阅读说明：本技术 多环化合物及包含其的有机发光器件 (Polycyclic compound and organic light emitting device including the same ) 是由 禁水井 洪玩杓 金京嬉 徐尚德 于 2019-11-19 设计创作，主要内容包括：本说明书提供由化学式1表示的化合物及包含其的有机发光器件。(The present specification provides a compound represented by chemical formula 1 and an organic light emitting device including the same.)

1. A compound represented by the following chemical formula 1:

chemical formula 1

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

either X1 or X2 is O or S, the other is O, S or CRR',

r1, R2, R and R' are the same as or different from each other and each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,

2 or more of R3 to R6 are represented by the following chemical formula 2, and the others are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

cy1 and Cy2, which are the same or different from each other, are each independently a substituted or unsubstituted ring,

chemical formula 2

In the chemical formula 2,

l1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar1 and Ar2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or are combined with each other to form a substituted or unsubstituted heterocyclic ring,

represents a position bonded to 1 or more of R3 to R6.

2. The compound of claim 1, wherein the Cy1 and Cy2 are the same or different from each other, each independently a substituted or unsubstituted monocyclic to tricyclic ring.

3. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 1-1 to 1-4:

chemical formula 1-1

Chemical formula 1-2

Chemical formulas 1 to 3

Chemical formulas 1 to 4

In the chemical formulas 1-1 to 1-4,

r1 to R6, Cy2, X1 and X2 are the same as defined in the chemical formula 1,

x3 to X6, which are identical to or different from each other, are each independently O, S or CR "R'",

r21 to R36, R "and R'" which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring.

4. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2-1:

chemical formula 2-1

In the chemical formula 2-1,

r1, R2, Cy1, Cy2, X1 and X2 are the same as defined in said chemical formula 1,

r101 and R102 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group,

l11 to L14, which are identical to or different from one another, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar11 to Ar14, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or adjacent groups of Ar11 to Ar14 are bonded to each other to form a substituted or unsubstituted heterocyclic ring.

5. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formulae 1-5 or 1-6:

chemical formulas 1 to 5

Chemical formulas 1 to 6

In the chemical formulas 1 to 5 and 1 to 6,

r1, R2, Cy1, Cy2, X1 and X2 are the same as defined in said chemical formula 1,

r103 to R108 and Ar101 to Ar104, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group,

n1 and n2 are each an integer of 0 to 8, and when n1 and n2 are each 2 or more, the substituents in parentheses of 2 or more are the same as or different from each other.

6. The compound according to claim 4, wherein the chemical formula 2-1 is represented by any one of the following chemical formulae 2-1-1 to 2-1-4:

chemical formula 2-1

Chemical formula 2-1-2

Chemical formula 2-1-3

Chemical formula 2-1-4

In the chemical formulas 2-1-1 to 2-1-4,

r1, R2, Cy2, X1, X2, L11 to L14, Ar11 to Ar14, R101 and R102 are the same as defined in said chemical formula 2-1,

x7 to X10, which are identical to or different from each other, are each independently O, S or CRaRb,

r41 to R56, Ra and Rb are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring.

7. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following compounds:

8. an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic material layers provided between the first electrode and the second electrode,

1 or more of the organic layers comprise a compound of any one of claims 1 to 7.

9. The organic light emitting device of claim 8, wherein the organic layer comprises a hole injection layer or a hole transport layer comprising the compound.

10. An organic light-emitting device according to claim 8 wherein the organic layer comprises an electron-transporting layer or an electron-injecting layer comprising the compound.

11. The organic light emitting device of claim 8, wherein the organic layer comprises a light emitting layer comprising the compound.

12. The organic light emitting device according to claim 8, wherein the organic layer comprises a light emitting layer containing the compound as a dopant of the light emitting layer.

13. The organic light emitting device according to claim 11, wherein the light emitting layer further comprises a compound represented by the following chemical formula H:

chemical formula H

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

l21 to L23, which are identical to or different from one another, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

r201 to R207 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

ar21 to Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

a is 0 or 1.

Technical Field

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

The present application claims priority of korean patent application No. 10-2018-0142545, which was filed to korean patent office at 19.11.2018, the entire contents of which are incorporated herein.

Background

In this specification, an organic light-emitting device refers to a light-emitting device using an organic semiconductor material, and requires exchange of holes and/or electrons between an electrode and the organic semiconductor material. Organic light emitting devices can be broadly classified into the following two types according to the operation principle. The first type is a light emitting device in which an exciton (exiton) is formed in an organic layer by a photon flowing from an external light source into the device, the exciton is separated into an electron and a hole, and the electron and the hole are transferred to different electrodes to be used as a current source (voltage source). The second type is a light-emitting device in which holes and/or electrons are injected into an organic semiconductor material layer forming an interface with an electrode by applying a voltage or current to 2 or more electrodes, and the light-emitting device operates by the injected electrons and holes.

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron inhibiting layer, an electron transport layer, an electron injection layer, or the like. In the structure of such an organic light emitting device, if a voltage is applied between the electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and excitons (exiton) are formed when the injected holes and electrons meet each other, and light is emitted when the excitons transition to the ground state again. Such an organic light emitting device is known to have characteristics of self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and the like.

Materials used as the organic layer in the organic light emitting device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron inhibiting substances, electron transport materials, electron injection materials, and the like, according to functions. The light-emitting materials include blue, green, and red light-emitting materials, and yellow and orange light-emitting materials required for realizing a more natural color, depending on the light-emitting color.

In addition, as a light emitting material, a host/dopant system may be used for the purpose of increasing color purity and increasing light emitting efficiency by energy transfer. The principle is that when a small amount of a dopant having a smaller energy band gap and excellent light emission efficiency than a host mainly constituting a light emitting layer is mixed in the light emitting layer, excitons generated in the host are transferred to the dopant to emit light with high efficiency. In this case, since the wavelength of the host is shifted to the wavelength range of the dopant, light having a desired wavelength can be obtained according to the kind of the dopant used

In order to fully utilize the excellent characteristics of the organic light emitting device, the materials constituting the organic layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron suppressing material, an electron transporting material, and an electron injecting material, are stable and effective, and therefore, development of new materials is continuously required.

Disclosure of Invention

Technical subject

The present specification describes compounds and organic light emitting devices comprising the same.

Means for solving the problems

One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[ chemical formula 1]

In the above-described chemical formula 1,

either X1 or X2 is O or S, the other is O, S or CRR',

r1, R2, R and R' are the same as or different from each other and each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,

2 or more of R3 to R6 are represented by the following chemical formula 2, and the others are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

cy1 and Cy2, which are the same or different from each other, are each independently a substituted or unsubstituted ring,

[ chemical formula 2]

In the above-described chemical formula 2,

l1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar1 and Ar2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or are combined with each other to form a substituted or unsubstituted heterocyclic ring,

represents a position bonded to 1 or more of R3 to R6.

In addition, the present invention provides an organic light emitting device, comprising: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound.

Effects of the invention

The compound described in this specification can be used as a material for an organic layer of an organic light-emitting device.

In the case of manufacturing an organic light-emitting device including the compound according to an embodiment of the present specification, an organic light-emitting device excellent in light-emitting efficiency, having a low driving voltage, high efficiency, and a long lifetime can be obtained.

Drawings

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

[ description of symbols ]

1: substrate

2: anode

3: luminescent layer

4: cathode electrode

5: hole injection layer

6: hole transport layer

6 a: a first hole transport layer

6 b: second hole transport layer

7: luminescent layer

8: layer for simultaneous electron injection and electron transport

Detailed Description

The present specification will be described in more detail below.

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

[ chemical formula 1]

In the above-described chemical formula 1,

either X1 or X2 is O or S, the other is O, S or CRR',

r1, R2, R and R' are the same as or different from each other and each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,

2 or more of R3 to R6 are represented by the following chemical formula 2, and the others are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

cy1 and Cy2, which are the same or different from each other, are each independently a substituted or unsubstituted ring,

[ chemical formula 2]

In the above-described chemical formula 2,

l1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar1 and Ar2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or are combined with each other to form a substituted or unsubstituted heterocyclic ring,

represents a position bonded to 1 or more of R3 to R6.

