KR102605832B1 - Compound and organic light emitting device comprising same - Google Patents

Abstract

This specification provides a compound of Formula 1 and an organic light-emitting device containing the same.

Description

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

This specification claims the benefit of Korean Patent Application No. 10-2020-0007436 filed with the Korean Intellectual Property Office on January 20, 2020, the entire contents of which are included in this specification.

This specification relates to compounds and organic light-emitting devices containing the same.

Organic light emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting device with this structure, electrons and holes injected from two electrodes combine in the organic thin film to form a pair and then annihilate, emitting light. The organic thin film may be composed of a single layer or multiple layers as needed.

Most of the materials used in organic light-emitting devices are pure organic materials or complexes of organic materials and metals. Depending on the application, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. It can be divided into: Here, organic materials with p-type properties, that is, organic materials that are easily oxidized and have an electrochemically stable state upon oxidation, are mainly used as hole injection materials or hole transport materials. Meanwhile, organic materials with n-type properties, that is, organic materials that are easily reduced and have an electrochemically stable state upon reduction, are mainly used as electron injection materials or electron transport materials. The emitting layer material is preferably a material that has both p-type and n-type properties, that is, a material that is stable in both oxidation and reduction states, and excitons are formed when holes and electrons recombine in the emitting layer. A material with high luminous efficiency that converts light into light is desirable.

In order to improve the performance, lifespan, or efficiency of organic light-emitting devices, the development of organic thin film materials is continuously required.

Korean Patent Publication No. 2016-132822

This specification provides a compound and an organic light-emitting device containing 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 or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

Either Az1 or Az2 is -L10-Ar1, and the other is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

L1, L2 and L10 are the same or different from each other and are each independently directly bonded; 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 heterocyclic group,

a is an integer from 0 to 5, b is an integer from 0 to 6,

When a is 2 or more, 2 or more R1s are the same or different from each other,

When b is 2 or more, 2 or more R2s are the same or different from each other,

* combines with Formula 2 below,

[Formula 2]

In Formula 2,

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

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

c is an integer from 0 to 4,

When c is 2 or more, 2 or more R3s are the same or different from each other,

* is the position bonded to Formula 1 above.

Another embodiment of the present specification includes a first electrode; a second electrode provided opposite the first electrode; and an organic light emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound.

The compounds described in this specification can be used as a material for the organic layer of an organic light-emitting device. When the compound according to an embodiment of the present invention is applied to an organic light emitting device, the hole injection characteristics and electron injection and movement of the device are improved, resulting in an organic light emitting device having excellent luminous efficiency, low driving voltage, high efficiency, and long lifespan. You can get it. Specifically, the compound described in this specification has an aryl (Ar1) bonded to the 2nd or 3rd carbon position of anthracene, so it has a high HOMO (highest occupied molecular orbital) level and can improve hole injection characteristics in the device. Since a substituent with excellent electron mobility is attached to the 9th carbon position, electron injection and transport within the device can be improved.

1 to 3 show an organic light emitting device according to an exemplary embodiment of the present specification.

Hereinafter, this specification will be described in more detail.

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

[Formula 1]

In Formula 1,

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

Either Az1 or Az2 is -L10-Ar1, and the other is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

L1, L2 and L10 are the same or different from each other and are each independently directly bonded; 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 heterocyclic group,

a is an integer from 0 to 5, b is an integer from 0 to 6,

When a is 2 or more, 2 or more R1s are the same or different from each other,

When b is 2 or more, 2 or more R2s are the same or different from each other,

* combines with Formula 2 below,

[Formula 2]

In Formula 2,

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

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

c is an integer from 0 to 4,

When c is 2 or more, 2 or more R3s are the same or different from each other,

* is the position bonded to Formula 1 above.

The compound represented by Formula 1 contains a substituted or unsubstituted aryl group at the 2nd or 3rd carbon position of anthracene, thereby increasing the HOMO energy level and improving hole injection. In addition, by including the substituent in which the formula 2 is condensed in the dibenzofuran at position 9, electron transfer is facilitated, which also has the effect of improving electron injection. Therefore, when the compound represented by Formula 1 is applied as a host of an organic light emitting device, both hole injection and electron injection effects are improved.

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

In this specification, when a part “includes” a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.

Examples of substituents in this 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 changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same 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; imide group; Amine group; silyl group; boron group; Alkoxy group; Alkyl group; Cycloalkyl group; Aryl group; and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent. For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

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

As used herein, “substituted or unsubstituted” refers to deuterium; an alkyl group having 1 to 20 carbon atoms; Aryl group having 6 to 30 carbon atoms; and substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups having 2 to 30 carbon atoms.

