KR20210093753A - Polycyclic compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification provides a compound represented by chemical formula 1, and an organic light emitting device comprising the same. The compound described in the present specification can be used as a material for an organic material layer of the organic light emitting device. When the compound according to an embodiment of the present invention is applied to the organic light emitting device, it is possible to obtain the organic light emitting device having excellent luminous efficiency, low driving voltage, high efficiency, and long life by improving hole injection characteristics, electron injection and movement of the device.

Description

Polycyclic compound and organic light-emitting device comprising the same {POLYCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2020-0007424 filed with the Korean Intellectual Property Office on January 20, 2020, the entire contents of which are incorporated herein by reference.

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

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers, if necessary.

As materials used in organic light emitting devices, pure organic materials or complex compounds in which organic materials and metals are complexed account for most, and depending on the use, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. can be divided into Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state during oxidation, is mainly used. On the other hand, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state during reduction is mainly used. As the light emitting layer material, a material having both p-type properties and n-type properties, that is, a material having a stable form in both oxidation and reduction states is preferable, and excitons generated by recombination of holes and electrons in the light emitting layer are formed A material with high luminous efficiency that converts it into light when it is formed is preferable.

In order to improve the performance, lifespan or efficiency of an organic light emitting device, the development of a material for an organic thin film is continuously required.

Korean Patent Publication No. 10-2016-0132822

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

An exemplary embodiment of the present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 is a substituted or unsubstituted aryl group,

Ar2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a is an integer from 0 to 5, b is an integer from 0 to 7,

When a is 2 or more, two or more R1 are the same as or different from each other,

When b is 2 or more, two or more R2 are the same as or different from each other,

* is combined with the following formula (2),

[Formula 2]

In Formula 2,

X is O, S, NR, or CR'R";

R, R', R" and R3 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group;

c is an integer from 0 to 4,

when c is 2 or more, 2 or more R3 are the same as or different from each other,

* is a position combined with Formula 1 above.

Another embodiment of the present specification is a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one organic material layer among the organic material layers includes the compound.

The compound described herein may be used as a material for an organic material layer of an organic light emitting device. When the compound according to an exemplary embodiment of the present invention is applied to an organic light emitting device, hole injection characteristics and electron injection and movement of the device are improved, thereby providing an organic light emitting device having excellent luminous efficiency, low driving voltage, high efficiency and long life. can be obtained Specifically, since the compound described herein has an aryl (Ar1) bonded to the 2nd carbon position of the anthracene, it has a high HOMO (highest occupied molecular orbital) level to improve hole injection characteristics in the device, and the 9th position of the anthracene Since the substituent having excellent electron movement is bonded to the carbon position, electron injection and transport in the device can be improved.

1 to 3 illustrate an organic light emitting diode according to an exemplary embodiment of the present specification.

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

The present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 is a substituted or unsubstituted aryl group,

Ar2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a is an integer from 0 to 5, b is an integer from 0 to 7,

When a is 2 or more, two or more R1 are the same as or different from each other,

When b is 2 or more, two or more R2 are the same as or different from each other,

* is combined with the following formula (2),

[Formula 2]

In Formula 2,

X is O, S, NR, or CR'R";

R, R', R" and R3 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group;

c is an integer from 0 to 4,

when c is 2 or more, 2 or more R3 are the same as or different from each other,

* is a position combined with Formula 1 above.

The compound represented by Formula 1 includes a substituted or unsubstituted aryl group at the 2nd carbon position of anthracene, thereby increasing the HOMO energy level, thereby improving hole injection. In addition, since electron transfer is facilitated by including the substituent of Formula 2 condensed on dibenzofuran on carbon 9, the effect of improving electron injection is also exhibited. Therefore, when the compound of Formula 1 in which a specific substituent is bonded to the 2nd and 9th carbons of the anthracene is applied as a material for an organic light emitting device, both hole injection and electron injection effects are improved.

In the present specification, positions 2 and 9 of anthracene are as follows.

In the present specification, when a part "includes" a certain component, this means that other components may be further included rather than excluding other components unless otherwise stated.

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

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group (-CN); nitro group; hydroxyl group; carbonyl group; ester group; imid; amine group; silyl group; boron group; alkoxy group; an alkyl group; cycloalkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

As used herein, the term “substituted or unsubstituted” refers to deuterium; an alkyl group; And it means unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group.

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 include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but is not limited thereto .

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy and the like may be used, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; an alkylamine group; N-alkylarylamine group; arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 0 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group. , diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, and the like, but is not limited thereto.

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

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

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

In the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, and the N-alkylheteroarylamine group is the same as the examples of the alkyl group described above.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from examples of the heteroaryl group described below.

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the heteroaryl group described below.

In the present specification, the silyl group may be an alkylsilyl group or an arylsilyl group, and further may be a trialkylsilyl group or a triarylsilyl group. The number of carbon atoms of the silyl group is not particularly limited, but preferably 1 to 30, the alkylsilyl group may have 1 to 30 carbon atoms, and the arylsilyl group may have 6 to 30 carbon atoms. Specifically, there are trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc., but is not limited thereto. .

In the present specification, the boron group _{may be -BR 100} R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted C6-C30 aryl group; And it may be selected from the group consisting of a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, such as 6 to 30 carbon atoms, 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 preferably 6 to 60 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and 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. It is preferable that it is C10-60. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, phenalenyl group, perylenyl group, chrysenyl group, fluorenyl group, fluoranthenyl group, etc. , but is not limited thereto.

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

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

and

etc. can be However, the present invention is not limited thereto.