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

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

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

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

In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium (-D), a halogen group, a cyano (-CN), a nitro group, a hydroxyl group, a silyl group, a boryl group, an alkyl group, an alkoxy group, a cycloalkyl group, an aryl group, an amino group, and a heterocyclic group, or a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. For example, "a substituent in which 2 or more substituents are linked" may be a terphenyl group. That is, the terphenyl group may be an aryl group, or may be interpreted as a substituent in which 3 phenyl groups are linked.

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

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

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

In this specification, the boron group may be represented BY-BY_dY_eThe above-mentioned chemical formula is Y_dAnd Y_eMay each be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl. The boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

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 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, and n-octyl.

In the present specification, the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkoxy group has 1 to 30 carbon atoms. According to another embodiment, the alkoxy group has 1 to 20 carbon atoms. According to another embodiment, the alkoxy group has 1 to 10 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, methoxy, ethoxy, propoxy, and butoxy.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there are, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylene group, a triphenyl group, a perylene group,Examples of the group include, but are not limited to, a fluorenyl group, a triphenylene group, and the like.

In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure.

When the fluorenyl group is substituted, the compound may beIsospirofluorene group;(9, 9-dimethylfluorenyl group) andand substituted fluorenyl groups such as (9, 9-diphenylfluorenyl) and the like. But is not limited thereto.

In the present specification, the heterocyclic group is a cyclic group containing 1 or more of N, O, S and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuryl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuryl, benzonaphthothienyl, indenocarbazolyl and the like.

In the present specification, the amine group may be represented by-NY_fY_gThe above-mentioned chemical formula is Y_fAnd Y_gMay each be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. The amino group may be specifically, but not limited to, a dimethylamino group, a diphenylamino group, a dicyclohexylamino group, or the like.

In the present specification, the above description of the heterocyclic group can be applied to the heteroaryl group except for the heteroaryl group.

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

In the present specification, a substituted or unsubstituted ring formed by bonding adjacent groups to each other, and a "ring" refers to a hydrocarbon ring or a heterocyclic ring.

The hydrocarbon ring may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic, and may be selected from the cycloalkyl group and the aryl group described above, with the difference that the hydrocarbon ring is a 2-valent group.

In the present specification, the aromatic hydrocarbon ring may be substituted with the aromatic hydrocarbon ring described above except that it has a valence of 2.

The heterocyclic ring may be used as described above for the heterocyclic group except that it has a valence of 2.

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

In this specification, the above description on heteroaryl groups can be applied except that heteroarylene groups are 2-valent groups.

According to an embodiment of the present disclosure, any one of X1 and X2 is O or S, and the other is O, S or CRR'.

According to another embodiment, any one of the above X1 and X2 is O or S, and the other one is O or S.

According to another embodiment, the above X1 and X2 are O or S.

According to another embodiment, each of X1 and X2 is O.

According to another embodiment, each of X1 and X2 is S.

According to another embodiment, any one of the above X1 and X2 is O, and the other one is S.

According to another embodiment, any one of X1 and X2 described above is O and the remaining one is CRR'.

According to another embodiment, any one of the above X1 and X2 is S and the other is CRR'.

In one embodiment of the present specification, R and R' are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

According to another embodiment, the above R and R', which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, R and R' are the same as or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, the above R and R', equal to or different from each other, are each independently hydrogen, deuterium, or an alkyl group having 1 to 20 carbon atoms.

In another embodiment, the above R and R', equal to or different from each other, are each independently hydrogen, deuterium, substituted or unsubstituted methyl, or substituted or unsubstituted ethyl.

According to another embodiment, the above R and R', equal to or different from each other, are each independently hydrogen, deuterium, methyl or ethyl.

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

According to an embodiment of the present disclosure, the Cy1 and the Cy2 may be the same or different and each independently represent a substituted or unsubstituted ring having 6 to 60 carbon atoms.

In another embodiment, the Cy1 and Cy2 are the same as or different from each other, and each is independently a substituted or unsubstituted ring having 6 to 30 carbon atoms.

According to another embodiment, the above Cy1 and Cy2, which are the same or different from each other, are each independently a substituted or unsubstituted one-to three-ring.

According to another embodiment, the above Cy1 and Cy2, which are the same or different from each other, are each independently a substituted or unsubstituted one-to three-ring having 6 to 60 carbon atoms.

In another embodiment, the Cy2 is substituted or unsubstituted benzene.

According to another embodiment, the Cy2 is benzene.

In another embodiment, Cy1 is a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted aromatic heterocycle containing O or S as a heteroatom.

According to another embodiment, the Cy1 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, or an aromatic heterocyclic ring having 2 to 30 carbon atoms and containing O or S as a heteroatom.

In another embodiment, the Cy1 is substituted or unsubstituted benzene, substituted or unsubstituted indene, substituted or unsubstituted benzofuran, or substituted or unsubstituted benzothiophene.

In another embodiment, the Cy1 is benzene, indene, benzofuran, or benzothiophene.

According to an embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4.

[ chemical formula 1-1]

[ chemical formulas 1-2]

[ chemical formulas 1-3]

[ chemical formulas 1 to 4]

In the above chemical formulas 1-1 to 1-4,

r1 to R6, Cy2, X1 and X2 are the same as defined in the above chemical formula 1,

x3 to X6, which are identical to or different from each other, are each independently O, S or CR "R'",

r21 to R36, R "and R'" which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring.

According to an embodiment of the present disclosure, the X3 to X6 are the same or different and each is independently O or S.

According to an embodiment of the present specification, the above R "and R'" are the same or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

According to another embodiment, the above R "and R'" are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, the above R "and R'" are the same as or different from each other and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, the above R "and R'" are the same or different from each other and are each independently hydrogen, deuterium, or an alkyl group having 1 to 20 carbon atoms.

In another embodiment, the above R "and R'" are the same or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted methyl, or substituted or unsubstituted ethyl.

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

According to an embodiment of the present disclosure, R21 to R36 are the same or different and each independently hydrogen or deuterium.

According to an embodiment of the present disclosure, R1 and R2 are the same or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or combine with each other to form a substituted or unsubstituted ring.

In another embodiment, R1 and R2 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to another embodiment, R1 and R2 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

According to another embodiment, R1 and R2 which are the same as or different from each other, are each independently hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium or an alkyl group having 1 to 20 carbon atoms, or are combined with each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

According to another embodiment, R1 and R2, which are the same or different from each other, are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, or are combined with each other to form fluorene substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

In another embodiment, R1 and R2 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group, or are combined with each other to form a substituted or unsubstituted fluorene.

In another embodiment, R1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, methyl, or phenyl substituted or unsubstituted with methyl, or are combined with each other to form fluorene substituted or unsubstituted with tert-butyl.

According to another embodiment, the above R1 and R2, equal to or different from each other, are each independently hydrogen, deuterium, methyl, phenyl or tolyl, or combine with each other to form fluorene substituted or unsubstituted with tert-butyl.

According to one embodiment of the present specification, 1 or more of the R3 to R6 are represented by the following chemical formula 2, and the others are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[ chemical formula 2]

In the above-described chemical formula 2,

l1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar1 and Ar2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or are combined with each other to form a substituted or unsubstituted heterocyclic ring,

represents a position bonded to 1 or more of R3 to R6.

According to another embodiment, 2 or more of the above R3 to R6 are represented by the above chemical formula 2, and the others are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to another embodiment, 2 of the above R3 to R6 are represented by the above chemical formula 2, and the remaining 2 are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to another embodiment, 2 of the above R3 to R6 are represented by the above chemical formula 2, and the remaining 2 are each independently hydrogen or deuterium.

In one embodiment of the present specification, the R4 and the R6 are represented by the chemical formula 2, and the R3 and the R5 are each independently hydrogen or deuterium.

According to an embodiment of the present specification, 2 substituents represented by chemical formula 2 are the same as each other.

According to an embodiment of the present disclosure, L1 and L2 are the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

According to another embodiment, each of L1 and L2 which are the same or different from each other, is independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

In another embodiment, L1 and L2, which are the same or different from each other, are each independently a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 2 to 30 carbon atoms.

In another embodiment, L1 and L2 are the same as or different from each other, and each is independently a direct bond, a phenylene group, a biphenylene group, a naphthylene group, a 2-valent fluorenyl group, a 2-valent carbazolyl group, a 2-valent dibenzofuranyl group, or a 2-valent dibenzothiophenyl group.

In another embodiment, L1 and L2 are the same as or different from each other, and each is independently a direct bond or an arylene group having 6 to 20 carbon atoms.