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

In the present specification, the alkyl group may be straight chain 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- Examples include, but are not limited to, 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, and 1-methylhexyl group.

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

In the present specification, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. 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, etc., but is not limited thereto.

In this specification, the amine group is -NH ₂ ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine group and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 0 to 30. Specific examples of amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthrylamine group, and 9-methyl-anthrylamine group. , diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N- Biphenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrylamine group, N-biphenylphenanthrylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group , N-phenanthrylfluorenylamine group, N-biphenylfluorenylamine group, etc., but are not limited thereto.

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

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

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

In this specification, the alkyl groups in the alkylamine group, N-arylalkylamine group, and N-alkylheteroarylamine group are the same as the examples of the alkyl groups 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 containing 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 simultaneously. For example, the heteroaryl group in the heteroarylamine group may be selected from examples of heteroaryl groups described below.

In this specification, examples of heteroaryl groups among N-arylheteroarylamine groups and N-alkylheteroarylamine groups are the same as examples of heteroaryl groups described later.

In the present specification, the silyl group may be an alkylsilyl group or an arylsilyl group, and may further be a trialkylsilyl group or a trialylsilyl group. The carbon number of the silyl group is not particularly limited, but is preferably 1 to 30, the alkylsilyl group may have 1 to 30 carbon atoms, and the arylsilyl group may have 5 to 30 carbon atoms. Specifically, it includes 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 , where R ₁₀₀ and R ₁₀₁ are the same or different, and are each independently hydrogen; heavy hydrogen; halogen; 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 substituted or unsubstituted heteroaryl groups 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, for example, 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 is preferably 6 to 60 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.

If the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable to have 10 to 60 carbon atoms. Specifically, polycyclic aryl groups include naphthyl group, anthryl group, phenanthryl group, triphenylenyl group, pyrenyl group, phenalenyl group, perylenyl group, chrysenyl group, fluorenyl group, and fluoranthenyl group. However, it is not limited to this.

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

When the fluorenyl group is substituted, , , and It can be etc. However, it is not limited to this.

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

In the present specification, the heterocyclic group includes one or more atoms other than carbon and a heterogeneous element. Specifically, the heterocyclic group may include one or more atoms selected from the group consisting of O, N, S, and P. . The number of carbon atoms is not particularly limited, but is preferably 1 to 60 carbon atoms, and 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 condensed ring thereof. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, Triazolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolyl group, quinazolyl group, quinoxalyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinolyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, phenanth These include, but are not limited to, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl.

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 heterocyclic group described above may be cited, except that the heteroaryl group and heteroarylene group are aromatic.

In this specification, “energy level” means the amount of energy. Therefore, even when the energy level is displayed in the minus (-) direction from the vacuum level, the energy level is interpreted to mean the absolute value of the corresponding energy value. For example, the highest occupied molecular orbital (HOMO) energy level refers to the distance from the vacuum level to the highest occupied molecular orbital. Additionally, 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 or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl group; or substituted or unsubstituted aryl group,

c is an integer from 0 to 4,

When c is 2 or more, 2 or more R3s are the same or different from each other,

* is the position bonded to Formula 1 above.

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

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

The definitions of L1, L2, R1 to R3, Az1, Az2, Ar2, X and a to c are the same as in Formulas 1 and 2.

In an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 2-1 to 2-12.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

[Formula 2-8]

[Formula 2-9]

[Formula 2-10]

[Formula 2-11]

[Formula 2-12]

In Formulas 2-1 to 2-12,

The definitions of L1, L2, R1 to R3, Az1, Az2, Ar2, X and a to c are the same as in Formulas 1 and 2.

In an exemplary embodiment of the present specification, one of Az1 and Az2 is -L10-Ar1, and the other is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.

According to another embodiment, one of Az1 and Az2 is -L10-Ar1, and the other is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, Az1 is -L10-Ar1.

According to another embodiment, Az1 is -L10-Ar1, and Az2 is hydrogen or deuterium.

In another embodiment, Az2 is -L10-Ar1, and Az1 is hydrogen or deuterium.

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 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 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; Substituted or unsubstituted biphenyl group; 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; Biphenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; Or it is a phenanthryl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, L10 is a direct bond; Or it is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

According to another embodiment, L10 is a direct bond; Or, it is an arylene group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium.

According to another embodiment, L10 is a direct bond; Or it is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to another embodiment, L10 is a direct bond; Or, it is an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

According to another embodiment, L10 is a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.

