl, tert-butyl, isopropyl, trimethylsilyl, phenyl, or diphenylamino substituted or unsubstituted with phenyl, or 2 of adjacent R1 are bonded to each other to form a cyclohexene ring substituted or unsubstituted with methyl, a cyclopentene ring substituted or unsubstituted with methyl, a bicyclo [2.2.1] heptene ring substituted or unsubstituted with methyl, or a bicyclo [2.2.2] octene ring substituted or unsubstituted with methyl, or one of R1 and R4 are bonded to each other to form an N-containing five-membered ring.

In one embodiment of the present specification, R4 is i) a substituted or unsubstituted aryl group of 6 to 30 carbon atoms, to which an aliphatic hydrocarbon ring is fused or unfused, or ii) is combined with R1 to form a substituted or unsubstituted N-containing ring.

In one embodiment of the present specification, R4 is an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an arylalkyl group having 6 to 60 carbon atoms, or a group represented by the following chemical formula 2-D, or is bonded to R1 to form an N-containing five-membered ring which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 30 carbon atoms.

[ chemical formula 2-D ]

In the above chemical formula 2-D,

b1 is an aliphatic hydrocarbon ring or an aliphatic heterocyclic ring,

any one of R11 to R14 is a position bonded to the above chemical formulae A-4 to A-7, and the others are the same or different from each other, and each independently is hydrogen, deuterium, or a substituted or unsubstituted alkyl group,

r15 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group,

r15 is an integer of 0 or more, and when R15 is 2 or more, R15 may be the same or different from each other.

In one embodiment of the present specification, R4 in the above chemical formulae a-4 and a-5 is 1) a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, to which an aliphatic hydrocarbon ring is fused or unfused, or 2) is combined with R1 to form a substituted or unsubstituted N-containing five-membered ring. The above-mentioned N-containing five-membered ring means a ring in which the total number of carbons and N participating in ring formation is 5, including a case where an additional ring is fused in the formed ring.

In one embodiment of the present specification, R4 in the above chemical formulae a-4 and a-5 is an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an arylalkyl group having 6 to 60 carbon atoms, or a group represented by the above chemical formula 2-D, or is bonded to R1 to form an N-containing five-membered ring substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R4 of the above chemical formulae a-4 and a-5 is a phenyl group substituted or unsubstituted with a tert-butyl group or a phenylisopropyl group, a [1,1' -biphenyl ] -2-yl group substituted or unsubstituted with a tert-butyl group, or a group represented by the above chemical formula 2-D, or a phenyl group substituted or unsubstituted with a tert-butyl group and combined with R1 to form an N-containing five-membered ring.

In one embodiment of the present specification, R4 in the above chemical formulae A-6 and A-7 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, to which an aliphatic hydrocarbon ring is fused or unfused.

In one embodiment of the present specification, R4 in the above chemical formulae a-6 and a-7 is an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an arylalkyl group having 6 to 60 carbon atoms, or a group represented by the above chemical formula 2-D.

In one embodiment of the present specification, R4 in the above chemical formulae A-6 and A-7 is a phenyl group substituted or unsubstituted with a tert-butyl group or a phenylisopropyl group, a [1,1' -biphenyl ] -2-yl group substituted or unsubstituted with a tert-butyl group, or a group represented by the above chemical formula 2-D.

In one embodiment of the present specification, R5 in the above chemical formulae a-4 to a-7 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a group represented by the above chemical formula 2-D.

In one embodiment of the present specification, R5 in the above chemical formulae a-4 to a-7 is an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an arylalkyl group having 6 to 60 carbon atoms, or a group represented by the above chemical formula 2-D.

In one embodiment of the present specification, R5 of the above chemical formulae A-4 to A-7 is phenyl substituted or unsubstituted with tert-butyl or phenylisopropyl, [1,1' -biphenyl ] -2-yl substituted or unsubstituted with tert-butyl, or a group represented by the above chemical formula 2-D.

In one embodiment of the present specification, B1 is an aliphatic hydrocarbon ring having 6 to 20 carbon atoms.

In one embodiment of the present description, B1 is a cyclopentene ring, a cyclohexene ring or a cycloheptene ring.

In one embodiment of the present specification, B1 is a cyclopentene ring.

In one embodiment of this specification, R11 is the position attached to formulas A-4 through A-7 above.

In one embodiment of this specification, R12 is the position attached to formulas A-4 through A-7 above.

In one embodiment of this specification, R13 is the position attached to formulas A-4 through A-7 above.

In one embodiment of this specification, R14 is the position attached to formulas A-4 through A-7 above.

In one embodiment of the present specification, the remaining groups of R11 to R14, which are not linked to the above chemical formulae a-4 to a-7, are the same or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, the remaining groups of R11 to R14 not linked to the above formulae a-4 to a-7, which are the same or different from each other, are each independently hydrogen, deuterium, or methyl.

In one embodiment of the present specification, R15 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, R15 is hydrogen, deuterium, or methyl.

In one embodiment of the present specification, r15 is an integer from 0 to 20.

In one embodiment of the present specification, r15 is an integer from 0 to 10.

In one embodiment of the present specification, r15 is an integer from 1 to 4.

In one embodiment of the present specification, r1 "and r2" are integers from 0 to 20.

In one embodiment of the present specification, r1 "and r2" are integers of 0 to 10.

In one embodiment of the present specification, r1 "and r2" are integers of 0 to 5.

In one embodiment of the present specification, the chemical formula a is represented by the following chemical formula a-8.

[ chemical formula A-8]

In the above chemical formula A-8,

r3 to R5 and R3 are as defined in formula A,

x10 is C or Si,

r1 '", R2'", Z7 and Z8, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, or a substituted or unsubstituted amine group, or combine with adjacent substituents to each other to form a substituted or unsubstituted ring,

r1 '"is an integer of 0 to 3, r 2'" is an integer of 0 to 3, and when r1 '"and r 2'" are each 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present disclosure, when R1'″ is 2 or more, the plurality of R1' ″ may be the same as or different from each other. In another embodiment, when R2 '"is 2 or more, the plurality of R2'" are the same as or different from each other.