In another embodiment, L1 and L2 are the same or different from each other and are each independently a direct bond or a phenylene group.

In another embodiment, each of L1 and L2 is a direct bond.

According to one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with each other to form a substituted or unsubstituted heterocyclic ring.

According to another embodiment, Ar1 and Ar2 which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or are combined with each other to form a substituted or unsubstituted heterocyclic ring.

In another embodiment, Ar1 and Ar2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms and containing O, S or N as a heteroatom, or are combined with each other to form a substituted or unsubstituted heterocyclic ring containing O, S or N as a heteroatom.

According to another embodiment, Ar1 and Ar2 are the same as or different from each other, and each is independently hydrogen; deuterium; an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a cyano group, a halogen group, a substituted or unsubstituted silyl group, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a heterocyclic group of carbon number 2 to 30 which contains O, S or N as a heteroatom and is substituted or unsubstituted with 1 or more substituents selected from deuterium, a cyano group, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of carbon number 1 to 20, and a substituted or unsubstituted aryl group of carbon number 6 to 30, or combine with each other to form a heterocyclic ring containing O, S or N as a heteroatom and which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a cyano group, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of carbon number 1 to 20, and a substituted or unsubstituted aryl group of carbon number 6 to 30.

According to another embodiment, Ar1 and Ar2 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a cyano group, a halogen group, a trialkylsilyl group having 3 to 60 carbon atoms, and an alkyl group having 1 to 20 carbon atoms; or a heterocyclic group of 2 to 30 carbon atoms containing O, S or N as a heteroatom which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a cyano group, a halogen group, a trialkylsilyl group having 3 to 60 carbon atoms, an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms, or a heterocyclic ring containing O, S or N as a heteroatom which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a cyano group, a halogen group, a trialkylsilyl group having 3 to 60 carbon atoms, an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms.

In another embodiment, Ar1 and Ar2 which are the same as or different from each other, are each independently an aryl group having 6 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, and Ar1 and Ar2 may contain 1 or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a trialkylsilyl group having 3 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an alkyl group having 1 to 10 carbon atoms substituted with a halogen group, an aryl group having 6 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms substituted with deuterium.

In another embodiment, each of Ar1 and Ar2 is a phenyl group, and is bonded to each other to form a carbazole, and the carbazole may include 1 or more substituents selected from deuterium, a cyano group, a halogen group, a trialkylsilyl group having 3 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an alkyl group having 1 to 10 carbon atoms substituted with a halogen group, an aryl group having 6 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms substituted with deuterium.

In another embodiment, Ar1 and Ar2, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group, or are combined with each other to form a substituted or unsubstituted carbazole.

In another embodiment, Ar1 and Ar2 which are the same as or different from each other, are each independently a phenyl group, a biphenyl group, a naphthyl group, a 9, 9-dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, or a carbazolyl group, and Ar1 and Ar2 may contain 1 or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a trialkylsilyl group having 1 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an alkyl group having 1 to 10 carbon atoms substituted with a halogen group, an aryl group having 6 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms substituted with deuterium.

In another embodiment, each of Ar1 and Ar2 is a phenyl group, and is bonded to each other to form a carbazole, and the carbazole may include 1 or more substituents selected from deuterium, a cyano group, a halogen group, a trialkylsilyl group having 3 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an alkyl group having 1 to 10 carbon atoms substituted with a halogen group, an aryl group having 6 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms substituted with deuterium.

According to another embodiment, Ar1 and Ar2 are the same as or different from each other, and each is independently hydrogen; deuterium; a phenyl group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a trimethylsilyl group, an alkyl group having 1 to 10 carbon atoms which is substituted with deuterium, and an alkyl group having 1 to 10 carbon atoms which is substituted with a halogen group; biphenyl substituted or unsubstituted with 1 or more substituents selected from deuterium, cyano, a halogen group, a trimethylsilyl group, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, and an alkyl group having 1 to 10 carbon atoms substituted with a halogen group; naphthyl substituted or unsubstituted with 1 or more substituents selected from deuterium, cyano, a halogen group, a trimethylsilyl group, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, and an alkyl group having 1 to 10 carbon atoms substituted with a halogen group; a fluorenyl group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a trimethylsilyl group, an alkyl group having 1 to 10 carbon atoms which is substituted with deuterium, and an alkyl group having 1 to 10 carbon atoms which is substituted with a halogen group; a dibenzofuranyl group which is unsubstituted or substituted with 1 or more substituents selected from deuterium, an alkyl group having 1 to 10 carbon atoms which is substituted with deuterium, an aryl group having 6 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms which is substituted with deuterium; dibenzothienyl substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an aryl group having 6 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms substituted with deuterium; or a carbazolyl group substituted with 1 or more substituents selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an aryl group having 6 to 30 carbon atoms substituted with deuterium, and an aryl group having 6 to 30 carbon atoms substituted with deuterium, or a carbazole group substituted with 1 or more substituents selected from deuterium, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an aryl group having 6 to 30 carbon atoms substituted with deuterium, and an aryl group having 6 to 30 carbon atoms substituted with deuterium.

According to an embodiment of the present disclosure, the chemical formula 1 is represented by the following chemical formula 2-1.

[ chemical formula 2-1]

In the above chemical formula 2-1,

r1, R2, Cy1, Cy2, X1 and X2 are the same as defined in the above chemical formula 1,

r101 and R102 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group,

l11 to L14, which are identical to or different from one another, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar11 to Ar14, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or adjacent groups of Ar11 to Ar14 are bonded to each other to form a substituted or unsubstituted heterocyclic ring.

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

[ chemical formula 2-2]

In the above chemical formula 2-2,

cy1, Cy2, X1, X2, R1, R2, R101, R102, L11 to L14, Ar11 to Ar14 are defined as in the above chemical formula 2-1.

According to an embodiment of the present disclosure, the above-mentioned-N (-L11-Ar11) (-L12-Ar12) and-N (-L14-Ar13) (-L14-Ar14) are the same as each other.

According to an embodiment of the present specification, the above chemical formula 2-1 is represented by any one of the following chemical formulae 2-1-1 to 2-1-4.

[ chemical formula 2-1-1]

[ chemical formula 2-1-2]

[ chemical formulas 2-1-3]

[ chemical formulas 2-1-4]

In the above chemical formulas 2-1-1 to 2-1-4,

r1, R2, Cy2, X1, X2, L11 to L14, Ar11 to Ar14, R101 and R102 are the same as defined in the above chemical formula 2-1,

x7 to X10, which are identical to or different from each other, are each independently O, S or CRaRb,

r41 to R56, Ra and Rb are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring.

According to an embodiment of the present disclosure, the X7 to X10 are the same or different and each is independently O or S.

According to an embodiment of the present disclosure, Ra and Rb are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

According to another embodiment, Ra and Rb as described above, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, Ra and Rb as described above, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, Ra and Rb as described above, which are the same or different from each other, are each independently hydrogen, deuterium, or an alkyl group having 1 to 20 carbon atoms.

In another embodiment, Ra and Rb as described above, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted methyl group, or a substituted or unsubstituted ethyl group.

According to another embodiment, Ra and Rb above, equal to or different from each other, are each independently hydrogen, deuterium, methyl or ethyl.

According to an embodiment of the present disclosure, R41 to R56 are the same or different and each independently hydrogen or deuterium.

According to an embodiment of the present specification, R101 and R102 are the same or different from each other and each independently hydrogen or deuterium.

According to an embodiment of the present disclosure, L11 to L14 are the same or different and each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

According to another embodiment, the above L11 to L14, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

In another embodiment, L11 to L14 which are the same or different from each other, are each independently a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 2 to 30 carbon atoms.

In another embodiment, L11 to L14 are the same as or different from each other, and each is independently a direct bond, a phenylene group, a biphenylene group, a naphthylene group, a 2-valent fluorenyl group, a 2-valent carbazolyl group, a 2-valent dibenzofuranyl group, or a 2-valent dibenzothiophenyl group.

In another embodiment, L11 to L14 are the same or different and each independently a direct bond or an arylene group having 6 to 20 carbon atoms.

In another embodiment, the above L11 to L14, which are the same or different from each other, are each independently a direct bond or a phenylene group.

In another embodiment, each of L11 to L14 is a direct bond.