According to another embodiment, L10 is a direct bond; A phenylene group substituted or unsubstituted with deuterium; Or it is a naphthylene group substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; Or it is 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 or different from each other and are each independently directly bonded; Or, it is an arylene group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; Or it is 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 or different from each other and are each independently directly bonded; Or, it is an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

According to another embodiment, L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.

In another embodiment, L1 and L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; Or it is a naphthylene group substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

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

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

According to an exemplary embodiment of the present specification, b is an integer from 0 to 6, and when b is 2 or more, 2 or more R2s are the same or different from each other.

In an 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 embodiment, X is CR'R".

According to an exemplary embodiment of the present specification, R, R', R", and R3 in Formula 2 are the same or different from each other, and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or substituted Or it is an unsubstituted aryl group having 6 to 60 carbon atoms.

According to another embodiment, R, R', R", and R3 are the same as or different from each other, and each independently represents hydrogen; deuterium; an alkyl group of 1 to 30 carbon atoms substituted or unsubstituted with deuterium; or deuterium. It is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

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 are each independently 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 am.

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

In another exemplary embodiment, R' and R" are methyl groups.

According to another exemplary embodiment, R' and R" are phenyl groups.

In one 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 R3 are the same or different from each other.

In one embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or, it is a substituted or unsubstituted heteroelement and is a heterocycle having 2 to 60 carbon atoms containing at least 1 O.

According to another embodiment, Ar2 is an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium; Or, it is a heterocycle substituted or unsubstituted with deuterium and has 2 to 60 carbon atoms and contains at least 1 O.

According to another exemplary embodiment, Ar2 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthryl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted pyrenyl group; Substituted or unsubstituted fluorenyl group; Substituted or unsubstituted dibenzofuranyl group; Substituted or unsubstituted dibenzothiophenyl group; Substituted or unsubstituted carbazolyl group; or substituted or unsubstituted formula 1-A.

[Formula 1-A]

In Formula 1-A,

Y is O, S, NRa, or CRbRc,

Ra, Rb and Rc are the same or different from each other and are each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

means the position bound to L2.

According to another embodiment, Ar2 is a phenyl group unsubstituted or substituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; A phenanthryl group substituted or unsubstituted with deuterium; Triphenylenyl group substituted or unsubstituted with deuterium; Pyrenyl group substituted or unsubstituted with deuterium; A fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl group, and aryl group; Dibenzofuranyl group substituted or unsubstituted with deuterium; Dibenzothiophenyl group substituted or unsubstituted with deuterium; A carbazolyl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and aryl groups; Or it is the formula 1-A below, substituted or unsubstituted with deuterium.

[Formula 1-A]

In Formula 1-A,

Y is O, S, NRa, or CRbRc,

Ra, Rb and Rc are the same or different from each other and are each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

means the position bound to L2.

In an exemplary embodiment of the present specification, in the definition of a substituent in Formula 1-A, “substituted or unsubstituted” refers to deuterium; an alkyl group having 1 to 20 carbon atoms; Aryl group having 6 to 30 carbon atoms; and substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ra, Rb, and Rc are the same as or different from each other, and are each independently 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 it is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another embodiment, Ra, Rb, and Rc are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is 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, Rb and Rc are the same as or different from each other, and each independently represents a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.

According to an exemplary embodiment of the present specification, the dibenzofuran in which anthracene, Ar1, Ar2, and Formula 2 in Formula 1 are condensed each contain one or more deuterium.

According to an exemplary embodiment of the present specification, the dibenzofuran in which anthracene, Ar2, and Formula 2 in Formula 1 are condensed each contain one or more deuterium.

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

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

According to an exemplary embodiment of the present specification, the dibenzofuran in which formula 2 is condensed in formula 1 includes one or more deuterium.

According to an exemplary embodiment of the present specification, in Formula 1, anthracene and Ar1 each include one or more deuterium.

According to an exemplary embodiment of the present specification, the dibenzofuran in which anthracene, Ar1, and Formula 2 in Formula 1 are condensed each contain one or more deuterium.

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

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

In this specification, the deuterium substitution rate refers to the rate of deuterium substitution within the molecule, and can be confirmed through a known method. As an example, the distribution of deuterium substitution within a molecule can be determined using the following method. The following TLC-MS is a method for controlling the substitution ratio of deuterium during the synthesis of a compound.

1. Utilize TLC-MS (Thin-Layer Chromatography/Mass Spectrometry) (method to confirm synthesis process)

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 one embodiment of the present specification, Formula 1 is selected from the following compounds.