In one embodiment of the present specification, Z7 and Z8, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, Z7 and Z8 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring having 5 to 30 carbon atoms.

In one embodiment of the present specification, Z7 and Z8 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted ring having 5 to 20 carbon atoms.

In one embodiment of the present specification, Z7 and Z8, which are the same or different from each other, are each independently a methyl group or a phenyl group, or are combined with each other while being a phenyl group to form a fluorene ring.

In one embodiment of the present specification, R1"', R2"', and R3, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted amine group, or combine with each other with an adjacent substituent to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R1'″, R2' ″, and R3 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms, or a ring having 2 to 30 carbon atoms which is substituted or unsubstituted is formed by combining adjacent substituents with each other.

In one embodiment of the present specification, R1 '", R2'", and R3 are the same as or different from each other, and each is independently hydrogen, deuterium, an alkyl group of 1 to 6 carbon atoms substituted or unsubstituted with an aryl group of 6 to 20 carbon atoms, a cycloalkyl group of 3 to 20 carbon atoms, an alkoxy group of 1 to 6 carbon atoms substituted or unsubstituted with a halogen group, an aryl group of 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group of 1 to 6 carbon atoms, an N-containing heterocyclic group of 2 to 25 carbon atoms substituted or unsubstituted with an alkyl group of 1 to 6 carbon atoms or an aryl group of 6 to 20 carbon atoms, or an arylamine group of 6 to 40 carbon atoms substituted or unsubstituted with an alkyl group of 1 to 6 carbon atoms, or combine with each other with an adjacent substituent to form a ring of carbon number 5 to 20 which is substituted or unsubstituted with an alkyl group of carbon number 1 to 6 or an aryl group of carbon number 2 to 20.

In one embodiment of the present specification, R1 '"and R2'", which are the same as or different from each other, are each independently hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms substituted with an aryl group having 6 to 20 carbon atoms or unsubstituted with an aryl group having 2 to 20 carbon atoms, or combine with each other with an adjacent substituent to form a ring having 5 to 20 carbon atoms substituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 2 to 20 carbon atoms or unsubstituted.

In one embodiment of the present specification, R1 '"and R2'", which are the same or different from each other, are each independently hydrogen, deuterium, tert-butyl, isopropyl substituted or unsubstituted with phenyl, or combine with each other with adjacent substituents to form a ring of carbon number 5 to 20 substituted or unsubstituted with an alkyl group of carbon number 1 to 6 or an aryl group of carbon number 2 to 20.

In one embodiment of the present specification, R3 in the above chemical formula a-8 is hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 6 carbon atoms which is substituted or unsubstituted with a halogen group, an N-containing heterocyclic group having 2 to 25 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 40 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, R3 in the above chemical formula a-8 is hydrogen, deuterium, methyl, tert-butyl, adamantyl, methoxy substituted or unsubstituted with fluorenyl, hexahydrocarbazolyl substituted or unsubstituted with methyl or tert-butyl, or diphenylamino substituted or unsubstituted with tert-butyl.

When R1"', R2"', and R3 combine with the adjacent substituent to form a substituted or unsubstituted ring, a ring selected from the following structures is specifically formed.

In the above-described structure, the first and second electrodes,

r1', R2', and R3 refer to the carbon participating in ring formation,

y6 to Y9, equal to or different from each other, are each independently O, S or N (Ra2),

r21 to R27 and Ra2, equal to or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

cy2 is a cycloaliphatic ring which,

cy3 is an aliphatic or aromatic ring,

p5 is an integer of 1 to 3,

when r21 is an integer of 0 to 8, r22 and r26 are integers of 0 to 4, r25 and r27 are integers of 0 or more, and r21, r22, and r25 to r27 are each 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, when R21 is 2 or more, a plurality of R21 s are the same as or different from each other. In another embodiment, when R22 is 2 or more, the plurality of R22 are the same as or different from each other. In another embodiment, when R25 is 2 or more, the plurality of R25 are the same as or different from each other. In another embodiment, when R26 is 2 or more, the plurality of R26 are the same as or different from each other. In another embodiment, when R27 is 2 or more, the plurality of R27 are the same as or different from each other.

In the above structure, is a position fused with the above chemical formula a-8.

In one embodiment of the present specification, p5 is 1 or 2.

In one embodiment of the present specification, r25 is an integer from 0 to 20.

In one embodiment of the present specification, r27 is an integer from 0 to 10.

In one embodiment of the present specification, r27 is an integer from 0 to 20.

In one embodiment of the present specification, r27 is an integer from 0 to 10.

In one embodiment of the present specification, R21 to R27 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R21 to R27, which are the same or different from each other, are each independently hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R21 to R27, which are the same or different from each other, are each independently hydrogen, deuterium, methyl, or tert-butyl.

In one embodiment of the present specification, R25 and R27 are the same as or different from each other, and each is independently hydrogen or deuterium.

In one embodiment of the present specification, Ra2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ra2 is phenyl.

In one embodiment of the present specification, Cy2 is an aliphatic hydrocarbon ring. Specifically a cycloalkane ring.

In one embodiment of the present specification, Cy2 is an aliphatic hydrocarbon ring having 5 to 20 carbon atoms.

In one embodiment of the present specification, Cy2 is a cyclohexane ring.

In one embodiment of the present specification, Cy3 is a cycloolefin ring or an aromatic hydrocarbon ring.

In one embodiment of the present specification, Cy3 is a cyclopentene ring, a cyclohexene ring or a benzene ring.

In one embodiment of the present specification, the above descriptions about R4 and R5 of the formulas A-4 to A-7 can be applied to R4 and R5 of the formula A-8.