The description of the above-described aryl group may be cited except that the arylene group is divalent.

In the present specification, the heterocyclic group includes atoms other than carbon and one or more heteroelements, and specifically, the heterocyclic elements may include one or more atoms selected from the group consisting of O, N, S and P, etc. . The number of carbon atoms is not particularly limited, but preferably has 1 to 60 carbon atoms, more preferably 2 to 60 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. The heterocyclic group may be an aromatic ring, an aliphatic ring, or a ring condensed therewith. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, Triazolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolyl group, quinazolyl group, quinoxalyl group, phthalazinyl group, pyridopyrimidyl group, pyridopyrazinyl group, pyrazinopyrazinyl group group, isoquinolyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, phenanth rollinyl group (phenanthroline), isoxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but is not limited thereto.

The heteroaryl group refers to a monovalent aromatic heterocyclic group, and the heteroarylene group refers to a divalent aromatic heterocyclic group. The description of the above-mentioned heterocyclic group may be cited, except that the heteroaryl group and the heteroarylene group are aromatic.

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

According to an exemplary embodiment of the present specification, * in Formula 1 is combined with Formula 2 below. Specifically, two * in Formula 1 are bonded to two * in Formula 2 below, and the bonding direction is not limited.

[Formula 2]

In Formula 2,

X is O, S, NR, or CR'R";

R, R', R" and R3 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group;

c is an integer from 0 to 4,

when c is 2 or more, 2 or more R3 are the same as or different from each other,

* is a position combined with Formula 1 above.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

L1, L2, R1 to R3, Ar1, Ar2, X and a to c have the same definitions as in Formulas 1 and 2.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-8.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

[Formula 2-8]

In Formulas 2-1 to 2-8,

L1, L2, R1 to R3, Ar1, Ar2, X and a to c have the same definitions as in Formulas 1 and 2.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another exemplary embodiment, Ar1 is an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium.

According to another exemplary embodiment, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Ar1 is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.

According to another exemplary embodiment, Ar1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted phenanthryl group.

In another exemplary embodiment, Ar1 is a phenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; Or a phenanthryl group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted C 6 to C 60 aryl group; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In another exemplary embodiment, Ar2 is an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium; or a heteroaryl group having 2 to 60 carbon atoms that is unsubstituted or substituted with deuterium.

In another exemplary embodiment, Ar2 is a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In another exemplary embodiment, Ar2 is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium; or a heteroaryl group having 2 to 30 carbon atoms that is unsubstituted or substituted with deuterium.

In another exemplary embodiment, Ar2 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted formula 1-A.

[Formula 1-A]

In Formula 1-A,

Y is O, S, or NRa;

Ra is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

는 L2에 결합되는 위치를 의미한다.

denotes a position coupled to L2.

In another exemplary embodiment, Ar2 is a phenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; a phenanthryl group unsubstituted or substituted with deuterium; a fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group and an aryl group; a dibenzofuranyl group unsubstituted or substituted with deuterium; a dibenzothiophenyl group unsubstituted or substituted with deuterium; a carbazolyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and an aryl group; Or the following formula 1-A is unsubstituted or substituted with deuterium.

[Formula 1-A]

In Formula 1-A,

Y is O, S, or NRa;

Ra is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

는 L2에 결합되는 위치를 의미한다.

denotes a position coupled to L2.

In an exemplary embodiment of the present specification, "substituted or unsubstituted" in the definition of the substituent of Formula 1-A is deuterium; an alkyl group having 1 to 20 carbon atoms; an aryl group having 6 to 30 carbon atoms; And it means unsubstituted or substituted with one or more substituents selected from the group consisting of a heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ra is a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted C 6 to C 60 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, Ra is a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ra is a substituted or unsubstituted phenyl group.

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

In an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or an arylene group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium.

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

In an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or an arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.

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

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

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 30 alkyl group; or a substituted or unsubstituted C6-C60 aryl group.

In another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; an alkyl group having 1 to 30 carbon atoms that is unsubstituted or substituted with deuterium; or an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium.

According to another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently represent hydrogen or deuterium.

According to an exemplary embodiment of the present specification, a is an integer of 0 to 5, and when a is 2 or more, R1 of 2 or more are the same as or different from each other.

According to an exemplary embodiment of the present specification, b is an integer of 0 to 7, and when b is 2 or more, 2 or more R2 are the same as or different from each other.

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

According to another exemplary embodiment, X is O.

According to another exemplary embodiment, X is S.

According to another exemplary embodiment, X is NR.

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

According to an exemplary embodiment of the present specification, R, R', R" and R3 of Formula 2 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted C1-C30 alkyl group; or substituted or an unsubstituted C6-C60 aryl group.

According to another exemplary embodiment, R, R', R" and R3 are the same as or different from each other, and each independently hydrogen; deuterium; an alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; or deuterium It is a substituted or unsubstituted C6-C60 aryl group.

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

According to another exemplary embodiment, R is a substituted or unsubstituted phenyl group.

In another exemplary embodiment, R is a phenyl group.

According to an exemplary embodiment of the present specification, R' and R" are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 30 alkyl group; or a substituted or unsubstituted C 6 to C 30 aryl group am.

According to another exemplary embodiment, R' and R" are the same as or different from each other, and each independently represents a methyl group or a phenyl group.

In another exemplary embodiment, R' and R" are each a methyl group.

According to another exemplary embodiment, R' and R" are each a phenyl group.

In an exemplary embodiment of the present specification, R3 is hydrogen or deuterium.