An exemplary embodiment of the present specification includes a first electrode; a second electrode provided opposite the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by the above-described formula (1). .

The organic light emitting device of the present specification can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention includes an organic material layer that includes a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection, an electron suppressing layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer that performs both electron transport and electron injection. It may have a structure including etc. However, the structure of the organic light emitting device is not limited to this and may include fewer or more organic material layers.

In one 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 hole transport layer includes the compound.

In one 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 electron injection layer includes the compound.

In one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound.

In one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host of the light-emitting layer.

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

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

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

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

Figure 1 illustrates the 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 this structure, the compound may be included in the light-emitting layer 3.

Figure 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 this 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).

In Figure 3, the anode (2), hole injection layer (5), hole transport layer (6), light emitting layer (7), electron transport layer (8), electron injection layer (9), and cathode (4) are sequentially placed on the substrate (1). The structure of a stacked organic light emitting device is illustrated. In this 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 deposit a metal, a conductive metal oxide, or an alloy thereof on a substrate. It can be manufactured by forming an anode by vapor deposition, 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, and then depositing a material that can be used as a cathode on it. You can. In addition to this method, an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material 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 performs electron injection and electron transport, an electron suppressing layer, a light emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously performs electron injection and electron transport. However, it is not limited to this and may have a single-layer structure. In addition, the organic material layer uses a variety of polymer materials to form a smaller number of layers by using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be manufactured in layers.

The anode is an electrode that injects holes, and the anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.

The cathode is an electrode that injects electrons, and the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO ₂ /Al.

The hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage. HOMO (highest occupied) of the hole injection material It is preferable that the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. organic substances, anthraquinone, polyaniline, and polythiophene series conductive polymers, etc., but are not limited to these.

The hole transport layer may play a role in facilitating the transport of holes. The hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.

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

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 that can emit light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; polyfluorene; Rubrene, etc., but is not limited to these.

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

The additional host materials include condensed aromatic ring derivatives or heterocycle-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.

The light-emitting dopants include PIQIr(acac)(bis(1-phenylsoquinoline)acetylacetonate iridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum). A phosphorescent material such as or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. If the light-emitting 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) can be used as the light-emitting dopant. However, it is not limited to this. If the light-emitting layer emits blue light, the light-emitting dopant may be a phosphorescent material such as (4,6-F ₂ ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), or distrylarylene (DSA). ), fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited to these.

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 play a role in facilitating the transport of electrons. The electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq ₃ ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these.

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

Examples of the metal complex compounds 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-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.

The organic light emitting device according to the present invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.

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

< Synthesis example >

Synthesis example 1. Synthesis of Compound 1

Synthesis example 1-1. Compound 1- of a synthesis

1-Bromo-2-fluorodibenzo[b,d]furan (80g, 302mmol) and (5-chloro-2-hydroxyphenyl)boronic acid (52.0g, 302mml) were dissolved in tetrahydrofuran (THF, 1500ml). After dissolving in , Pd(PPh ₃ ) ₄ (6.97g, 6.0 mmol) and 300ml 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 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), then K ₂ CO ₃ (83.5g, 604mmol) was added, and the mixture was refluxed and stirred for 2 hours. After cooling the reaction solution, it was poured into 3L of distilled water to produce a solid. The solid was filtered, dissolved in chloroform, extracted with water several times, 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 Compound 1

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

Synthesis example 2. Synthesis of Compound 2

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

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

Synthesis example 2-2. Synthesis of compound 2-b

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

Synthesis example 2-3. Synthesis of compound 2-c

Compound 2-b (1 eq) was dissolved in DMF (2000 ml), and then N-bromosuccinimide (1 eq) dissolved in 500 ml of DMF was slowly added dropwise. After stirring at room temperature for 2 hours, 3000ml of water was added dropwise. When a solid was formed, it was filtered, dissolved in chloroform, and extracted several times with distilled water. The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. Compound 2-c was obtained by purification through column chromatography. (yield 75%)

Synthesis example 2-4. Synthesis of Compound 2

Compound 2 was obtained in the same manner as Compound 2-c in Synthesis Example 1-3.

Synthesis example 3. Synthesis of Compound 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 4-bromo-1-chloro-3-fluorodibenzo[b,d]furan and 2-hydroxyphenylboronic acid.

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

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

Synthesis example 3-3. Synthesis of Compound 3

Compound 3 was obtained in the same manner as Compound 3-b in Synthesis Example 1-3.