In one embodiment of the present specification, R4 and R5 of the above chemical formula a-8, which are the same or different from each other, are each independently a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R4 and R5 in the above chemical formula a-8 are the same as or different from each other, and each independently represents a substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R4 and R5 in the above chemical formula a-8 are the same as or different from each other, and each independently represents a substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a group represented by the following chemical formula 2-E.

In one embodiment of the present specification, R4 and R5 of the above chemical formula a-8 are the same as or different from each other, and each independently represents a cycloalkyl group having 1 to 20 carbon atoms; an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, an arylalkyl group having 6 to 60 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or a heterocyclic group having 2 to 30 carbon atoms and to which an aliphatic hydrocarbon ring having 5 to 20 carbon atoms is fused or not fused; or a heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, R4 and R5 of the above chemical formula a-8 are the same as or different from each other, and each independently represents a cycloalkyl group having 1 to 20 carbon atoms; an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, an arylalkyl group having 6 to 60 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or a heterocyclic group having 2 to 30 carbon atoms; a heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms; or a group represented by the following chemical formula 2-E.

[ chemical formula 2-E ]

In the above-mentioned chemical formula 2-E,

cy4 is an aliphatic or aromatic ring,

any one of R31 to R34 is a position bonded to the above chemical formula A-8, and the others are the same or different from each other, and each independently is hydrogen, deuterium, or a substituted or unsubstituted alkyl group,

r35 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group,

r35 is an integer of 0 or more, and when R35 is 2 or more, R35 may be the same or different from each other.

In one embodiment of the present specification, R4 and R5 of the above chemical formula A-8, which are the same or different from each other, are each independently an adamantyl group; phenyl unsubstituted or substituted by tert-butyl, phenylisopropyl, adamantyl or pyridyl; [1,1' -biphenyl ] -2-yl substituted or unsubstituted with tert-butyl; a dimethyl fluorenyl group; dibenzofuranyl substituted or unsubstituted with tert-butyl; or a group represented by the above chemical formula 2-E.

In one embodiment of the present specification, Cy4 is an aliphatic hydrocarbon ring having 5 to 20 carbon atoms or an aromatic heterocyclic ring having 2 to 20 carbon atoms.

In one embodiment of the present specification, Cy4 is a cyclohexene ring or furan ring.

In one embodiment of the present specification, R31 is a position bonded to the above chemical formula A-8.

In one embodiment of the present specification, R32 is a position bonded to the above chemical formula A-8.

In one embodiment of the present specification, R33 is a position bonded to the above chemical formula A-8.

In one embodiment of the present specification, R34 is a position bonded to the above chemical formula A-8.

In one embodiment of the present specification, the remaining groups of R31 to R34, which are not linked to the above chemical formula a-8, are the same or different from each other, and each independently is hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, the remaining groups of R31 to R34, which are not linked to the above chemical formula a-8, are the same or different from each other, and are each independently hydrogen, deuterium, or methyl.

In one embodiment of the present specification, the remaining groups of R31 to R34, which are not linked to the above chemical formula a-8, are the same or different from each other, and are each independently hydrogen or deuterium.

In one embodiment of the present specification, R35 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present description, R35 is hydrogen, deuterium, methyl, or tert-butyl.

In one embodiment of the present specification, r35 is an integer from 0 to 20.

In one embodiment of the present specification, r35 is an integer from 0 to 10.

In one embodiment of the present specification, r35 is an integer from 0 to 2.

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

In one embodiment of the present specification, the compound represented by the above chemical formula a is any one selected from the following compounds. Specifically, the compound represented by the above chemical formula A-2 or A-3 is any one selected from the following compounds.

In one embodiment of the present specification, the compound represented by the above chemical formula a is any one selected from the following compounds. Specifically, the compound represented by any one of the above chemical formulae a-4 to a-7 is any one selected from the following compounds.

In one embodiment of the present specification, the compound represented by the above chemical formula a is any one selected from the following compounds. Specifically, the compound represented by the above chemical formula a-8 is any one selected from the following compounds.

In one embodiment of the present specification, 1 or more compounds among the compounds represented by the above chemical formula 1 and compound a may include 1 or more deuterium. The compound containing deuterium can be produced by a known deuteration reaction. As an example, the compound represented by chemical formula 1 is formed using a deuterated compound as a precursor, or deuterium may be introduced into the compound by a hydrogen-deuterium exchange reaction using a deuterated solvent under an acid catalyst.

In the case where the compound of the above chemical formula 1 contains deuterium, the efficiency and lifetime of the device are improved. Specifically, in the case where hydrogen is replaced with deuterium, although the chemical properties of the compound are hardly changed, the physical properties of the deuterated compound are changed, so that the vibration level is lowered. Therefore, the compound substituted with deuterium can prevent the quantum efficiency from being reduced due to the reduction of the intermolecular van der waals force or the collision caused by the vibration between molecules. Furthermore, the stability of the compound can be improved by a stronger C-D bond compared to a C-H bond.

In the present specification, the degree of deuteration can be confirmed by a known method such as nuclear magnetic resonance spectroscopy (1H NMR) or GC/MS.

In one embodiment of the present invention, the compound of chemical formula 1 can be produced by a production method described later.

According to an embodiment of the present invention, the compound of the chemical formula a may be produced as shown in the following reaction formula 2. The following reaction formula 2 describes a synthesis process of a partial compound corresponding to the chemical formula a of the present application, but various compounds corresponding to the chemical formula a of the present application can be synthesized by the synthesis process shown in the following reaction formula 2, substituents can be combined by a method known in the art, and the kind, position and number of substituents can be changed according to a technique known in the art.

[ reaction formula 2]

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

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

The organic layer of the organic light-emitting device in the present specification may be formed of a single layer structure including a light-emitting layer, or may be formed of 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 which performs both hole transport and hole injection, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer which performs both electron transport and electron injection, a hole suppression layer, and the like as organic layers. However, the structure of the organic light emitting device is not limited thereto, and a smaller number or a larger number of organic layers may be included.