According to one embodiment of the present disclosure, Ar11 to Ar14 are the same or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups of Ar11 to Ar14 are bonded to each other to form a substituted or unsubstituted heterocyclic ring.

According to another embodiment, Ar11 to Ar14 which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or adjacent groups among Ar11 to Ar14 are bonded to each other to form a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms.

In another embodiment, Ar11 to Ar14 which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms and containing O, S or N as a heteroatom, or adjacent groups of Ar11 to Ar14 are bonded to each other to form a substituted or unsubstituted heterocyclic ring having 4 to 30 carbon atoms.

According to another embodiment, Ar11 to Ar14 are the same or different from each other, and each is independently hydrogen; deuterium; an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a cyano group, a halogen group, a substituted or unsubstituted silyl group, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a heterocyclic group of carbon number 2 to 30 which contains O, S or N as a heteroatom and is substituted or unsubstituted with 1 or more substituents selected from deuterium, a cyano group, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of carbon number 1 to 20, and a substituted or unsubstituted aryl group of carbon number 6 to 30, or combine with each other to form a heterocyclic ring containing O, S or N as a heteroatom and which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a cyano group, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of carbon number 1 to 20, and a substituted or unsubstituted aryl group of carbon number 6 to 30.

In another embodiment, Ar11 to Ar14 are the same or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a cyano group, a halogen group, a trialkylsilyl group having 3 to 60 carbon atoms, and an alkyl group having 1 to 20 carbon atoms; or a heterocyclic group of 2 to 30 carbon atoms containing O, S or N as a heteroatom which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a cyano group, a halogen group, a trialkylsilyl group having 3 to 60 carbon atoms, an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms, or a heterocyclic ring containing O, S or N as a heteroatom which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a cyano group, a halogen group, a trialkylsilyl group having 3 to 60 carbon atoms, an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms.

In another embodiment, Ar11 to Ar14 which are the same as or different from each other, are each independently an aryl group having 6 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, and Ar1 and Ar2 may contain 1 or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a trialkylsilyl group having 3 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an alkyl group having 1 to 10 carbon atoms substituted with a halogen group, an aryl group having 6 to 30 carbon atoms and an aryl group substituted with deuterium.

In another embodiment, Ar11 and Ar12 are each phenyl groups, and are bonded to each other to form a carbazole, and the carbazole may include 1 or more substituents selected from deuterium, a cyano group, a halogen group, a trialkylsilyl group having 3 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an alkyl group having 1 to 10 carbon atoms substituted with a halogen group, an aryl group having 6 to 30 carbon atoms, and an aryl group substituted with deuterium.

In another embodiment, Ar13 and Ar14 are each phenyl groups, and are bonded to each other to form a carbazole, and the carbazole may include 1 or more substituents selected from deuterium, a cyano group, a halogen group, a trialkylsilyl group having 3 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an alkyl group having 1 to 10 carbon atoms substituted with a halogen group, an aryl group having 6 to 30 carbon atoms, and an aryl group substituted with deuterium.

In another embodiment, Ar11 to Ar14 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted dibenzofuranyl group, or adjacent groups of Ar11 to Ar14 are bonded to each other to form a substituted or unsubstituted carbazole.

According to another embodiment, Ar11 to Ar14 are the same or different from each other, and each is independently hydrogen; deuterium; a phenyl group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a trimethylsilyl group, an alkyl group having 1 to 10 carbon atoms which is substituted with deuterium, and an alkyl group having 1 to 10 carbon atoms which is substituted with a halogen group; biphenyl substituted or unsubstituted with 1 or more substituents selected from deuterium, cyano, a halogen group, a trimethylsilyl group, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, and an alkyl group having 1 to 10 carbon atoms substituted with a halogen group; naphthyl substituted or unsubstituted with 1 or more substituents selected from deuterium, cyano, a halogen group, a trimethylsilyl group, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, and an alkyl group having 1 to 10 carbon atoms substituted with a halogen group; a fluorenyl group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a trimethylsilyl group, an alkyl group having 1 to 10 carbon atoms which is substituted with deuterium, and an alkyl group having 1 to 10 carbon atoms which is substituted with a halogen group; a dibenzofuranyl group which is unsubstituted or substituted with 1 or more substituents selected from deuterium, an alkyl group having 1 to 10 carbon atoms which is substituted with deuterium, an aryl group having 6 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms which is substituted with deuterium; dibenzothienyl substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an aryl group having 6 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms substituted with deuterium; or a carbazolyl group substituted with 1 or more substituents selected from deuterium, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an aryl group having 6 to 30 carbon atoms substituted with deuterium, and an aryl group having 6 to 30 carbon atoms substituted with deuterium, or adjacent 2 of Ar11 to Ar14 are combined with each other to form a carbazole substituted with 1 or more substituents selected from deuterium, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an aryl group having 6 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms substituted with deuterium.

According to an embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 1-5 or 1-6.

[ chemical formulas 1 to 5]

[ chemical formulas 1 to 6]

In the above chemical formulas 1 to 5 and 1 to 6,

r1, R2, Cy1, Cy2, X1 and X2 are the same as defined in the above chemical formula 1,

r103 to R108 and Ar101 to Ar104, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group,

n1 and n2 are each an integer of 0 to 8, and when n1 and n2 are each 2 or more, the substituents in parentheses of 2 or more are the same as or different from each other.

According to an embodiment of the present disclosure, R103 to R108 are the same or different and each independently hydrogen or deuterium.

According to an embodiment of the present specification, R107 and R108 are the same or different from each other and each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present specification, R107 and R108 are the same or different from each other and each independently hydrogen or deuterium.

In one embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to another embodiment, Ar101 to Ar104 described above, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In another embodiment, Ar101 to Ar104 above, which are the same or different from each other, are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms which contains O, S or N as a heteroatom.

According to another embodiment, Ar101 to Ar104 above, equal to or different from each other, are each independently hydrogen; deuterium; an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a cyano group, a halogen group, a substituted or unsubstituted silyl group, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a heterocyclic group of O, S or N as a hetero atom, which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a cyano group, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group of 6 to 30 carbon atoms.

In another embodiment, the Ar101 to Ar104 may be the same as or different from each other, and each independently an aryl group having 6 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, and the Ar101 to Ar104 may include 1 or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a trialkylsilyl group having 3 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an alkyl group having 1 to 10 carbon atoms substituted with a halogen group, an aryl group having 6 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms substituted with deuterium.

In another embodiment, Ar101 to Ar104 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

In another embodiment, the Ar101 to Ar104 may be the same as or different from each other and each independently represent a phenyl group, a biphenyl group, a naphthyl group, a 9, 9-dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group, and the Ar101 to a104 may contain 1 or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a trialkylsilyl group having 1 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an alkyl group having 1 to 10 carbon atoms substituted with a halogen group, an aryl group having 6 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms substituted with deuterium.

According to another embodiment, Ar101 to Ar104 above, equal to or different from each other, are each independently hydrogen; deuterium; a phenyl group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a trimethylsilyl group, an alkyl group having 1 to 10 carbon atoms which is substituted with deuterium, and an alkyl group having 1 to 10 carbon atoms which is substituted with a halogen group; biphenyl substituted or unsubstituted with 1 or more substituents selected from deuterium, cyano, a halogen group, a trimethylsilyl group, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, and an alkyl group having 1 to 10 carbon atoms substituted with a halogen group; naphthyl substituted or unsubstituted with 1 or more substituents selected from deuterium, cyano, a halogen group, a trimethylsilyl group, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, and an alkyl group having 1 to 10 carbon atoms substituted with a halogen group; a fluorenyl group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a trimethylsilyl group, an alkyl group having 1 to 10 carbon atoms which is substituted with deuterium, and an alkyl group having 1 to 10 carbon atoms which is substituted with a halogen group; a dibenzofuranyl group which is unsubstituted or substituted with 1 or more substituents selected from deuterium, an alkyl group having 1 to 10 carbon atoms which is substituted with deuterium, an aryl group having 6 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms which is substituted with deuterium; dibenzothienyl substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an aryl group having 6 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms substituted with deuterium; or a carbazolyl group substituted with 1 or more substituents selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms substituted with deuterium, an aryl group having 6 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms substituted with deuterium.

According to an embodiment of the present disclosure, the chemical formula 1 may be represented by any one of the following compounds.