Synthesis example 4. Synthesis of Compound 4

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

Compound 4-a was obtained in the same manner as in Synthesis Example 1-1 using 4-bromo-3-fluorodibenzo[b,d]furan.

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

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

Synthesis example 4-3. Synthesis of Compound 4

Compound 4 was obtained in the same manner as Compound 4-b in Synthesis Example 1-3.

Synthesis example 5. Synthesis of Compound 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 4-bromo-3-fluorodibenzo[b,d]furan and (6-chloro-2-hydroxyphenyl)boronic acid.

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

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

Synthesis example 5-3. Synthesis of compound 5

Compound 5 was obtained in the same manner as Compound 5-b in Synthesis Example 1-3.

Synthesis example 6. Synthesis of Compound 6

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

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

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

Compound 5-b was obtained in the same manner as Compound 6-a in Synthesis Example 1-2.

Synthesis example 6-3. Synthesis of compound 6

Compound 6 was obtained in the same manner as Compound 6-b in Synthesis Example 1-3.

Synthesis example 7. Synthesis of Compound 7

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

Compound 7-a was synthesized in the same manner as in Synthesis Example 1-1 using Compound 5 and 1-bromo-4-chlorobenzene.

Synthesis example 7-2. Synthesis of compound 7

Compound 7 was synthesized in the same manner as Compound 7-a in Synthesis Example 1-3.

Synthesis example 8. Synthesis of Compound 8

Synthesis example 8-1. Synthesis of compound 8-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, it was filtered, dissolved in chloroform, and extracted several times with distilled water. The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. Compound 8-a was obtained by purification through column chromatography.

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

Compound 8-b was obtained in the same manner as in Synthesis Example 1-1 using compound 8-a and (5-chloro-2-fluorophenyl)boronic acid.

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

Compound 8-c was obtained in the same manner as Compound 8-b in Synthesis Example 1-2.

Synthesis example 8-4. Synthesis of compound 8

Compound 8 was obtained in the same manner as Compound 8-c in Synthesis Example 1-3.

Synthesis example 9. Synthesis of Compound 9

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

Compound 9-a was obtained in the same manner as in Synthesis Example 1-1 using 4-bromo-3-fluorodimethylfluorene and (5-chloro-2-hydroxyphenyl)boronic acid.

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

Compound 9-b was obtained in the same manner as Compound 9-a in Synthesis Example 1-2.

Synthesis example 9-3. Synthesis of compound 9

Compound 9 was obtained in the same manner as Compound 9-b in Synthesis Example 1-3.

Synthesis example 10. Synthesis of Compound 10

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

Compound 10-a was obtained in the same manner as in Synthesis Example 1-1 using 1-bromo-2-iodo-3-fluorobenzene.

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

Compound 10-b was obtained in the same manner as Compound 10-a in Synthesis Example 1-2.

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

Compound 10-c was obtained in the same manner as in Synthesis Example 1-1 using compound 10-b and 2-nitroboronic acid.

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

Compound 10-c (1 eq) and PPh ₃ (3 eq) were dissolved in 600 ml 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 then distilled under reduced pressure to remove chloroform. Compound 10-d (yield 60%) was obtained by purification using column chromatography.

Synthesis example 10-5. Synthesis of compound 10-e

Compound 10-d (1 eq) and iodobenzene (1 eq) were dissolved in 250ml of DMF, and then CS ₂ CO ₃ (2 eq) and CuI (0.1 eq) were added. The temperature was raised to 120°C and stirred for 16 hours. After cooling the reaction solution, 1L of ethyl acetate was added, and then it was transferred to a separatory funnel and extracted once with an aqueous ammonia solution and a total of three times with 1L of distilled water. The organic layer was collected, treated with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. Compound 10-e was obtained by purification using column chromatography. (yield 57%)

Synthesis example 10-6. Synthesis of compound 10

Compound 10 was obtained in the same manner as Compound 10-e in Synthesis Example 1-3.

Synthesis example 11. Synthesis of Compound 11

Synthesis example 11-1. Synthesis of compound 11-a

Compound 11-a was obtained in the same manner as in Synthesis Example 1-1 using 1-bromo-2-fluorodimethylfluorene.

Synthesis example 11-2. Synthesis of compound 11-b

Compound 11-b was obtained in the same manner as Compound 11-a in Synthesis Example 1-2.

Synthesis example 11-3. Synthesis of compound 11

Compound 11 was obtained in the same manner as Compound 11-b in Synthesis Example 1-3.