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

In the organic light emitting device according to an embodiment of the present specification, the dopant may be included in the light emitting layer in an amount of 0.1 to 50 parts by weight, based on 100 parts by weight of the host. According to another embodiment, the dopant may be included in the light emitting layer in an amount of 1 to 30 parts by weight, based on 100 parts by weight of the host. When within the above range, energy transfer from the host to the dopant effectively occurs.

The structure of the organic light emitting device of the present invention may have the structure shown in fig. 1 to 3, but is not limited thereto.

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

Fig. 2 illustrates a structure of an organic light-emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1. In the structure described above, the above-described compound may be contained in the above-described hole injection layer 5, hole transport layer 6, light emitting layer 7, or electron transport layer 8.

Fig. 3 illustrates a structure of an organic light-emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 4 are stacked in this order on a substrate 1. In the structure described above, the above-described compound may be contained in the above-described hole injection layer 5, hole transport layer 6, light emitting layer 7, or electron transport layer 8.

For example, the organic light emitting device of the present specification can be manufactured as follows: the organic el display device is manufactured by forming an anode by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate by a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, and an electron injection layer on the anode, and depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.

The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer simultaneously injecting and transporting electrons, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer simultaneously injecting and transporting electrons, a hole blocking layer, and the like, in addition to the light emitting layer including the compound represented by chemical formula 1 and the compound represented by chemical formula a, but is not limited thereto and may have a single-layer structure. The organic layer can be produced as a smaller number of layers by a solvent process (solvent process) other than the vapor deposition method, for example, spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method using various polymer materials.

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

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

The hole injection layer is a layer that functions to smoothly inject holes from the anode into the light-emitting layer, and the hole injection substance is a substance that can inject holes from the anode well at a low voltage, and preferably, the HOMO (highest occupied molecular orbital) of the hole injection substance is interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrine), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.

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 is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

An electron inhibiting layer may be provided between the hole transport layer and the light emitting layer. The electron-suppressing layer may use the above-mentioned compounds or materials known in the art.

The organic light emitting device of the present invention may include an additional light emitting layer in addition to the light emitting layer including the compound of chemical formula 1 and the compound of chemical formula a. In this case, the light-emitting layer may emit red, green or blue light, and may be formed of a phosphorescent substance or a fluorescent substance. The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is

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

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

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

As the light emitting dopant of the additional light emitting layer, piqir (bis (1-phenylisoquinoline) iridium acetylacetonate, bis (1-phenylisoquinoline) acetylateeridium), PQIr (acac) (bis (1-phenylquinoline) iridium acetylacetonate, bis (1-phenylquinoline) iridium acetate iodide, PQIr (tris (1-phenylquinoline) iridium, tris (1-phenylquinoline) ir iodide, PtOEP (platinum octaethylporphyrin, octaethylporphyrin platinum), or other phosphorescent materials, or Alq3 (tris (8-hydroxyquinoline) aluminum, tris (8-hydroxyquinoline) aluminum), and other fluorescent materials can be used, but not limited thereto. When the light-emitting layer emits green light, Ir (ppy) can be used as a light-emitting dopant₃Phosphorescent substances such as tris (2-phenylpyridinium) iridium and fac tris (2-phenylpyridinium) iridium, and Alq₃(tris (8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) aluminum m) and other fluorescent substances, but the fluorescent substance is not limited thereto. When the light-emitting layer emits blue light, a phosphorescent substance such as (4,6-F2ppy)2Irpic or a fluorescent substance such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), Distyrylbenzene (DSB), Distyrylarylene (DSA), PFO-based polymer, PPV-based polymer can be used as the light-emitting dopant, but the light-emitting dopant is not limited thereto.

The light emitting layer including the compound of chemical formula 1 and the compound of chemical formula a may include an additional host and/or an additional dopant in addition to the above compounds. The host and dopant materials that may be additionally included are the same as the host material and the light emitting dopant material of the additional light emitting layer described above.

In one embodiment of the present description, a hole-inhibiting layer may be provided between the electron-transporting layer and the light-emitting layer, and a material known in the art may be used for the hole-inhibiting layer.

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

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

Azole,

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

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

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

Modes for carrying out the invention

The present specification will be described in more detail with reference to the following examples. However, the following examples are only for illustrating the present specification and are not intended to limit the present specification.

< Synthesis example >

The above definitions of z, z1, z2 and z6 are the same as those in chemical formula 1.

Synthesis example 1 Synthesis of Compound 1

Synthesis examples 1-1 Synthesis of Compound 1-a

1-bromo-2-fluorodibenzo [ b, d ]]Furan (80g, 302mmol) and (5-chloro-2-hydroxyphenyl) boronic acid (52.0g, 302mmol) were dissolved in tetrahydrofuran (THF, 1500ml), and Pd (PPh) was added₃)₄(6.97g, 6.0mmol) and 2M of K₂CO₃300ml of the aqueous solution was stirred under reflux for 24 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure, and the residue was purified by column chromatography to give compound 1-a (63g, yield 67%).

Synthesis examples 1-2 Synthesis of Compound 1-b

Compound 1-a (63g, 201mmol) was dissolved in dimethylformamide (D)MF, 1000ml), K was added₂CO₃(83.5g, 604mmol) and stirred at reflux for 2 hours. After the reaction solution was cooled, it was poured into 3L of distilled water to produce a solid. The solid was filtered, dissolved in chloroform, extracted several times with water, and the organic layer was dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure, and purification was performed by column chromatography to obtain compound 1-b (46g, yield 78%).