According to an exemplary embodiment of the present specification, c in Formula 2 is an integer of 0 to 4, and when c is 2 or more, 2 or more R 3 are the same as or different from each other.

According to an exemplary embodiment of the present specification, in Formula 1, Ar2 is substituted with one or more deuterium.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 and Ar2 are each substituted with one or more deuterium.

According to an exemplary embodiment of the present specification, at least one deuterium is substituted in dibenzofuran in which anthracene, Ar2 and Formula 2 are condensed in Formula 1, respectively.

According to an exemplary embodiment of the present specification, at least one deuterium is substituted in dibenzofuran in which anthracene, Ar1, Ar2, and Formula 2 are condensed in Formula 1, respectively.

According to an exemplary embodiment of the present specification, the compound includes one or more deuterium. When the compound contains deuterium, the lifetime of the device is improved. Specifically, since the frequency of the carbon-deuterium bond becomes smaller than the frequency of the carbon-hydrogen bond, the stability of the compound including the carbon-deuterium bond is improved.

In an exemplary embodiment of the present specification, the deuterium substitution rate of the compound is 10% to 100%.

In the present specification, the deuterium substitution ratio means a substitution ratio of deuterium in a molecule, and can be confirmed through a known method. As an example, the determination of the substitution distribution of deuterium in a molecule follows the following method. The following TLC-MS is a method for controlling the substitution ratio of deuterium in the synthesis process of the compound.

1. TLC-MS (Thin-Layer Chromatography/Mass Spectrometry) is used (synthesis process confirmation method)

The substitution rate can be calculated based on the maximum value (max. value) of the distribution of molecular weights at the end of the reaction.

In an exemplary embodiment of the present specification, Chemical Formula 1 is selected from the following compounds.

The present specification provides an organic light emitting device including the above-described compound.

An exemplary embodiment of the present specification includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers provides an organic light emitting device including the compound represented by Formula 1 .

The organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described compound.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention is an organic material layer, a hole injection layer, a hole transport layer, a layer that transports and injects holes at the same time, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer that performs both electron transport and electron injection. It may have a structure including the like. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material layers.

In an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

In an exemplary embodiment of the present specification, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.

In an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound.

In an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound as a host of the emission layer.

In an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes the above-described compound as a host of the light emitting layer, and may further include a dopant.

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

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

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

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 such a structure, the compound may be included in the light emitting layer 3 .

2 shows 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 The structure is illustrated. In such a structure, the compound may be included in the hole injection layer 5 , the hole transport layer 6 , the light emitting layer 7 or the electron transport layer 8 .

3, the anode 2, the hole injection layer 5, the hole transport layer 6, the light emitting layer 7, the electron transport layer 8, the electron injection layer 9 and the cathode 4 are sequentially on the substrate 1 The structure of the organic light emitting device stacked with In such a structure, the compound may be included in the hole injection layer 5 , the hole transport layer 6 , the light emitting layer 7 or the electron transport layer 8 .

For example, the organic light emitting device of the present specification uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or a conductive metal oxide or an alloy thereof on a substrate. After forming an anode by vapor deposition, and forming an organic material 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 thereon, a material that can be used as a cathode is deposited thereon. can In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a layer that simultaneously injects and transports electrons, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously injects and transports electrons, etc. However, the present invention is not limited thereto and may have a single layer structure. In addition, the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

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

The cathode is an electrode for injecting electrons, and the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer. As the hole injection material, holes can be well injected from the anode at a low voltage, and the hole injection material has the highest occupied (HOMO). The molecular orbital) is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, and conductive polymers of polyaniline and polythiophene series, but are not limited thereto.

The hole transport layer may serve to facilitate hole transport. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

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

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene; Rubrene and the like, but is not limited thereto.

In an exemplary embodiment of the present specification, the light emitting layer may include the compound as a host, and may include an additional host in addition to the compound.

The additional host material may include a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type compounds. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

As the luminescent dopant, PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum) A phosphorescent material such as , Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. When the emission layer emits green light, a _{phosphor such as Ir(ppy) 3} (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, the present invention is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant is a _{phosphor such as (4,6-F 2} ppy) ₂ Irpic, or spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA). ), a PFO-based polymer, a fluorescent material such as a PPV-based polymer may be used, but is not limited thereto.

In one embodiment of the present specification, a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used for the hole blocking layer.

The electron transport layer may serve to facilitate the transport of electrons. As the electron transport material, a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer is suitable. Specific examples include Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto.

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

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

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

Hereinafter, the present specification will be described in more detail through examples. However, the following examples are only for illustrating the present specification, and not for limiting the present specification.

<Synthesis example>

Synthesis Example 1. Synthesis of Intermediate 1

Synthesis Example 1-1. Synthesis of compound 1-a

2-Bromo-1-fluorodibenzo[b,d]furan (80g, 302mmol) and (5-chloro-2-hydroxyphenyl)boronic acid (52.0g, 302mml) were mixed with tetrahydrofuran (THF, 1500ml) After dissolving in Pd(PPh ₃ ) ₄ (6.97 g, 6.0 mmol) and _{300 ml of 2M K 2} CO ₃ aqueous solution were added and 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 purified by column chromatography to obtain compound 1-a (63 g, yield 67%).

Synthesis Example 1-2. Synthesis of compound 1-b

Compound 1-a (63g, 201mmol) was dissolved in dimethylformamide (DMF, 1000ml), K ₂ CO ₃ (83.5g, 604mmol) was added, and the mixture was stirred under reflux for 2 hours. After cooling the reaction solution, it was poured into 3L of distilled water to form a solid. After filtering the solid, it was 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 purified using column chromatography to obtain compound 1-b (46 g, 78%).