According to an embodiment of the present specification, the compound of chemical formula 1 may be produced as shown in the following reaction formula 1. The following reaction formula 1 describes a synthesis process of a partial compound corresponding to chemical formula 1 of the present application, but various compounds corresponding to chemical formula 1 of the present application can be synthesized by the synthesis process shown in the following reaction formula 1, substituents can be combined by a method known in the art, and the kind, position and number of substituents can be changed according to a technique known in the art.

< reaction formula 1>

Intermediate 3(IM-3) was synthesized by Suzuki coupling (Suzuki coupling) reaction of intermediate 1(IM-1) and intermediate 2(IM-2), and intermediate 4(IM-4) containing a tertiary alcohol was obtained from the ester of intermediate 3(IM-3) using the Grignard reagent (Grignard reagent). Intermediate 4(IM-4) is subjected to ring-closing reaction (ring-closing reaction) with concentrated sulfuric acid to give intermediate 5(IM-5), and intermediate 5(IM-5) is subjected to Buckwald amination (Buckwald amination) to give the final compound.

Further, the intermediate 3(IM-3) can be subjected to intramolecular fusion reaction using concentrated sulfuric acid to produce a ketone (ketone), and then subjected to bromination reaction to produce the intermediate 6 (IM-6). Subsequently, nucleophilic reaction of ketone with aryl lithium followed by reaction with sulfuric acid yielded intermediate 7 (IM-7). The final compounds can be obtained by a Buhward amination reaction using various arylamines.

In the above reaction formulae, Cy1, X1, X2, and Ar1 to Ar4 are defined as in the above chemical formula 1, and R is defined as R1 and R2 in the above chemical formula 1, respectively.

In this specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the above chemical formula 1. In addition, in the present specification, by introducing various substituents into the core structure of the above-described structure, the HOMO and LUMO levels of the compound can also be adjusted.

Further, by introducing various substituents into the core structure having the above-described structure, a compound having the inherent characteristics of the introduced substituents can be synthesized. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, an electron suppression material, a light-emitting layer material, and an electron transport layer material, which are used in the production of an organic light-emitting device, into the core structure, a material satisfying the conditions required for each organic layer can be synthesized.

In addition, an organic light emitting device according to the present specification is characterized by comprising: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include the compound represented by chemical formula 1.

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

The organic layer can be formed by using the above compound not only by a vacuum evaporation method but also by a solution coating method in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

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

In the organic light emitting device of the present specification, the above organic layer may include an electron transport layer or an electron injection layer, and the above electron transport layer or the electron injection layer may contain the above-mentioned compound.

In the organic light emitting device of the present specification, the above organic layer may include a hole injection layer or a hole transport layer, and the above hole injection layer or hole transport layer may contain the above-mentioned compound.

In the organic light-emitting device of the present specification, the above-mentioned organic layer includes a light-emitting layer containing the above-mentioned compound.

According to another embodiment, the organic layer includes a light emitting layer, and the light emitting layer may include the above-mentioned compound as a dopant of the light emitting layer.

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer may include the compound as a dopant of the light-emitting layer and may further include a host.

An organic light emitting device according to an embodiment of the present specification includes a light emitting layer including a compound represented by the following chemical formula H in addition to the compound represented by the chemical formula 1. Specifically, the compound described above is included as a dopant of the light-emitting layer, and the compound represented by the following chemical formula H is included as a host of the light-emitting layer.

[ chemical formula H ]

In the above-mentioned chemical formula H,

l21 to L23, which are identical to or different from one another, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

r21 to R27, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

ar21 to Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

a is 0 or 1.

In one embodiment of the present specification, when a is 0, hydrogen or deuterium is bonded to the position-L23-Ar 23.

In one embodiment of the present specification, L21 to L23, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, L21 to L23, which are the same or different from each other, are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms comprising N, O or S.

In one embodiment of the present specification, L21 to L23, which are the same or different from each other, are each independently a direct bond; an arylene group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms; or a heteroarylene group of carbon number 2 to 30 which is substituted or unsubstituted with deuterium, an alkyl group of carbon number 1 to 10, an aryl group of carbon number 6 to 30, or a heteroaryl group of carbon number 2 to 30.

In one embodiment of the present specification, L21 to L23, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted 2-valent dibenzofuranyl group, or a substituted or unsubstituted 2-valent dibenzothiophenyl group.

In one embodiment of the present specification, L21 to L23, which are the same or different from each other, are each independently a direct bond, phenylene, biphenylene, or naphthylene, and L21 to L23 may each contain 1 or more deuterium.

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

In one embodiment of the present specification, L22 is a direct bond or phenylene.

In one embodiment of the present description, L23 is a direct bond.

In one embodiment of the present description, L1 may contain deuterium. Specifically, L1 contains 1 or more deuterium.

In one embodiment of the present description, L2 may contain deuterium. Specifically, L2 contains 1 or more deuterium.

In one embodiment of the present description, L3 may contain deuterium. Specifically, L3 contains 1 or more deuterium.

In one embodiment of the present specification, Ar21 to Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar21 to Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ar21 to Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenalene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted naphthobenzofuryl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted naphthobenzothienyl group.

In one embodiment of the present disclosure, Ar21 to Ar23, which are the same or different from each other, are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a dibenzothienyl group, or a naphthobenzofuranyl group, and Ar21 to Ar23 may each include 1 or more deuterium groups.

In one embodiment of the present specification, Ar21 and Ar22, which are the same or different from each other, are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzofuranyl, naphthobenzofuranyl, dibenzothiophenyl, or naphthobenzothiophenyl.

In one embodiment of the present specification, Ar21 and Ar22, which are the same or different from each other, are each independently phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, or dibenzofuranyl.

In one embodiment of the present specification, Ar23 is phenyl, biphenyl, or naphthyl.

In one embodiment of the present specification, Ar23 is naphthyl.

In one embodiment of the present description, Ar1 may contain deuterium. Specifically, Ar1 contains 1 or more deuterium.

In one embodiment of the present description, Ar2 may contain deuterium. Specifically, Ar2 contains 1 or more deuterium.

In one embodiment of the present description, Ar3 may contain deuterium. Specifically, Ar3 contains 1 or more deuterium.

In one embodiment of the present specification, Ar21 and Ar22 are different from each other.

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

In one embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl and Ar22 is a substituted or unsubstituted heteroaryl.

In one embodiment of the present specification, Ar21 is an aryl group substituted or unsubstituted with deuterium, and Ar22 is an aryl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar21 is aryl substituted or unsubstituted with deuterium, and Ar22 is heteroaryl substituted or unsubstituted with deuterium.

In one embodiment of the present specification, R21 to R27, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R201 to R207, which are the same or different from each other, are each independently hydrogen or deuterium.

In one embodiment of the present specification, R201 to R207 are hydrogen.

In one embodiment of the present specification, R201 to R207 are deuterium.

In one embodiment of the present specification, the chemical formula H is represented by the following chemical formula H01 or H02.

[ chemical formula H01]

[ chemical formula H02]

In the above chemical formulae H01 and H02,

l21 to L23 and Ar21 to Ar23 are as defined in formula H, D is deuterium, k1 is an integer from 0 to 8, and k2 is an integer from 0 to 7.

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

When the compound of the present invention is contained as a dopant of the light emitting layer and the above chemical formula H is contained as a host, the content of the dopant may be contained in an amount of 1 to 20 parts by weight, preferably 1 to 5 parts by weight, based on 100 parts by weight of the host. When the above range is satisfied, the organic light emitting device manufactured has advantages of low driving voltage and high light emitting efficiency.

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a dopant of the light-emitting layer, and further includes a fluorescent host or a phosphorescent host, and may include another organic compound, a metal, or a metal compound as a dopant.

The compound represented by the above chemical formula H may include 1 species or 2 or more species in the organic layer (specifically, the light-emitting layer). Specifically, the first host represented by the above chemical formula H and the second host represented by the above chemical formula H may be included in the organic layer.

The weight ratio of the first body represented by the above chemical formula H to the second body represented by the above chemical formula H is 95:5 to 5:95, and more preferably 30:70 to 70: 30.

In another embodiment, the first body and the second body are different from each other.

In another embodiment, Ar21 and Ar22 of the first body represented by formula H above, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group; ar21 of the second body represented by the above formula H is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted heteroaryl group.

As another example, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a dopant of the light-emitting layer, and further includes a fluorescent host or a phosphorescent host, and may be used together with an iridium (Ir) dopant.