Synthesis examples 1-3 Synthesis of Compound 3

Compound 1-b (46g, 157mmol) and bis (pinacolato) diboron (48g, 189mmol), potassium acetate (KOAc) (31g, 314mmol) and 400ml of diboron

The alkanes (Dioxane) were added to the flask together and dispersed. Bis (dibenzylideneacetone) palladium (0) (Pd (dba))₂) (1.81g, 3.1mmol), Tricyclohexylphosphine (PCy)₃) (1.76g, 6.3mmol) and then stirred under reflux for 24 hours. After the reaction is finished, the reaction product is distilled under reduced pressure to remove II

An alkane. After dissolving in chloroform, the mixture was extracted 3 times with distilled water, and the organic layer was distilled under reduced pressure to remove chloroform. Purification was performed by column chromatography to obtain compound 1. (42g, yield 70%)

Synthesis example 2 Synthesis of Compound 2

Synthesis example 2-1 Synthesis of Compound 2-a

In Synthesis example 1-1, compound 2-a was obtained by the same method using 4-bromo-3-fluorodibenzo [ b, d ] furan and (4-chloro-2-hydroxyphenyl) boronic acid.

Synthesis example 2-2 Synthesis of Compound 2-b

In Synthesis example 1-2, Compound 2-b was obtained from Compound 2-a by the same method.

Synthesis examples 2-3 Synthesis of Compound 2

In Synthesis examples 1 to 3, Compound 2 was obtained from Compound 2-b by the same method.

Synthesis example 3 Synthesis of Compound 3

Synthesis example 3-1 Synthesis of Compound 3-a

In Synthesis example 1-1, compound 3-a was obtained by the same method using 4-bromo-3-fluorodibenzo [ b, d ] furan.

Synthesis example 3-2 Synthesis of Compound 3-b

In Synthesis example 1-2, Compound 3-b was obtained from Compound 3-a by the same method.

Synthesis examples 3-3 Synthesis of Compound 3

In Synthesis examples 1 to 3, Compound 3 was obtained from Compound 3-b by the same method.

Synthesis example 4 Synthesis of Compound 4

Synthesis example 4-1 Synthesis of Compound 4-a

In Synthesis example 1-1, compound 4-a was obtained by the same method using 2-bromo-3-fluorodibenzo [ b, d ] furan.

Synthesis example 4-2 Synthesis of Compound 4-b

In Synthesis example 1-2, Compound 4-b was obtained from Compound 4-a by the same method.

Synthesis examples 4-3 Synthesis of Compound 4

In Synthesis examples 1 to 3, Compound 4 was obtained from Compound 4-b by the same method.

Synthesis example 5 Synthesis of Compound 5

Synthesis example 5-1 Synthesis of Compound 5-a

In Synthesis example 1-1, compound 5-a was obtained by the same method using 3-bromo-2-fluorodibenzo [ b, d ] furan.

Synthesis example 5-2 Synthesis of Compound 5-b

In Synthesis example 1-2, Compound 5-b was obtained from Compound 5-a by the same method.

Synthesis examples 5-3 Synthesis of Compound 5

In Synthesis examples 1 to 3, Compound 5 was obtained from Compound 5-b by the same method.

Synthesis example 6 Synthesis of Compound 6

Synthesis example 6-1 Synthesis of Compound 6-a

In Synthesis example 1-1, compound 6-a was obtained in the same manner using 2-bromo-3-fluorodibenzo [ b, d ] furan and (6-chloro-2-hydroxyphenyl) boronic acid.

Synthesis example 6-2 Synthesis of Compound 6-b

In Synthesis example 1-2, Compound 6-b was obtained using Compound 6-a and by the same method.

Synthesis examples 6-3 Synthesis of Compound 6

In Synthesis examples 1 to 3, Compound 6 was obtained from Compound 6-b by the same method.

Synthesis example 7 Synthesis of Compound 7

Synthesis example 7-1 Synthesis of Compound 7-a

In Synthesis example 1-1, compound 7-a was obtained in the same manner using 2-bromo-4-chloro-3-fluorodibenzo [ b, d ] furan and (2-hydroxyphenyl) boronic acid.

Synthesis example 7-2 Synthesis of Compound 7-b

In Synthesis example 1-2, Compound 7-b was obtained from Compound 7-a by the same method.

Synthesis examples 7-3 Synthesis of Compound 7

In Synthesis examples 1 to 3, Compound 7 was obtained from Compound 7-b by the same method.

Synthesis example 8 Synthesis of Compound 8

Synthesis example 8-1 Synthesis of Compound 8-a

In Synthesis example 1-1, compound 8-a was obtained by the same method using 4-bromo-3-fluorodibenzo [ b, d ] furan.

Synthesis example 8-2 Synthesis of Compound 8-b

In Synthesis example 1-2, Compound 8-b was obtained from Compound 8-a by the same method.

Synthesis examples 8-3 Synthesis of Compound 8

In Synthesis examples 1 to 3, Compound 8 was obtained from Compound 8-b by the same method.

Synthesis example 9 Synthesis of Compound 9

Synthesis example 9-1 Synthesis of Compound 9-a

In Synthesis example 1-1, compound 9-a was obtained by the same method using 3-bromo-4-fluorodibenzo [ b, d ] furan and (6-chloro-2-hydroxyphenyl) boronic acid.

Synthesis example 9-2 Synthesis of Compound 9-b

In Synthesis example 1-2, Compound 9-b was obtained using Compound 9-a and by the same procedure.

Synthesis examples 9-3 Synthesis of Compound 9

In Synthesis examples 1 to 3, Compound 9 was obtained from Compound 9-b by the same method.

Synthesis example 10 Synthesis of Compound 10

Synthesis example 10-1 Synthesis of Compound 10-a

In Synthesis example 1-1, 4-bromo-1-chloro-3-fluorodibenzo [ b, d ] furan and 2-hydroxyphenylboronic acid were used to obtain compound 10-a by the same method.

Synthesis example 10-2 Synthesis of Compound 10-b

In Synthesis example 1-2, Compound 10-b was obtained from Compound 10-a by the same method.

Synthesis example 10-3 Synthesis of Compound 10

In Synthesis examples 1 to 3, Compound 10 was obtained from Compound 10-b by the same method.