Synthesis Example 1-3. Synthesis of Intermediate 1

Compound 1-b (46g, 157mmol), bis(pinacolato)diboron (48g, 189mmol), and potassium acetate (KOAc) (31g, 314mmol) were put together with 400ml of dioxane in a flask and dispersed. Bis (dibenzylideneacetone) palladium (0) (Pd(dba) ₂ ) (1.81g, 3.1mmol), tricyclohexylphosphine (PCy ₃ ) (1.76g, 6.3mmol) was added and refluxed for 24 hours. stirred. After completion of the reaction, dioxane was removed by distillation under reduced pressure. After dissolving in chloroform and extracting with distilled water three times, the organic layer was distilled under reduced pressure to remove chloroform. Intermediate 1 was obtained by purification using column chromatography. (42g, yield 70%)

Synthesis Example 2. Synthesis of Intermediate 2

Synthesis Example 2-1. Synthesis of compound 2-a

Compound 2-a was obtained in the same manner in Synthesis Example 1-1 using 3-bromo-4-fluorodibenzo[b,d]furan and (5-chloro-2-hydroxyphenyl)boronic acid.

Synthesis Example 2-2. Synthesis of compound 2-b

Compound 2-b was obtained in the same manner using compound 2-a in Synthesis Example 1-2.

Synthesis Example 2-3. Synthesis of Intermediate 2

Intermediate 2 was obtained in the same manner using compound 2-b in Synthesis Example 1-3.

Synthesis Example 3. Synthesis of Intermediate 3

Synthesis Example 3-1. Synthesis of compound 3-a

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

Synthesis Example 3-2. Synthesis of compound 3-b

Compound 3-b was obtained in the same manner using compound 3-a in Synthesis Example 1-2.

Synthesis Example 3-3. Synthesis of Intermediate 3

Intermediate 3 was obtained in the same manner using compound 3-b in Synthesis Example 1-3.

Synthesis Example 4. Synthesis of Intermediate 4

Synthesis Example 4-1. Synthesis of compound 4-a

Compound 4-a was obtained in the same manner in Synthesis Example 1-1 using 3-bromo-4-fluorodibenzo[b,d]furan and (2-chloro-6-hydroxyphenyl)boronic acid.

Synthesis Example 4-2. Synthesis of compound 4-b

Compound 4-b was obtained in the same manner using compound 4-a in Synthesis Example 1-2.

Synthesis Example 4-3. Synthesis of Intermediate 4

Intermediate 4 was obtained in the same manner using compound 4-b in Synthesis Example 1-3.

Synthesis Example 5. Synthesis of Intermediate 5

Synthesis Example 5-1. Synthesis of compound 5-a

Compound 5-a was obtained in the same manner as in Synthesis Example 1-1 using 2-bromo-1-fluorodibenzo[b,d]furan and (4-chloro-2-hydroxyphenyl)boronic acid.

Synthesis Example 5-2. Synthesis of compound 5-b

Compound 5-b was obtained in the same manner using compound 5-a in Synthesis Example 1-2.

Synthesis Example 5-3. Synthesis of Intermediate 5

Intermediate 5 was obtained in the same manner using compound 5-b in Synthesis Example 1-3.

Synthesis Example 6. Synthesis of Intermediate 6

Synthesis Example 6-1. Synthesis of compound 6-a

Dibenzo[b,d]thiophen-1-ol (100g, 499mmol) was dissolved in DMF (2000ml), and then N-bromosuccinimide (89g, 499mmol) dissolved in DMF 500ml was slowly added dropwise. After stirring at room temperature for 2 hours, 3000 ml of water was added dropwise. When a solid was formed, it was dissolved in chloroform after filtering and extracted several times with distilled water. The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. Compound 6-a was obtained by purification through column chromatography. (65 g, yield 65%)

Synthesis Example 6-2. Synthesis of compound 6-b

In Synthesis Example 1-1, compound 6-b was obtained in the same manner using compound 6-a and (5-chloro-2-fluorophenyl)boronic acid.

Synthesis Example 6-3. Synthesis of compound 6-c

Compound 6-c was obtained in the same manner using compound 6-b in Synthesis Example 1-2.

Synthesis Example 6-4. Synthesis of Intermediate 6

Intermediate 6 was obtained in the same manner using compound 6-c in Synthesis Example 1-3.

Synthesis Example 7. Synthesis of Intermediate 7

Synthesis Example 7-1. Synthesis of compound 7-a

After dissolving 2-bromo-4-chloro-1-fluorobenzene (100 g, 477 mmol) and (2-hydroxyphenyl) boronic acid (66 g, 477 mmol) in THF (1500 ml), Pd (PPh ₃ ) ₄ ( 11 g, 9.5 mmol) and _{300 ml of 2M K 2} CO ₃ aqueous solution were added and 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 purified using column chromatography to obtain compound 7-a (72 g, yield 68%).

Synthesis Example 7-2. Synthesis of compound 7-b

Compound 7-a (72 g, 323 mmol) was dissolved in 1000 ml of DMF, and then N-bromosuccinimide (57.6 g, 323 mmol) dissolved in 100 ml of DMF was slowly added dropwise. After stirring at room temperature for 2 hours, 2000 ml of water was added dropwise. When a solid was formed, it was dissolved in chloroform after filtering and extracted several times with distilled water. After removing moisture from the organic layer with anhydrous magnesium sulfate, the solvent was removed by distillation under reduced pressure. Purification by column chromatography gave compound 7-b. (65 g, yield 67%)

Synthesis Example 7-3. Synthesis of compound 7-c

Compound 7-b (65g, 216mmol) was dissolved in DMF (1000ml), K ₂ CO ₃ (89g, 647mmol) was added, and the mixture was stirred under reflux for 2 hours. After cooling the reaction solution, it was poured into 3L of distilled water to form a solid. After filtering the solid, it was 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 purified by column chromatography to obtain compound 7-c (39 g, 64%).

Synthesis Example 7-4. Synthesis of compound 7-d

Compound 7-c (39g, 138mmol) and (2-(methoxycarbonyl)phenyl)boronic acid (25g, 138moml) were dissolved in THF (500ml), and then Pd(PPh ₃ ) ₄ (3.2 g, 2.7 mmol) and 100 ml of 2M K ₂ CO ₃ aqueous solution were added and 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 purified using column chromatography to obtain compound 7-d (30 g, yield 64%).

Synthesis Example 7-5. Synthesis of compound 7-e

Compound 7-d (30 g, 89 mmol) was dissolved in 450 ml of THF. After the temperature was lowered to 0° C. under a nitrogen atmosphere, _{89 ml of 3 M CH 3} MgBr was slowly added dropwise. The temperature was gradually raised to room temperature. After stirring for 1 hour, the temperature was raised and the mixture was stirred under reflux for 12 hours. After cooling the reaction solution, quenching with HCl solution, THF was distilled under reduced pressure. Ethyl acetate (EA) and water were added for extraction. EA was removed under reduced pressure and purified using column chromatography to obtain compound 7-e (22 g, yield 73%).

Synthesis Example 7-6. Synthesis of compound 7-f

Compound 7-e (22 g, 65 mmol) was dispersed in 250 ml of acetic acid and 1.1 ml of hydrochloric acid, followed by stirring under reflux for 24 hours. The precipitated solid was filtered and washed with water. It was dissolved in ethyl acetate (EA) and extracted several times with water. The organic layer was distilled under reduced pressure and purified using column chromatography to obtain compound 7-f (12 g, yield 57%).

Synthesis Example 7-7. Synthesis of Intermediate 7

Intermediate 7 was obtained in the same manner using compound 7-f in Synthesis Example 1-3.

Synthesis Example 8. Synthesis of Intermediate 8

Synthesis Example 8-1. Synthesis of compound 8-a

After dissolving 1-bromo-2-fluoro-3-iodobenzene (100 g, 332 mmol) and (2-chloro-6-hydroxyphenyl) boronic acid (57.3 g, 332 mmol) in THF (1500 ml), Pd (PPh ₃ ) ₄ (7.68 g, 6.6 mmol) and _{300 ml of 2M Na 2} CO ₃ aqueous solution were added and 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 purified by column chromatography to obtain compound 8-a (69 g, yield 69%).

Synthesis Example 8-2. Synthesis of compound 8-b

Compound 8-a (69g, 229mmol) was dissolved in DMF (1000ml), K ₂ CO ₃ (95g, 686mmol) was added, and the mixture was stirred under reflux for 2 hours. After cooling the reaction solution, it was poured into 3L of distilled water to form a solid. After filtering the solid, it was 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 purified by column chromatography to obtain compound 8-b (44 g, 68%).

Synthesis Example 8-3. Synthesis of compound 8-c

Compound 8-b (44g, 156mmol) and (2-nitrophenyl)boronic acid (26g, 156mml) were dissolved in THF (800ml), and then Pd(PPh ₃ ) ₄ (3.61 g, 3.1mmol) and 2M K ₂ CO ₃ 200ml of aqueous solution was added and 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 purified using column chromatography to obtain compound 8-c (39 g, yield 77%).

Synthesis Example 8-4. Synthesis of compound 8-d

Compound 8-c (39g, 120mmol) and PPh ₃ (79g, 301mmol) were dissolved in 600ml of o-dichlorobenzene and stirred under reflux for 8 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, dissolved in chloroform, and extracted several times with distilled water. The organic layer was taken, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove chloroform. Purification using column chromatography gave compound 8-d (21 g, 60%).

Synthesis Example 8-5. Synthesis of compound 8-e

Compound 8-d (21g, 72mmol) and iodobenzene (14.7g, 72mml) were dissolved in 250ml of DMF, and then CS ₂ CO ₃ (46.9g, 144mmol) and CuI (2.74g, 14mmol) were added. After raising the temperature to 120 °C, the mixture was stirred for 16 hours. After cooling the reaction solution, 1 L of ethyl acetate was added thereto, transferred to a separatory funnel, and extracted once with aqueous ammonia and extracted 3 times with 1 L of distilled water. The organic layers were collected, treated with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. Compound 8-e was obtained by purification using column chromatography. (15 g, yield 57%)

Synthesis Example 8-6. Synthesis of Intermediate 8

Intermediate 8 was obtained in the same manner using compound 8-e in Synthesis Example 1-3.

Synthesis Example 9. Synthesis of Intermediate 9

Synthesis Example 9-1. Synthesis of compound 9-a

In Synthesis Example 8-1, compound 9-a was obtained in the same manner using 4-bromo-2-fluoro-1-iodobenzene.

Synthesis Example 9-2. Synthesis of compound 9-b

Compound 9-b was obtained in the same manner using compound 9-a in Synthesis Example 8-2.

Synthesis Example 9-3. Synthesis of compound 9-c

Compound 9-c was obtained in the same manner using compound 9-b in Synthesis Example 8-3.

Synthesis Example 9-4. Synthesis of compound 9-d

Compound 9-d was obtained in the same manner using compound 9-c in Synthesis Example 8-4.

Synthesis Example 9-5. Synthesis of compound 9-e

Compound 9-e was obtained in the same manner using compound 9-d in Synthesis Example 8-5.

Synthesis Example 9-6. Synthesis of Intermediate 9

Intermediate 9 was obtained in the same manner using compound 9-e in Synthesis Example 1-3.

Synthesis Example 10. Synthesis of compound BH-A

Synthesis Example 10-1. Synthesis of compound 10-a

After dissolving 2-bromoanthracene (100 g, 389 mmol) and 1-naphthaleneboronic acid (66.9 g, 389 mmol) in THF (2000 ml), Pd(PPh ₃ ) ₄ (9.0 g, 7.8 mmol) and 2M K ₂ CO ₃ 400 ml of aqueous solution was added and 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 purified by column chromatography to obtain compound 10-a (94 g, yield 80%).

Synthesis Example 10-2. Synthesis of compound 10-b

Compound 10-a (94 g, 311 mmol) was dissolved in 1200 ml of DMF, and then N-bromosuccinimide (55.3 g, 311 mmol) dissolved in 300 ml of DMF was slowly added dropwise. After stirring at room temperature for 2 hours, 3000 ml of water was added dropwise. When a solid was formed, it was dissolved in chloroform after filtering and extracted several times with distilled water. Recrystallization from ethyl acetate gave compound 10-b. (73 g, yield 61%)

Synthesis Example 10-3. Synthesis of compound 10-c

After dissolving compound 10-b (73 g, 189 mmol) and Intermediate 1 (72.6 g, 189 mmol) in Dioxane (1000 ml), Pd(PPh ₃ ) ₄ (4.4 g, 3.8 mmol) and 2M K ₂ CO ₃ aqueous solution 200 ml and 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 purified using column chromatography to obtain compound 10-c (52 g, yield 72%).

Synthesis Example 10-4. Synthesis of compound 10-d

Compound 10-c (52 g, 136 mmol) was dissolved in 600 ml of DMF, and then N-bromosuccinimide (24.2 g, 136 mmol) dissolved in 100 ml of DMF was slowly added dropwise. After stirring at room temperature for 2 hours, 1500 ml of water was added dropwise. When a solid was formed, it was dissolved in chloroform after filtering and extracted several times with distilled water. Recrystallization from ethyl acetate gave compound 10-d. (41 g, yield 66%)

Synthesis Example 10-5. Synthesis of BH-A

Compound 10-d (41 g, 64 mmol) and phenylboronic acid (7.8 g, 64 mmol) were dissolved in THF (500 ml), followed by Pd(PPh ₃ ) ₄ (1.5 g, 1.3 mmol) and 2M K ₂ CO ₃ 100 ml of aqueous solution was added and 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 purified using column chromatography to obtain compound BH-A (32 g, yield 78%). The final compound was identified as a mass value. [cal. m/s: 636.7, exp. m/s (M+H) 637.7]

Synthesis Example 11. Synthesis of compound BH-B

In Synthesis Example 10, using 1-naphthaleneboronic acid instead of phenylboronic acid, BH-B was obtained in the same manner. The final compound was identified as a mass value. [cal. m/s: 686.8, exp. m/s (M+H) 687.8]

Synthesis Example 12. Synthesis of compound BH-C

In Synthesis Example 10, BH-C was obtained in the same manner by using Intermediate 2 instead of Intermediate 1 and 2-naphthaleneboronic acid instead of phenylboronic acid. The final compound was identified as a mass value. [cal. m/s: 686.8, exp. m/s (M+H) 687.8]

Synthesis Example 13. Synthesis of compound BH-D

In Synthesis Example 10, BH-D was obtained in the same manner by using Intermediate 2 instead of Intermediate 1 and 9-phenanthryl boronic acid instead of phenylboronic acid. The final compound was identified as a mass value. [cal. m/s: 736.9, exp. m/s (M+H) 737.9]

Synthesis Example 14. Synthesis of compound BH-E

In Synthesis Example 10, using Intermediate 3 instead of Intermediate 1, BH-E was obtained in the same manner. The final compound was identified as a mass value. [cal. m/s: 636.7, exp. m/s (M+H) 637.7]

Synthesis Example 15. Synthesis of compound BH-F

In Synthesis Example 10, BH-F was obtained in the same manner by using Intermediate 3 instead of Intermediate 1 and 1-naphthaleneboronic acid instead of phenylboronic acid. The final compound was identified as a mass value. [cal. m/s: 686.8, exp. m/s (M+H) 687.8]

Synthesis Example 16. Synthesis of compound BH-G

In Synthesis Example 10, BH-G was obtained in the same manner by using Intermediate 3 instead of Intermediate 1 and 2-naphthaleneboronic acid instead of phenylboronic acid. The final compound was identified as a mass value. [cal. m/s: 686.8, exp. m/s (M+H) 687.8]

Synthesis Example 17. Synthesis of compound BH-H

In Synthesis Example 10, using 9-phenanthryl boronic acid instead of 1-naphthalene boronic acid and Intermediate 3 instead of Intermediate 1, BH-H was obtained in the same manner. The final compound was identified as a mass value. [cal. m/s: 686.8, exp. m/s (M+) 687.8]

Synthesis Example 18. Synthesis of compound BH-I

In Synthesis Example 10, using phenylboronic acid instead of 1-naphthaleneboronic acid and Intermediate 2 instead of Intermediate 1, BH-I was obtained in the same manner. The final compound was identified as a mass value. [cal. m/s: 586.7, exp. m/s (M+H) 587.7]

Synthesis Example 19. Synthesis of compound BH-J

In Synthesis Example 10, using phenylboronic acid instead of 1-naphthaleneboronic acid and Intermediate 4 instead of Intermediate 1, BH-J was obtained in the same manner. The final compound was identified as a mass value. [cal. m/s: 586.7, exp. m/s (M+H) 587.7]

Synthesis Example 20. Synthesis of compound BH-K

In Synthesis Example 10, using phenylboronic acid instead of 1-naphthaleneboronic acid and Intermediate 5 instead of Intermediate 1, BH-K was obtained in the same manner. The final compound was identified as a mass value. [cal. m/s: 586.7, exp. m/s (M+H) 587.7]

Synthesis Example 21. Synthesis of Intermediate 11

Synthesis Example 21-1. Synthesis of compound 11-a

Compound 11-a was synthesized in the same manner as in Synthesis Example 1-1 using 1-bromo-4-chlorobenzene.

Synthesis Example 21-2. Synthesis of Intermediate 11

Intermediate 11 was synthesized in the same manner using compound 11-a in Synthesis Example 1-3.

Synthesis Example 22. Synthesis of compound BH-L

In Synthesis Example 10, BH-L was obtained in the same manner by using Intermediate 11 instead of Intermediate 1. The final compound was identified as a mass value. [cal. m/s: 712.8, exp. m/s (M+H) 713.8]

Synthesis Example 23. Synthesis of compound BH-M

In Synthesis Example 10, using Intermediate 6 instead of Intermediate 1, BH-M was obtained in the same manner. The final compound was identified as a mass value. [cal. m/s: 652.8, exp. m/s (M+H) 653.8]

Synthesis Example 24. Synthesis of compound BH-N

In Synthesis Example 10, using Intermediate 7 instead of Intermediate 1, BH-N was obtained in the same manner. The final compound was identified as a mass value. [cal. m/s: 662.8, exp. m/s (M+H) 663.8]

Synthesis Example 25. Synthesis of compound BH-O

In Synthesis Example 10, using Intermediate 8 instead of Intermediate 1, BH-O was obtained in the same manner. The final compound was identified as a mass value. [cal. m/s: 711.9, exp. m/s (M+H) 712.9]

Synthesis Example 26. Synthesis of compound BH-P

In Synthesis Example 10, using Intermediate 9 instead of Intermediate 1, BH-P was obtained in the same manner. The final compound was identified as a mass value. [cal. m/s: 711.9, exp. m/s (M+H) 712.9]

Synthesis Example 27. Synthesis of compound BH-Q

BH-A (20g) and AlCl ₃ (4g) were added to C ₆ D ₆ (600ml) and stirred for 2 hours. After completion of the reaction, D ₂ O (30ml) was added, stirred for 30 minutes, and then trimethylamine (2.4ml) was added dropwise. The reaction solution was transferred to a separatory funnel, and extracted with water and toluene. The extract _{was dried over MgSO 4} , and recrystallized from ethyl acetate to obtain BH-Q. (15 g, yield 75%) The final compound was confirmed as a mass value. Compounds substituted with deuterium have a molecular weight distribution. [cal. m/s: 664.9, exp. m/s (M+H) 658 ~ 665]

Synthesis Example 28. Synthesis of Intermediate 12

Intermediate 12 was obtained in the same manner as in Synthesis Example 27 using 2-chloroanthracene. The final compound was identified as a mass value. Compounds substituted with deuterium have a molecular weight distribution. [cal. m/s: 221.7, exp. m/s (M+H) 220 ~ 222]

Synthesis Example 29. Synthesis of compound BH-R

In Synthesis Example 10, BH-R was obtained in the same manner by using Intermediate 12 instead of 2-bromoanthracene. The final compound was identified as a mass value. [cal. m/s: 643.8, exp. m/s (M+H) 642 to 644]

Synthesis Example 30. Synthesis of compound BH-S

BH-S was obtained in the same manner using BH-J in Synthesis Example 27. The final compound was identified as a mass value. Compounds substituted with deuterium have a molecular weight distribution. [cal. m/s: 612.8, exp. m/s (M+H) 607 ~ 613]

Synthesis Example 31. Synthesis of compound BH-T

In Synthesis Example 10, BH-T was obtained in the same manner using Intermediate 12 instead of 2-bromoanthracene, Intermediate 4 instead of Compound 1, and phenylboronic acid instead of 1-naphthaleneboronic acid. The final compound was identified as a mass value. [cal. m/s: 593.7, exp. m/s (M+H) 592 to 594]

<Experimental example>

Example 1. Manufacture of an organic light emitting device

A glass substrate coated with indium tin oxide (ITO) to a thickness of 150 nm was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. In this case, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using nitrogen plasma, the substrate was transported to a vacuum evaporator. A hole injection layer was formed by thermal vacuum deposition of the HAT-CN compound to a thickness of 5 nm on the prepared ITO transparent electrode. Then, HTL1 was thermally vacuum deposited to a thickness of 100 nm, and then HTL2 was thermally vacuum deposited to a thickness of 10 nm to form a hole transport layer. Then, compound BH-A as a host and BD-A (weight ratio 97:3) as a dopant were simultaneously vacuum-deposited to form a light emitting layer with a thickness of 20 nm. Then, ETL was vacuum-deposited to a thickness of 20 nm to form an electron transport layer. Then, LiF was vacuum-deposited to a thickness of 0.5 nm to form an electron injection layer. Then, aluminum was deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic light emitting diode.

The structures of the compounds used in the Examples are as follows.

Examples 2 to 20 and Comparative Examples 1 to 3.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of the compound BH-A as a host of the light emitting layer in Example 1.

In the organic light emitting diodes prepared in Examples 1 to 20 and Comparative Examples 1 to 3, the driving voltage and luminous efficiency were measured at a current density of ^{10 mA/cm 2} , and initial luminance at a current density of ^{20 mA/cm 2} By measuring the time (LT) to be 95% of the contrast, the results are shown in Table 1 below.

compound 10 mA/cm ² measured value LT (T95%) (light emitting layer host) Driving voltage (Vop) Luminous Efficiency (Cd/A) Example 1 BH-A 3.60 7.01 152 Example 2 BH-B 3.66 7.04 157 Example 3 BH-C 3.62 7.22 159 Example 4 BH-D 3.62 7.32 142 Example 5 BH-E 3.41 6.88 133 Example 6 BH-F 3.48 7.01 127 Example 7 BH-G 3.45 6.81 161 Example 8 BH-H 3.50 7.01 146 Example 9 BH-I 3.63 7.18 173 Example 10 BH-J 3.45 6.95 187 Example 11 BH-K 3.68 6.98 153 Example 12 BH-L 3.49 7.05 146 Example 13 BH-M 3.63 7.15 123 Example 14 BH-N 3.64 7.20 127 Example 15 BH-O 3.55 7.00 123 Example 16 BH-P 3.45 6.88 126 Example 17 BH-Q 3.60 7.01 273 Example 18 BH-R 3.60 7.01 300 Example 19 BH-S 3.45 6.99 260 Example 20 BH-T 3.45 6.87 286 Comparative Example 1 BH-1 3.98 6.34 94 Comparative Example 2 BH-2 3.68 6.33 110 Comparative Example 3 BH-3 3.33 4.12 20

Examples 1 to 20 using the compound represented by Chemical Formula 1 of the present invention showed characteristics of low voltage and high efficiency as compared to Comparative Examples 1 to 3, and exhibited excellent lifespan. In addition, from Examples 17 to 20, it was confirmed that the lifespan of the device using the deuterium-substituted compound was significantly improved.

In Comparative Example 1, compound BH-1 in which Ar1 of Formula 1 is hydrogen was used, and it was confirmed that the driving voltage was higher and the efficiency and lifespan were lower than in Examples 1 to 20. In addition, the compound BH-2 used in Comparative Example 2 corresponds to a case in which Ar1 is hydrogen or aryl is substituted at the 3rd position of anthracene in Formula 1, and a decrease in driving voltage is seen compared to Comparative Example 1, but lower efficiency and showed a short lifespan.

Compound BH-3 used in Comparative Example 3 has a structure in which a heterocycle not containing O is bonded to a 5-ring condensed heterocyclic position containing O in Formula 1, and has the most electronegativity among N, S and O Since large O is not included, injection of electrons is not easier than in the present embodiment, and it can be seen that the efficiency and lifespan of the device are reduced. In addition, the compound BH-3 has a structure in which aryl is simultaneously substituted at positions 2 and 6 of anthracene, and in this case, the conjugate length of the molecule is too long to have an energy gap similar to that of the dopant, and the driving voltage is lowered energy transfer becomes difficult. Therefore, it can be confirmed that substitution of only Ar1 leads to improvement in driving voltage, efficiency, and lifespan.

1: substrate
2: Anode
3: light emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: light emitting layer
8: electron transport layer
9: electron injection layer

Claims (14)

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

In Formula 1,
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 is a substituted or unsubstituted aryl group,
Ar2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
a is an integer from 0 to 5, b is an integer from 0 to 7,
When a is 2 or more, two or more R1 are the same as or different from each other,
When b is 2 or more, two or more R2 are the same as or different from each other,
* is combined with the following formula (2),
[Formula 2]

In Formula 2,
X is O, S, NR, or CR'R";
R, R', R" and R3 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group;
c is an integer from 0 to 4,
when c is 2 or more, 2 or more R3 are the same as or different from each other,
* is a position combined with Formula 1 above. The method according to claim 1, wherein Formula 1 is a compound represented by Formula 1-1 or 1-2 below:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,
L1, L2, R1 to R3, Ar1, Ar2, X and a to c have the same definitions as in Formulas 1 and 2. The compound according to claim 1, wherein Ar1 is a substituted or unsubstituted C6-C60 aryl group. The method according to claim 1, wherein L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group. The method according to claim 1, wherein Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a compound that is a substituted or unsubstituted C 2 to C 60 heteroaryl group. The compound of claim 1 , wherein the compound comprises at least one deuterium. The compound according to claim 1, wherein the compound has a deuterium substitution rate of 10% to 100%. The compound according to claim 1, wherein Formula 1 is selected from the following compounds:

. a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound according to any one of claims 1 to 8. . The organic light emitting diode of claim 9 , wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound. The organic light-emitting device of claim 9 , wherein the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound. The organic light emitting device of claim 9 , wherein the organic material layer includes an emission layer, and the emission layer includes the compound. The organic light emitting device of claim 9 , wherein the organic material layer includes an emission layer, and the emission layer includes the compound as a host of the emission layer. The organic light emitting diode of claim 13 , wherein the light emitting layer further comprises a dopant.

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