Synthesis example 12. Synthesis of BH-A

Synthesis example 12-1. Synthesis of compound 12-a

After dissolving 2-bromoanthracene (100 g, 389mmol) and 1-naphthaleneboronic acid (66.9g, 389mmol) in THF (2000ml), Pd(PPh ₃ ) ₄ (9.0g, 7.8mmol) and 2M K ₂ CO ₃ 400ml 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 12-a (94 g, yield 80%).

Synthesis example 12-2. Synthesis of compound 12-b

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

Synthesis example 12-3. Synthesis of compound 12-c

After dissolving Compound 10-b (73 g, 189 mmol) and Compound 1 (72.6 g, 189 mmol) in THF (1000 ml), Pd(PPh ₃ ) ₄ (4.4 g, 3.8 mmol) and 200 ml of 2M K ₂ CO ₃ aqueous solution were added. 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 12-c (52 g, yield 72%).

Synthesis example 12-4. Synthesis of compound 12-d

Compound 12-c (52g, 136mmol) was dissolved in 600ml of DMF, and then N-bromosuccinimide (24.2g, 136mmol) dissolved in 100ml 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 filtered, dissolved in chloroform, and extracted several times with distilled water. Compound 12-d was obtained by recrystallization from ethyl acetate. (41g, yield 66%)

Synthesis example 12-5. Synthesis of BH-A

Compound 12-d (41 g, 64 mmol) and phenylboronic acid (7.8 g, 64 mmol) were dissolved in THF (500ml), then Pd(PPh ₃ ) ₄ (1.5g, 1.3mmol) 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 confirmed by mass. [cal. m/s: 636.7, exp. m/s (M+H) 637.7]

Synthesis example 13. Synthesis of BH-B

BH-B was obtained in the same manner as in Synthesis Example 12, using 1-naphthaleneboronic acid instead of phenylboronic acid. The final compound was confirmed by mass. [cal. m/s: 686.8, exp. m/s (M+H) 687.8]

Synthesis example 14. Synthesis of BH-C

BH-C was obtained in the same manner as in Synthesis Example 12, using 2-naphthaleneboronic acid instead of phenylboronic acid. The final compound was confirmed by mass. [cal. m/s: 686.8, exp. m/s (M+H) 687.8]

Synthesis example 15. Synthesis of BH-D

BH-D was obtained in the same manner as in Synthesis Example 12, using 9-phenanthrylboronic acid instead of phenylboronic acid. The final compound was confirmed by mass. [cal. m/s: 736.9, exp. m/s (M+H) 737.9]

Synthesis example 16. Synthesis of BH-E

BH-E was obtained in the same manner as in Synthesis Example 12, using Compound 2 instead of Compound 1. The final compound was confirmed by mass. [cal. m/s: 636.8, exp. m/s (M+H) 637.8]

Synthesis example 17. Synthesis of BH-F

BH-F was obtained in the same manner as in Synthesis Example 12, using 1-naphthaleneboronic acid instead of phenylboronic acid and Compound 2 instead of Compound 1. The final compound was confirmed by mass. [cal. m/s: 686.8, exp. m/s (M+H) 687.8]

Synthesis example 18. Synthesis of BH-G

BH-G was obtained in the same manner as in Synthesis Example 12, using 2-naphthaleneboronic acid instead of phenylboronic acid and Compound 3 instead of Compound 1. The final compound was confirmed by mass. [cal. m/s: 686.8, exp. m/s (M+H) 687.8]

Synthesis example 19. Synthesis of BH-H

BH-H was obtained in the same manner as in Synthesis Example 12, using 9-phenanthrylboronic acid instead of 1-naphthaleneboronic acid and Compound 3 instead of Compound 1. The final compound was confirmed by mass. [cal. m/s: 686.8, exp. m/s (M+H) 687.8]

Synthesis example 20. Synthesis of BH-I

BH-I was obtained in the same manner as in Synthesis Example 12, using phenylboronic acid instead of 1-naphthaleneboronic acid and compound 4 instead of compound 1. The final compound was confirmed by mass. [cal. m/s: 586.7, exp. m/s (M+H) 587.7]

Synthesis example 21. Synthesis of BH-J

BH-J was obtained in the same manner as in Synthesis Example 12, using phenylboronic acid instead of 1-naphthaleneboronic acid and compound 5 instead of compound 1. The final compound was confirmed by mass. [cal. m/s: 586.7, exp. m/s (M+H) 587.7]

Synthesis example 22. Synthesis of BH-K

BH-K was obtained in the same manner as in Synthesis Example 12, using phenylboronic acid instead of 1-naphthaleneboronic acid and Compound 6 instead of Compound 1. The final compound was confirmed by mass. [cal. m/s: 586.7, exp. m/s (M+H) 587.7]