Synthesis example 11 Synthesis of Compound 11

Synthesis example 11-1 Synthesis of Compound 11-a

Dibenzo [ b, d ] thiophen-2-ol (1 eq) was dissolved in DMF (2000ml) and N-bromosuccinimide (1 eq) dissolved in 500ml DMF was slowly added dropwise. After stirring at room temperature for 2 hours, 3000ml of water was added dropwise. When a solid was formed, the solid was filtered, dissolved in chloroform, and extracted with distilled water several times. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Purification was performed by column chromatography to give compound 11-a.

Synthesis example 11-2 Synthesis of Compound 11-b

In Synthesis example 1-1, Compound 11-b was obtained by the same procedure using Compound 11-a and (5-chloro-2-fluorophenyl) boronic acid.

Synthesis examples 11-3 Synthesis of Compound 11-c

In Synthesis example 1-2, Compound 11-c was obtained from Compound 11-b by the same method.

Synthesis examples 11-4 Synthesis of Compound 11

In Synthesis examples 1 to 3, Compound 11 was obtained from Compound 11-c by the same method.

Synthesis example 12 Synthesis of Compound 12

Synthesis example 12-1 Synthesis of Compound 12-a

In Synthesis example 1-1, compound 12-a was obtained using 4-bromo-3-fluorodiphenylfluorene and (5-chloro-2-hydroxyphenyl) boronic acid and by the same method.

Synthesis example 12-2 Synthesis of Compound 12-b

In Synthesis example 1-2, Compound 12-b was obtained using Compound 12-a and by the same procedure.

Synthesis examples 12-3 Synthesis of Compound 12

In Synthesis examples 1 to 3, Compound 12 was obtained using Compound 12-b and by the same method.

Synthesis example 13 Synthesis of Compound 13

Synthesis example 13-1 Synthesis of Compound 13-a

In Synthesis example 1-1, 1-bromo-2-iodo-3-fluorobenzene and 2M NA were used₂CO₃Compound 13-a was obtained as an aqueous solution by the same method.

Synthesis example 13-2 Synthesis of Compound 13-b

In Synthesis example 1-2, Compound 13-b was obtained using Compound 13-a and by the same procedure.

Synthesis example 13-3 Synthesis of Compound 13-c

In Synthesis example 1-1, Compound 13-c was obtained using Compound 13-b and 2-Nitroboronic acid and by the same procedure.

Synthesis examples 13-4 Synthesis of Compound 13-d

The compound 13-c (1 equivalent) and PPh₃(3 eq.) after dissolving in 600ml of o-dichlorobenzene, stirring under reflux for 8 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the mixture was dissolved in chloroform and extracted with distilled water several times. The organic layer was dried over anhydrous magnesium sulfate, and then the chloroform was removed by distillation under the reduced pressure. Purification was performed by column chromatography to obtain compound 13-d (yield 60%).

Synthesis examples 13-5 Synthesis of Compound 13-e

Compound 13-d (1 eq) and iodobenzene (1 eq) were dissolved in 250ml of DMF and CS was added₂CO₃(2 equiv.) and CuI (0.1 equiv.). After warming to 120 ℃, the mixture was stirred for 16 hours. After cooling the reaction solution, 1L of ethyl acetate was added, the mixture was transferred to a separatory funnel, extracted 1 time with an aqueous ammonia solution, and distilled 1LThe water extraction was performed 3 times in total. The organic layer was collected, treated with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. Purification was performed by column chromatography to give compound 13-e. (yield 57%)

Synthesis examples 13-6 Synthesis of Compound 13

In Synthesis examples 1 to 3, Compound 13 was obtained using Compound 13-e and by the same method.

Synthesis example 14 Synthesis of Compound 14

Synthesis example 14-1 Synthesis of Compound 14-a

In Synthesis example 1-1, compound 14-a was obtained using 1-bromo-2-fluorodimethylfluorene and by the same method.

Synthesis example 14-2 Synthesis of Compound 14-b

In Synthesis example 1-2, Compound 14-b was obtained using Compound 14-a and by the same procedure.

Synthesis examples 14-3 Synthesis of Compound 14

In Synthesis examples 1 to 3, Compound 14 was obtained using Compound 14-b in the same manner.

Synthesis example 15 Synthesis of Compound 15

Synthesis example 15-1 Synthesis of Compound 15-a

Anthracene (20g) and AlCl₃(4g) Is added to C₆D₆(600ml) was stirred for 2 hours. After the reaction is finished, D is added₂O (30ml), and after stirring for 30 minutes, trimethylamine (2.4ml) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was washed with MgSO₄After drying, useEthyl acetate was recrystallized to obtain compound 15-a (15g, yield 75%). The final compound was confirmed by mass spectrometry (mass). In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:188.3, experiment M/s (M + H) 187.3-189.3%]

Synthesis example 15-2 Synthesis of Compound 15-b

In Synthesis example 11-1, Compound 15-b was obtained from Compound 15-a by the same procedure.

Synthesis example 15-3 Synthesis of Compound 15-c

In Synthesis example 1-1, Compound 15-c was obtained using Compound 15-b and by the same method.

Synthesis examples 15-4 Synthesis of Compound 15

In Synthesis example 11-1, Compound 15 was obtained from Compound 15-c by the same method.

Synthesis example 16 Synthesis of Compound 16

Synthesis example 16-1 Synthesis of Compound 16-a

In Synthesis example 1-1, Compound 16-a was obtained using Compound 15-b and 1-naphthalene boronic acid and by the same method.

Synthesis example 16-2 Synthesis of Compound 16

In Synthesis example 11-1, Compound 16 was obtained using Compound 16-a and by the same procedure.

Synthesis example 17 Synthesis of Compound 17

Synthesis example 17-1 Synthesis of Compound 17-a

In Synthesis example 1-1, Compound 17-a was obtained using Compound 15-b and 2-Naphthylboronic acid and by the same method.

Synthesis example 17-2 Synthesis of Compound 17

In Synthesis example 11-1, Compound 17 was obtained using Compound 17-a and by the same procedure.