According to another embodiment, the organic layer includes a light emitting layer, and the light emitting layer may include the compound as a host of the light emitting layer.

As another example, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host of the light-emitting layer and may further include a dopant.

In the organic light emitting device of the present invention, the organic layer may include an electron-inhibiting layer, and the electron-inhibiting layer may contain the compound.

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

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

For example, the organic light emitting device may have a stacked structure as shown below, but is not limited thereto.

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

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

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

(4) Anode/hole transport layer/luminescent layer/electron transport layer/electron injection layer/cathode

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

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

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

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

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

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

(11) Anode/hole transport layer/light-emitting layer/hole inhibiting layer/electron transport layer/cathode

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

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

(14) Anode/hole injection layer/hole transport layer/light-emitting layer/hole inhibiting layer/electron transport layer/electron injection layer/cathode

(15) Anode/hole injection layer/hole transport layer/light-emitting layer/layer for simultaneous electron injection and electron transport/cathode

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

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

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

Fig. 3 illustrates a structure of an organic light emitting device in which an anode 2, a hole injection layer 5, a first hole transport layer 6a, a second hole transport layer 6b, a light emitting layer 7, a layer 8 for simultaneously performing electron injection and electron transport, and a cathode 4 are sequentially stacked on a substrate 1. In the structure as described above, the above-described compound may be contained in the above-described hole injection layer 5, the first hole transport layer 6a, the second hole transport layer 6b, the light-emitting layer 7, or the layer 8 that performs both electron injection and electron transport.

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

The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer that performs both hole injection and hole transport, an electron suppression layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that performs both electron injection and electron transport, and the like. The organic layer can be produced as a smaller number of layers by a solvent process (solvent process) other than the vapor deposition method, for example, spin coating, dip coating, blade coating, screen printing, inkjet printing, thermal transfer printing, or the like, using various polymer materials.

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

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

The hole injection layer is a layer that functions to smoothly inject holes from the anode into the light-emitting layer, and the hole injection substance is a substance that can inject holes from the anode well at a low voltage, and preferably, the HOMO (highest occupied molecular orbital) of the hole injection substance is interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrine), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers. The thickness of the hole injection layer may be 1 to 150 nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the hole injection property can be prevented from being lowered, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the driving voltage can be prevented from being increased to increase the movement of holes when the thickness of the hole injection layer is too large.

The hole transport layer may have a single layer structure or a multilayer structure having 2 or more layers, and serves to smoothly transport holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

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

The light-emitting layer may emit red, green or blue light, and may be formed of a phosphorescent substance or a fluorescent substance. The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) isAzole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.

As a host material of the light-emitting layer, there are aromatic fused ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the aromatic fused ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene derivative, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder furan compound, a pyrimidine derivative, and the like, but is not limited thereto.

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

The electron transport layer and the light-emitting layer may be provided with a hole-inhibiting layer that inhibits holes from reaching the cathode, and the hole-inhibiting layer may be formed under the same conditions as the hole-injecting layer. Specifically, there areAn oxadiazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex (aluminum complex), and the like, but the present invention is not limited thereto.

The electron transport layer may beSo as to play a role in making the transmission of electrons smooth. The electron transport material is a material capable of injecting electrons from the cathode and transferring the electrons to the light-emitting layer, and is preferably a material having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the electron transport property can be prevented from being lowered, and when the thickness of the electron transport layer is 50nm or less, there is an advantage that the driving voltage can be prevented from being increased to increase the movement of electrons when the thickness of the electron transport layer is too thick.

The electron injection layer can perform a function of smoothly injecting electrons. As the electron-injecting substance, the following compounds are preferred: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and having an excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

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

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

Modes for carrying out the invention

Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments described herein may be modified into various forms, and the scope of the present description should not be construed as being limited to the embodiments described in detail below. The embodiments of the present description are provided to more fully describe the present description to those skilled in the art.

Synthesis example

Synthesis example 1 Synthesis of intermediate A-4

Under nitrogen atmosphere, the mixture of intermediate A-1(50.0g, 0.167mol) and intermediate A-2(45.67g, 0.20mol), Bis (tri-tert-butylphosphine) palladium (0) [ Bis (tri-tert-butylphosphine) -palladium (0)](0.85g，1.67mmol)、K₂CO₃A flask of (69.2g, 0.50mol) and 550mL Tetrahydrofuran (THF) was heated with stirring for 4 hours. After the reaction solution was cooled to room temperature, water and ethyl acetate (ethyl acetate) were added to conduct extraction and washing. The organic layer was recovered and the extraction solvent was removed, followed by purification by recrystallization (chloroform/hexane), whereby 50.4g of intermediate A-3 was obtained.

Intermediate A-3(20.0g, 0.050mol) was dissolved in 200mL of THF under a nitrogen atmosphere, cooled to 10 deg.C, and then methyl magnesium bromide (88.7mL, 0.124mol, 1.4M in THF/toluene solution) was slowly added dropwise. After stirring at room temperature for 2 hours, it was cooled to 0 ℃. After ethyl acetate (ethyl acetate) was added, water was slowly added, and after completion of the reaction, the temperature was returned to normal temperature again, and extraction and washing were performed. After recovering the organic layer and removing the extraction solvent, purification was performed by column chromatography (ethyl acetate/hexane), thereby obtaining 17.2g of intermediate A-4. MS [ [ M + H ] + ] ═ 403

Synthesis example 2 Synthesis of intermediate A-6

After intermediate A-4(15.5g, 0.038mol) was dissolved in 30mL of acetic acid and 90mL of chloroform (chloroform) under a nitrogen atmosphere, a catalytic amount of concentrated sulfuric acid was added and the mixture was stirred at 50 ℃ for 4 hours. The reaction solution was cooled to room temperature and then filtered. The filter cake was dissolved in toluene and saturated NaHCO was used₃Aqueous solution (saturated aq₃) After neutralization, extraction and washing are carried out. The organic layer was recovered and the extraction solvent was removed, followed by purification by recrystallization (ethyl acetate/hexane), to obtain 12.0g of intermediate A-5.

To intermediate A-5(12.0g, 0.031mol) dissolved in 300mL of N, N-Dimethylformamide (N, N-Dimethylformamide) and being stirred, N-Bromosuccinimide (5.8g, 0.033mmol) dissolved in 15mL of N, N-Dimethylformamide (N, N-Dimethylformamide) was slowly dropped using a funnel (dropping funnel) for 30 minutes under a nitrogen atmosphere, and then stirred at room temperature for 1 hour. 300mL of a Saturated aqueous sodium thiosulfate solution (Satured aq. sodium thiosulfate) was added, stirred at room temperature for 30 minutes, and then filtered. The filter cake was dissolved in toluene and saturated NaHCO was added₃(saturated NaHCO₃) Extraction and washing are carried out. The organic layer was recovered and the extraction solvent was removed, followed by purification by recrystallization (ethyl acetate/hexane), whereby 11.1g of intermediate A-6 was obtained.

Synthesis example 3 Synthesis of Compound A-P-1

A flask containing intermediate A-6(2.5g, 15.39mmol) and diphenylamine (diphenylamine) (1.9g, 11.3mmol), Bis (tri-tert-butylphosphine) palladium (0) [ Bis (tri-tert-butylphosphine) -palladium (0) ] (0.06g), sodium tert-butoxide (1.81g) and 35mL of toluene was refluxed and stirred under a nitrogen atmosphere for 12 hours. After the reaction solution was cooled to room temperature, water and toluene were added, and extraction and washing were performed. After the organic layer was recovered and the extraction solvent was removed, column chromatography (chloroform/hexane) was performed to purify the extract, thereby obtaining 3.1g of compound a. MS: [ M + H ] + ═ 685

Synthesis examples 4 to 6 < Synthesis of Compound A-P-2 to Compound A-P-4>

Compounds A-P-2(2.4g), A-P-3(3.4g) and A-P-4(2.8g) were synthesized by the same method as that for the synthesis of the compound A-P-1 of Synthesis example 3, using the intermediate A-6 and the above-mentioned intermediates A-7, A-8 and A-9, respectively. As a result of mass spectrometry of each solid obtained, peaks were observed at [ M + H + ] ═ 865, 949, and 871, respectively.

Synthesis example 7 Synthesis of intermediate B-2

After intermediate A-3(30.0g, 0.074mol) was dissolved in 260mL of chloroform (chloroform) under a nitrogen atmosphere, methanesulfonic acid (methanesulfonic acid) (14.4mL, 0.22mol) was added and the mixture was stirred under reflux for 12 hours. The reaction solution was cooled to normal temperature and filtered, and the filter cake was dissolved in 260mL of N, N-Dimethylformamide (N, N-Dimethylformamide). Bromine (bromine) (3.8mL, 0.074mmol) was slowly added dropwise to the reaction solution under a nitrogen atmosphere, and stirred at room temperature for 3 hours. 400mL of a Saturated aqueous sodium thiosulfate solution (Satured aq. sodium thiosulfate) was added, stirred at room temperature for 30 minutes, and then filtered. The filter cake was dissolved in toluene and Tetrahydrofuran (THF), saturated NaHCO was added₃(saturated NaHCO₃) Extraction and washing are carried out. The organic layer was recovered and the extraction solvent was removed, followed by purification by recrystallization (toluene), whereby 14.8g of intermediate B-1 was obtained.

Under a nitrogen atmosphere, 2-phenylbromide dissolved in 400mL of Tetrahydrofuran (THF)(2-phenylbromobenzene) (7.26g, 31.2mmol) was cooled to-78 deg.C and n-butyllithium (n-butyllithium) (12.7mL, 31.8mmol, 2.5M in hexane) was slowly added dropwise. After stirring at the same temperature for 1 hour, intermediate B-1(14.0g, 31.2mmol) was added to the reaction solution. Slowly returned to normal temperature over 2 hours, and further stirred for 2 hours. After ethyl acetate (ethyl acetate) was added, water was slowly added to complete the reaction, and the reaction was returned to normal temperature again, followed by extraction and washing. After the organic layer was collected and the extraction solvent was removed, the product was dissolved in 400mL of toluene, and methanesulfonic acid (3.04mL, 46.8mmol) was added thereto and stirred at room temperature for 4 hours. Adding water and toluene, extracting the organic layer, and extracting with saturated NaHCO₃Aqueous solution (sat₃) And (6) washing. The organic layer was recovered and the extraction solvent was removed, followed by purification by recrystallization (ethyl acetate/hexane), whereby 12.1g of intermediate B-2 was obtained. MS: [ M + H]+＝585

Synthesis example 8 Synthesis of Compound B-P-1

A flask containing intermediate B-2(2.3g, 3.9mmol) and N- (3-fluorophenyl) -2-methylaniline [ N- (3-fluorophenyl) -2-methylaniline ] (1.74g, 8.6mmol), Bis (tri-tert-butylphosphine) palladium (0) [ Bis (tri-tert-butylphosphine) palladium (0) ] (40mg), sodium tert-butoxide (1.3g) and 25mL of xylene was refluxed and stirred under a nitrogen atmosphere for 8 hours. After the reaction solution was cooled to room temperature, water and toluene were added, and extraction and washing were performed. The organic layer was recovered and the extraction solvent was removed, followed by column chromatography (chloroform/hexane for purification, thereby obtaining 2.1g of compound B-P-1. MS: [ M + H ] + ═ 871

Synthesis examples 9 to 12 < Synthesis of Compound B-P-2 to Compound B-P-5>

Compounds B-P-2(2.0g), B-P-3(2.9g), B-P-4(2.2g) and B-P-5(1.8g) were prepared by the same method as that for the synthesis of Compound B-P-1 of Synthesis example 8, using intermediate B-2 and intermediates A-10 to A-13 described above, respectively. As a result of mass spectrometry of each solid obtained, peaks were observed at [ M + H + ]. 1015, 929, 807, and 1019, respectively.

Synthesis example 13 Synthesis of intermediate C-3

1-bromo-4-methylbenzene (1-bromo-4-methylbenezene) (22.8mL, 0.186mol) dissolved in 400mL of Tetrahydrofuran (THF) was cooled to-78 deg.C under a nitrogen atmosphere, and n-butyllithium (n-butylllithium) (76mL, 0.19mol, 2.5M in hexane) was slowly added dropwise. After stirring at the same temperature for 1 hour, intermediate A-3(30.0g, 0.074mol) was added to the reaction solution. Slowly returned to normal temperature over 2 hours, and further stirred for 1 hour. After ethyl acetate (ethyl acetate) was added, water was slowly added to complete the reaction, and then the reaction was returned to normal temperature again, followed by extraction and washing. After the organic layer was recovered and the extraction solvent was removed, the product was dissolved in 200mL of toluene, followed by addition of methanesulfonic acid (14.5mL, 0.224mol), and stirring under reflux for 4 hours. Adding water and toluene, extracting the organic layer, and extracting with saturated NaHCO₃Aqueous solution (sat₃) And (6) washing. The organic layer was recovered and the extraction solvent was removed, followed by purification by recrystallization (ethyl acetate/hexane), whereby 19.6g of intermediate C-2 was obtained.

To intermediate C-2(17.4g, 0.032mol) dissolved in 260mL of N, N-Dimethylformamide (N, N-Dimethylformamide) and being stirred, N-Bromosuccinimide (6.4g, 0.036mmol) dissolved in 60mL of N, N-Dimethylformamide (N, N-Dimethylformamide) was slowly dropped over a funnel (dropping funnel) for 30 minutes under a nitrogen atmosphere, and then stirred at room temperature for 1 hour. 400mL of a Saturated aqueous sodium thiosulfate solution (Satured aq. sodium thiosulfate) was added, stirred at room temperature for 30 minutes, and then filtered. The filter cake was dissolved in toluene and added toAnd NaHCO₃(saturated NaHCO₃) Extraction and washing are carried out. After recovering the organic layer and removing the extraction solvent, purification was performed by recrystallization (ethyl acetate/hexane), thereby obtaining 14.4g of intermediate C-3. MS: [ M + H]+＝615

Synthesis examples 14 to 17 < Synthesis of Compound C-P-1 to Compound C-P-4>

Each of the compounds C-P-1(3.4g), C-P-2(3.8g), C-P-3(2.8g) and C-P-4(2.9g) was prepared by a method similar to that for the synthesis of Compound B-P-1 of Synthesis example 8, using intermediate C-2(3.0g) and intermediates A-14 to A-17 described above, respectively. As a result of mass spectrometry of each solid obtained, peaks were observed at [ M + H + ] ═ 865, 1098, 1045, and 981.

Synthesis example 18 Synthesis of intermediate F-4

Intermediate F-2(27.6g) was produced by the same method as that for the synthesis of intermediate A-3 of Synthesis example 1, using intermediate A-1(25.0g) and intermediate F-1 described above.

Subsequently, by a method similar to that for the synthesis of intermediate B-2 of Synthesis example 7, intermediate F-4(9.3g) was produced from intermediate F-2(26.0 g). MS: [ M + H + ] ═ 617

Synthesis examples 19 to 21 < Synthesis of Compounds F-P-1 to F-P-3>

Compounds F-P-1(2.6g), F-P-2(2.4g) and F-P-3(2.1g) were prepared in the same manner as for the synthesis of Compound B-P-1 of Synthesis example 8, using intermediate F-4(3.0g) and intermediates A-18 to A-20 described above, respectively. As a result of mass spectrometry of each solid obtained, peaks were observed at [ M + H + ] ═ 1137, 1131, and 1041, respectively.

Synthesis example 22 Synthesis of intermediate G-5

Intermediate G-2(26.9G) was produced by the same method as that for the synthesis of intermediate A-3 of Synthesis example 1, using intermediate A-1(25.0G) and intermediate G-1 described above.

Next, by a method similar to that for the synthesis of intermediate C-3 in Synthesis example 13, intermediate G-5(9.6G) was produced from intermediate G-2 (24.5G). MS: [ M + H + ] ═ 587

Synthesis examples 23 and 24 < Synthesis of Compounds G-P-1 and G-P-2>

Compounds G-P-1(4.6G) and G-P-2(4.3G) were prepared by the same method as that for the synthesis of Compound B-P-1 of Synthesis example 8, using intermediate G-5(3.5G) and intermediates A-21 and A-22 described above, respectively. As a result of mass spectrometry of each solid obtained, peaks were observed at [ M + H + ], 1009 and 1067, respectively.

Synthesis example 25 Synthesis of intermediate D-4

Intermediate D-4(9.0g) was produced from intermediate A-2(30.0g) by the same method as that for the synthesis of intermediate F-4 in Synthesis example 18. MS: [ M + H + ] -789

Synthesis examples 26 to 28 < Synthesis of Compounds D-P-1 to D-P-3>

Compounds D-P-1(2.4g), D-P-2(2.0g) and D-P-3(2.3g) were prepared in the same manner as for the synthesis of Compound A-P-1 of Synthesis example 3, using intermediate D-4(2.5g) and intermediates A-23 to A-25 described above, respectively. As a result of mass spectrometry of each solid obtained, peaks were observed at [ M + H + ] ═ 1206, 1111, and 1271, respectively.

Synthesis example 29 Synthesis of intermediate E-5

Intermediate E-5(11.3G) was produced from intermediate E-1(30.0G) by the same method as that for the synthesis of intermediate G-5 in Synthesis example 21. MS: [ M + H + ] ═ 719

Synthesis examples 30 to 33 < Synthesis of Compounds E-P-1 to E-P-4>

Each of the compounds E-P-1(2.2g), E-P-2(2.7g), E-P-3(3.2g) and E-P-4(1.7g) was prepared by a method similar to that for the synthesis of Compound A-P-1 of Synthesis example 3, using intermediate E-5(2.5g) and intermediates A-12, A-26 to A-28 described above, respectively. As a result of mass spectrometry of each solid obtained, peaks were observed at [ M + H + ] -897, 1255, 1362 and 893.

< Experimental example 1>

For the above compounds, energy levels of homo, lumo and singlet states and oscillator strength of singlet states (radiative transition probability, f) of molecules were calculated by TD-DFT (B3LYP) method/6-31G-basis group method. The calculation results are shown in table 1 below.

[ Table 1]

	Comparative example 1	Comparative example 2	Example 1
				Compound (I)	Compound X-1	Compound X-2	Compound B-P-4
HOMO	4.9	4.91	4.77
				LUMO	1.39	0.95	1.43
S1	2.97	3.45	2.86
				f	0.273	0.299	0.515

The radiation transition probability (f) is calculated by the following equation as a measure showing the fluorescence quantum efficiency. The greater the value of the radiation transition probability (f), the greater the luminous efficiency.

Strength of vibrator

V is in units of s^-1Frequency of (2)

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

The radiative transition probability (f) of comparative examples 1 and 2 gave very small values compared to the compounds B-P-4 of example 1, which would be predicted to result in very low efficiency of devices comprising compounds X-1 and X-2. Further, the emission wavelength can be predicted from the singlet energy value of the compound X-2, and since it is a very short wavelength compared to the compound B-P-4, it is expected that the efficiency of the device is very low when used as a blue light emitting dopant of the light emitting layer, and thus cannot be said as a proper blue light emitting dopant.

Therefore, the compound B-P-4 has higher luminous efficiency and the efficiency of the blue light-emitting device is improved as compared with the compounds X-1 and X-2.

< Experimental example 2>

The maximum light emission wavelengths of the above-mentioned compounds X-3, X-4, X-5 and B-P-2 were measured and shown in Table 2 below.

[ Table 2]

The measuring apparatus used for measuring the maximum emission wavelength was a JASCO FP-8600 fluorescence spectrophotometer.

The maximum emission wavelength can be obtained as follows.Dissolving the compound to be measured to 10 by taking toluene as a solvent^-5M concentration, thereby preparing a sample for measurement. The sample solution was put into a quartz cuvette and nitrogen (N) gas was used₂) Degassing is performed to remove oxygen in the solution, and then the fluorescence intensity and the maximum luminescence peak can be measured at room temperature (300K) using a measuring apparatus. In this case, the x-axis of the emission spectrum is the wavelength (. lamda., unit: nm), and the y-axis is the emission intensity.

The maximum emission peak of the compound B-P-2 represented by the above chemical formula 1 is within 440nm to 465nm, but the compounds of comparative examples 3 to 5 (not having the structure of Cy1 of the above chemical formula 1) are outside the above range. Therefore, when the maximum light emission wavelength of the compound represented by the above chemical formula 1 satisfies the range of 440nm to 465nm, it is used as a blue light emitting dopant of the light emitting layer, and the efficiency of the device can be improved.

< Experimental example 3>

Example 3.

Indium Tin Oxide (ITO) and a process for producing the sameThe glass substrate coated to a thin film thickness of (2) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode thus prepared, HAT was added toThe thickness of (3) was subjected to thermal vacuum evaporation to form a hole injection layer. On the hole injection layerAs the first hole transporting layer, the following compound HT-A was vacuum-evaporatedNext, as a second hole transport layer, the following compound HT-B was vapor-depositedVacuum evaporation was performed using BH-A as a host and a compound A-P-3 as a dopant at a weight ratio of 96:4 to formA thick light emitting layer.

N mutext, as a layer for simultaneously performing electron injection and electron transport, the following compound ET-A and the following compound Liq were vapor-deposited at a ratio of 1:1On which lithium fluoride (LiF) is successively addedThickness of aluminum andthe cathode is formed by vapor deposition to produce an organic light-emitting device.

In the above process, the evaporation speed of the organic material is maintainedLithium fluoride maintenance of cathodeDeposition rate of (3), aluminum maintenanceThe vapor deposition rate of (2), the degree of vacuum of which is maintained at 1X 10 during vapor deposition^-7To 5X 10^-8And supporting to thereby fabricate an organic light emitting device.

Examples 4 to 18 and comparative examples 6 to 8

An organic light-emitting device was produced in the same manner as in example 3, except that in example 3, the host and dopant compounds described in table 3 below were used as the light-emitting layer material.

Organic light emitting devices fabricated by the above examples 3 to 18 and comparative examples 6 to 8 were operated at 10mA/cm²The efficiency was measured at the current density of (2). The results are shown in table 3 below.

[ Table 3]

	Main body (luminous layer)	Dopant (luminescent layer)	Luminous efficiency (cd/A)
				Example 3	BH-A	A-P-3	5.0
Example 4	BH-A	B-P-5	4.7
				Example 5	BH-A	B-P-3	4.9
Example 6	BH-A	C-P-2	5.2
				Example 7	BH-A	D-P-1	5.3
Example 8	BH-A	G-P-2	5.1
				Example 9	BH-A	F-P-1	5.1
Example 10	BH-A	E-P-2	5.1
				Comparative example 6	BH-A	X-4	4.4
Example 11	BH-B	A-P-4	5.2
				Example 12	BH-B	D-P-3	4.7
Example 13	BH-B	G-P-1	4.6
				Example 14	BH-B	E-P-4	4.6
Comparative example 7	BH-B	X-4	4.3
				Example 15	BH-C	A-P-3	5.1
Example 16	BH-C	C-P-2	5.4
				Example 17	BH-C	G-P-1	4.7
Example 18	BH-C	F-P-3	4.6
				Comparative example 8	BH-C	X-3	3.6

As shown in table 3 above, it is understood that the organic light emitting devices of examples 3 to 18, which include the compound of the present invention as a dopant of the light emitting layer, are superior in light emitting efficiency as compared to the organic light emitting devices of comparative examples 6 to 8. Specifically, as shown in the above comparative examples 3 and 4, the compounds X-3 and X-4 of the comparative examples have no ring of Cy1 of chemical formula 1, and thus the luminous efficiency is decreased.

Examples 19 to 31 and comparative examples 9 to 12

In the above example 3, as the host substance of the light emitting layer, the first host substance, the second host substance and the dopant were used in a weight ratio of 48: 4 toVacuum evaporation is performed to a thickness of (1). An organic light-emitting device was produced in the same manner as in example 3, except that the host and dopant compounds described in table 4 below were used as the light-emitting layer material.

Organic light emitting devices fabricated by the above examples 19 to 29 and comparative examples 9 to 12 were operated at 10mA/cm²The drive voltage and efficiency were measured at the current density of (2). The results are shown in table 4 below.

[ Table 4]

As shown in table 4 above, it is understood that the organic light emitting devices of examples 19 to 31, which include the compound of the present invention as a dopant of the light emitting layer, are excellent in light emitting efficiency and low in driving voltage as compared with the organic light emitting devices of comparative examples 9 to 12. Specifically, as shown in the above comparative examples 3 and 4, the compounds X-3 and X-4 of the comparative examples have no ring of Cy1 of chemical formula 1, and thus the luminous efficiency is decreased.