Synthesis example 23. Synthesis of BH-L

BH-L was obtained in the same manner as in Synthesis Example 12, using compound 7 instead of compound 1. The final compound was confirmed by mass. [cal. m/s: 712.8, exp. m/s (M+H) 713.8]

Synthesis example 24. Synthesis of BH-M

BH-M was obtained in the same manner as in Synthesis Example 12, using compound 8 instead of compound 1. The final compound was confirmed by mass. [cal. m/s: 652.8, exp. m/s (M+H) 653.8]

Synthesis example 25. Synthesis of BH-N

BH-N was obtained in the same manner as in Synthesis Example 12, using Compound 9 instead of Compound 1. The final compound was confirmed by mass. [cal. m/s: 662.8, exp. m/s (M+H) 663.8]

Synthesis example 26. Synthesis of BH-O

BH-O was obtained in the same manner as in Synthesis Example 12, using Compound 10 instead of Compound 1. The final compound was confirmed by mass. [cal. m/s: 711.9, exp. m/s (M+H) 712.9]

Synthesis example 27. Synthesis of BH-P

BH-P was obtained in the same manner as in Synthesis Example 12, using Compound 11 instead of Compound 1. The final compound was confirmed by mass. [cal. m/s: 662.8, exp. m/s (M+H) 663.8]

Synthesis example 28. Synthesis of 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 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 with MgSO ₄ and recrystallized with ethyl acetate to obtain BH-Q. (15g, yield 75%) The final compound was confirmed by mass. In the deuterium substitution reaction, molecular weight appears as a distribution. [cal. m/s: 664.9, exp. m/s (M+H) 658 ~ 665 ]

Synthesis example 29. Synthesis of compound 12

Compound 12 was obtained in the same manner as in Synthesis Example 28 using 2-chloroanthracene. The final compound was confirmed by mass. In the deuterium substitution reaction, molecular weight appears as a distribution. [cal. m/s: 221.7, exp. m/s (M+H) 220 ~ 222]

Synthesis example 29. Synthesis of BH-R

BH-R was obtained in the same manner as in Synthesis Example 12, using Compound 12 instead of 2-bromoanthracene. The final compound was confirmed by mass. In the deuterium substitution reaction, molecular weight appears as a distribution. [cal. m/s: 643.8, exp. m/s (M+H) 642 ~ 644 ]

Synthesis example 30. Synthesis of BH-S

BH-S was obtained in the same manner as in Synthesis Example 12, using compound 12 instead of 2-bromoanthracene and compound 9 instead of compound 1. The final compound was confirmed by mass. In the deuterium substitution reaction, molecular weight appears as a distribution. [cal. m/s: 669.9, exp. m/s (M+H) 668 ~ 670]

Synthesis example 31. Synthesis of BH-T

BH-T was obtained in the same manner as in Synthesis Example 12, using compound 12 instead of 2-bromoanthracene and compound 10 instead of compound 1. The final compound was confirmed by mass. In the deuterium substitution reaction, molecular weight appears as a distribution. [cal. m/s: 718.9, exp. m/s (M+H) 717 ~ 719 ]

< Experiment example . Manufacturing of organic light emitting devices>

Example One.

A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 150 nm was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent from Fischer Co. was used, and distilled water filtered secondarily using a filter from Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using nitrogen plasma and then transported to a vacuum evaporator. On the ITO transparent electrode prepared in this way, the following HAT-CN compound was thermally vacuum deposited to a thickness of 5 nm to form a hole injection layer. Next, 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. Subsequently, BH-A as a host and BD-A (weight ratio 97:3) as a dopant were simultaneously vacuum deposited to form a 20 nm thick light emitting layer. Next, ETL was vacuum deposited to a thickness of 20 nm to form an electron transport layer. Subsequently, LiF was vacuum deposited to a thickness of 0.5 nm to form an electron injection layer. Next, aluminum was deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic light emitting device.

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

Example 2 to 20 and Comparative example 1 to 3.

An organic light-emitting device was manufactured in the same manner as Example 1, except that the compounds listed in Table 1 below were used as the host of the light-emitting layer instead of compound BH-A.

In the organic light emitting devices manufactured 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 the initial luminance was measured at a current density of 20 mA/cm ² The time to reach 95% of the comparison (LT) was measured, and the results are shown in Table 1 below.

compound 10mA / cm ² Measures L.T. ( T95% ) ( luminescent layer host) Driving voltage ( Vop ) Luminous efficiency (Cd/A) Example One BH-A 3.56 7.21 157 Example 2 BH-B 3.62 7.38 162 Example 3 BH-C 3.60 7.30 164 Example 4 BH-D 3.60 7.40 147 Example 5 BH-E 3.55 6.84 137 Example 6 BH-F 3.57 6.92 131 Example 7 BH-G 3.57 6.88 131 Example 8 BH-H 3.60 7.01 125 Example 9 BH-I 3.56 7.15 155 Example 10 BH-J 3.53 7.02 150 Example 11 BH-K 3.58 7.02 153 Example 12 BH-L 3.55 7.15 152 Example 13 BH-M 3.54 6.74 120 Example 14 BH-N 3.49 6.59 123 Example 15 BH-O 3.50 6.63 126 Example 16 BH-P 3.49 6.55 124 Example 17 BH-Q 3.56 7.21 236 Example 18 BH-R 3.56 7.22 204 Example 19 BH-S 3.49 6.60 160 Example 20 BH-T 3.50 6.65 164 Comparative example One BH-1 3.68 6.34 94 Comparative example 2 BH-2 3.68 6.33 103 Comparative example 3 BH-3 3.33 4.12 20

Examples 1 to 20 using the compound represented by Formula 1 of the present invention all showed characteristics of low voltage and high efficiency compared to Comparative Examples 1 to 3, and also showed excellent lifespan. Additionally, it can be seen from Examples 17 to 20 that the lifespan of devices using deuterium-substituted compounds is significantly improved.

Comparative Example 1 used compound BH-1, which is Ar1 hydrogen of Formula 2, and it can be seen that the driving voltage is higher and the efficiency and lifespan are lower than those of Examples 1 to 20. In addition, the compound BH-2 used in Comparative Example 2 contains deuterium in Formula 1, but Ar1 is hydrogen, and has an increased lifespan compared to Comparative Example 1, but has a shorter lifespan compared to the Examples.

Compound BH-3 used in Comparative Example 3 has a structure in which a heterocyclic ring not containing O is bonded to the 5-ring condensed heterocyclic ring containing O in Formula 1, and has the highest electronegativity among N, S and O. Since it does not contain large O, injection of electrons is not as easy as in the embodiment of the present application, 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. In this case, the conjugate length of the molecule becomes too long to have an energy gap similar to that of the dopant, resulting in a lower driving voltage, but Energy transfer becomes difficult. Therefore, it can be confirmed that substitution only for Ar1 leads to improvements 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)

Compound represented by Formula 1:
[Formula 1]

In Formula 1,
R1 and R2 are the same or different from each other and are each independently hydrogen; heavy hydrogen; 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,
Either Az1 or Az2 is -L10-Ar1, and the other is hydrogen; heavy hydrogen; 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,
L1, L2 and L10 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms,
Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms,
Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or, it is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms containing one or more of O, S, and N,
a is an integer from 0 to 5, b is an integer from 0 to 6,
When a is 2 or more, 2 or more R1s are the same or different from each other,
When b is 2 or more, 2 or more R2s are the same or different from each other,
* combines with Formula 2 below,
[Formula 2]

In Formula 2,
X is O, S, NR, or CR'R",
R, R', R" and R3 are the same or different from each other, and each independently represents 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,
c is an integer from 0 to 4,
When c is 2 or more, 2 or more R3s are the same or different from each other,
* is the position bonded to Formula 1 above. The compound according to claim 1, wherein Formula 1 is represented by the following Formula 1-1 or 1-2:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,
The definitions of L1, L2, R1 to R3, Az1, Az2, Ar2, X and a to c are the same as in Formulas 1 and 2. The method according to claim 1, wherein Ar1 is a substituted or unsubstituted phenyl group; Or a compound that is a substituted or unsubstituted naphthyl group. The method according to claim 1, wherein L1 and L2 are the same or different from each other, and are each independently directly bonded; Substituted or unsubstituted phenylene group; Or a compound that is 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 heterocyclic group having 2 to 60 carbon atoms containing one or more O as a substituted or unsubstituted heteroelement. The compound according to claim 1, wherein the compound contains one or more deuterium. The compound according to claim 1, wherein the deuterium substitution rate of the compound is 10% to 100%. The compound according to claim 1, wherein Formula 1 is selected from the following compounds:

. first electrode; a second electrode provided opposite the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 8. . The organic light-emitting device 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 a light-emitting layer, and the light-emitting layer includes the compound. The organic light-emitting device of claim 9, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host of the light-emitting layer. The organic light emitting device of claim 13, wherein the light emitting layer further includes a dopant.