Synthesis example 18 Synthesis of Compound 18

Synthesis example 18-1 Synthesis of Compound 18-a

In Synthesis example 1-1, Compound 18-a was obtained using Compound 15-b and 2-dibenzo [ b, d ] furanboronic acid and by the same method.

Synthesis example 18-2 Synthesis of Compound 18

In Synthesis example 11-1, Compound 18 was obtained using Compound 18-a and by the same procedure.

Synthesis example 19 Synthesis of BH-A

In Synthesis example 1-1, BH-A was obtained using compound 15 and compound 1 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of m/s:510.6, experiment M/s (M + H) 508.6-511.6 ]

Synthesis example 20 Synthesis of BH-B

In Synthesis example 1-1, BH-B was obtained using compound 16 and compound 1 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:560.7, experiment M/s (M + H) 558.7-561.7 ]

Synthesis example 21 Synthesis of BH-C

In Synthesis example 1-1, BH-C was obtained using compound 15 and compound 2 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:510.6, experiment M/s (M + H) 508.6-511.6 ]

Synthesis example 22 Synthesis of BH-D

In Synthesis example 1-1, BH-D was obtained using compound 16 and compound 3 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:560.7, experiment M/s (M + H) 558.7-561.7 ]

Synthesis example 23 Synthesis of BH-E

In Synthesis example 1-1, BH-E was obtained using compound 15 and compound 4 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:510.6, experiment M/s (M + H) 508.6-511.6 ]

Synthesis example 24 Synthesis of BH-F

In Synthesis example 1-1, BH-F was obtained using compound 15 and compound 5 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:510.6, experiment M/s (M + H) 508.6-511.6 ]

Synthesis example 25 Synthesis of BH-G

In Synthesis example 1-1, BH-G was obtained using compound 15 and compound 6 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:510.6, experiment M/s (M + H) 508.6-511.6 ]

Synthesis example 26 Synthesis of BH-H

In Synthesis example 1-1, BH-H was obtained using compound 15 and compound 7 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:510.6, experiment M/s (M + H) 508.6-511.6 ]

Synthesis example 27 Synthesis of BH-I

In Synthesis example 1-1, BH-I was obtained using compound 15 and compound 8 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:510.6, experiment M/s (M + H) 508.6-511.6 ]

Synthesis example 28 Synthesis of BH-J

In Synthesis example 1-1, BH-J was obtained using compound 15 and compound 9 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:510.6, experiment M/s (M + H) 508.6-511.6 ]

Synthesis example 29 Synthesis of BH-K

In Synthesis example 1-1, BH-K was obtained using compound 17 and compound 10 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:560.7, experiment M/s (M + H) 558.7-561.7 ]

Synthesis example 30 Synthesis of BH-L

In Synthesis example 1-1, BH-L was obtained using compound 18 and compound 9 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:600.6, experiment M/s (M + H) 588.6-601.6 ]

Synthesis example 31 Synthesis of BH-M

In Synthesis example 1-1, BH-M was obtained using compound 15 and compound 11 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:526.7, experiment M/s (M + H) 524.7-527.7 ]

Synthesis example 32 Synthesis of BH-N

In Synthesis example 1-1, BH-N was obtained using compound 15 and compound 12 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:660.8, experiment M/s (M + H) 658.86-661.8 ]

Synthesis example 33 Synthesis of BH-O

In Synthesis example 1-1, BH-O was obtained using compound 15 and compound 13 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:585.7, experiment M/s (M + H) 583.7-586.7 ]

Synthesis example 34 Synthesis of BH-P

In Synthesis example 1-1, BH-P was obtained using compound 15 and compound 14 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:536.7, experiment M/s (M + H) 534.7-537.7 ]

Synthesis example 35 Synthesis of BH-Q

In Synthesis example 15-1, BH-Q was obtained by the same method using BH-B. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:584.8, experiment M/s (M + H) 580.8-585.8 ]

Synthesis example 36 Synthesis of BH-R

Synthesis example 36-1 Synthesis of Compound 19-a

In Synthesis example 15-1, 9-naphthalene-1-anthracene was used to obtain compound 19-a in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:320.5, experiment M/s (M + H) 318.5-321.5 ]

Synthesis example 36-2 Synthesis of Compound 19-b

In Synthesis example 11-1, Compound 19-b was obtained using Compound 19-a and by the same procedure.

Synthesis example 36-3. Synthesis of BH-R

In Synthesis example 1-1, BH-R was obtained using compound 19-b and compound 1 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:575.7, experiment M/s (M + H) 574.7-576.7 ]

Synthesis example 37 Synthesis of BH-S

In Synthesis example 15-1, BH-S was obtained by the same method using BH-G. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:584.8, experiment M/s (M + H) 581.8-585.8 ]

Synthesis example 38 Synthesis of BH-T

Synthesis example 38-1 Synthesis of Compound 20-a

In Synthesis example 15-1, compound 20-a was obtained using 9-phenyl-anthracene and by the same method. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:268.4, experiment M/s (M + H) 265.4-269.4 ]

Synthesis example 38-2 Synthesis of Compound 20-b

In Synthesis example 11-1, Compound 20-b was obtained from Compound 20-a by the same procedure.

Synthesis example 38-3. Synthesis of BH-T

In Synthesis example 1-1, BH-T was obtained using compound 20-b and compound 6 in the same manner. The final compound was confirmed by mass spectrometry. In the deuterium substitution reaction, the molecular weight is shown as a distribution. [ calculation of M/s:523.7, experiment M/s (M + H) 520.7-524.7 ]

< Experimental example >

EXAMPLE 1 fabrication of organic light emitting device

A glass substrate on which ITO (indium tin oxide) was coated in a thickness of 150nm was placed in distilled water in which a detergent was dissolved, and washed with ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with nitrogen plasma for 5 minutes, the substrate was transported to a vacuum evaporator. On the ITO transparent electrode thus prepared, a hole injection layer was formed by thermal vacuum evaporation of the HAT-CN compound described below at a thickness of 5 nm. Subsequently, HTL1 was thermally vacuum-deposited at a thickness of 100nm, and HTL2 was thermally vacuum-deposited at a thickness of 10nm to form a hole transport layer. Next, the compound HB-A as a host and BD-A as a dopant (97: 3 by weight) were simultaneously vacuum-evaporated to form a light-emitting layer having a thickness of 20 nm. Subsequently, ETL was vacuum-evaporated to a thickness of 20nm to form an electron transport layer. Then, LiF was vacuum-evaporated to a thickness of 0.5nm to form an electron injection layer. Subsequently, aluminum was deposited to a thickness of 100nm to form a cathode, thereby manufacturing an organic light-emitting device.

The structures of the compounds used in the examples are shown below.

For the organic light emitting devices manufactured in the above examples 1 to 20 and comparative examples 1 to 3, at 10mA/cm²The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm²The time (LT) of 95% of the initial luminance was measured at the current density of (1), and the results are shown in table 1 below.

[ Table 1]

Examples 1 to 20 using the compound represented by chemical formula 1 of the present invention all showed low voltage and high efficiency characteristics as compared to comparative examples 1 to 3, and deuterium was substituted on anthracene, thereby showing that life was also excellent. Further, it can be confirmed from examples 17 to 20 that the lifetime of a device using the compound is significantly improved by increasing the deuterium substitution rate.

Comparative example 1 using a compound BH-1 substituted with dibenzofuran, it was confirmed that the driving voltage was high, and the efficiency and the lifetime were reduced as compared with examples 1 to 20. Further, the compound BH-2 used in comparative example 2 corresponds to the case where deuterium is contained at a substitution position other than anthracene in chemical formula 1, and brings about an increase in lifetime as compared with comparative example 1, but shows a short lifetime as compared with examples.

Further, the compound BH-3 used in comparative example 3 corresponds to a case where a heteroaromatic group containing an element having a smaller electronegativity than O (oxygen) is substituted at the position 9 of anthracene, and when such a compound is used, it is confirmed that the electron-withdrawing property is decreased, and the driving voltage and the efficiency lifetime are significantly reduced.

Claims

1. An organic light emitting device comprising:

an anode;

a cathode; and

an organic layer including a light-emitting layer between the anode and the cathode,

wherein the light emitting layer includes a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula a:

chemical formula 1

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

y101 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

y102 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group,

d is the deuterium, and the nitrogen is the hydrogen,

chemical formula 2

In the chemical formula 2,

w is O, S, NR or CR' R ",

c is an integer of 0 to 4,

is a position bound to the chemical formula 1,

chemical formula A

In the chemical formula A, the compound represented by the formula A,

2. The organic light emitting device according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 1-1 to 1-6:

chemical formula 1-1

Chemical formula 1-2

Chemical formulas 1 to 3

Chemical formulas 1 to 4

Chemical formulas 1 to 5

Chemical formulas 1 to 6

In the chemical formulas 1-1 to 1-6,

l1, L2, Y101 to Y103, Cy1, W, D, z and a to c are as defined in chemical formulae 1 and 2,

y104 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

d is an integer of 0 to 2,

when d is 2, 2Y 104 s are the same as or different from each other.

3. The organic light-emitting device according to claim 1, wherein the Cy1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms containing 1 or more O as a hetero element.

4. The organic light emitting device according to claim 1, wherein the chemical formula 1 is selected from the following compounds:

in the compound, the compound is a compound having a structure,

d is the deuterium, and the nitrogen is the hydrogen,

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

chemical formula A-1

In the chemical formula A-1, the metal oxide,

r1 to R3 and R1 to R3 are as defined in said formula A,

6. The organic light-emitting device according to claim 5, wherein the chemical formula a-1 satisfies 1 or more of (1) to (3):

(1) at least one of R1 to R3, R6, and R7 is a substituted or unsubstituted cycloalkyl group, or a group represented by the following chemical formula 2-a;

(2) at least one of R1 to R3, R6 and R7 is a group represented by the following chemical formula 2-B;

(3) 2 of adjacent R1, 2 of adjacent R2, 2 of adjacent R3, 2 of adjacent R6, or 2 of adjacent R7 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, or a substituted or unsubstituted aromatic heterocyclic ring,

in the chemical formulas 2-a and 2-B,

l11 is a direct bond or a substituted or unsubstituted arylene group,

p1 is 0 or 1 and,

y1 is C or Si,

at least one of T17 to T19 is a substituted or unsubstituted aryl group,

refers to the position of binding to formula a-1.

7. The organic light emitting device according to claim 1, wherein the chemical formula a is represented by the following chemical formula a-2 or a-3:

in the chemical formulas A-2 and A-3,

r1 to R3, R1 and R3 are as defined in formula A,

p2 to p4 are each 0 or 1,

r6 is an integer of 0 to 5,

8. The organic light emitting device according to claim 1, wherein 1 or more of the a1 and a2 are represented by the following chemical formula 2-C:

chemical formula 2-C

In the chemical formula 2-C,

is a position fused to formula a,

x is N (Ra1), O or S,

ra1 is a substituted or unsubstituted aryl group,

e1 is an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

9. The organic light-emitting device according to claim 1, wherein the chemical formula a is represented by any one of the following chemical formulae a-4 to a-7:

chemical formula A-4

Chemical formula A-5

Chemical formula A-6

Chemical formula A-7

In the chemical formulae A-4 to A-7,

r1, R3 to R5, R1 and R3 are as defined in formula A,

10. The organic light emitting device according to claim 1, wherein the chemical formula a is represented by the following chemical formula a-8:

chemical formula A-8

In the chemical formula A-8,

r3 to R5 and R3 are as defined in formula A,

x10 is C or Si,

11. The organic light emitting device according to claim 1, wherein 1 or more compounds among the compounds represented by chemical formula 1 and chemical formula a contain 1 or more deuterium.

12. The organic light emitting device of claim 5, wherein the formula a-1 is selected from the following compounds: