KR20220041531A - Compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification relates to a compound of chemical formula 1 and an organic light emitting device including the same. The compound described in the present specification can be used as a material for an organic material layer of the organic light emitting device. The compound according to another exemplary embodiment can improve efficiency, driving voltage, and lifespan characteristics in the organic light emitting device.

Description

Compound and organic light emitting device comprising the same

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.

The development of new materials for the organic light emitting device as described above is continuously required.

Korean Patent Publication No. 2000-0051826

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

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

[Formula 1]

In Formula 1,

X1 is O or S;

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

n1 is an integer from 0 to 8,

L1 is a direct bond; a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group,

L2 is a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group,

R100 to R104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r100 is an integer of 1 to 4, and when r100 is 2 or more, R100 of 2 or more are the same as or different from each other,

r101 is an integer of 1 to 3, and when r101 is 2 or more, R101 of 2 or more are the same as or different from each other,

r102 is an integer of 1 to 4, and when r102 is 2 or more, R102 of 2 or more are the same as or different from each other,

r103 is an integer of 1 to 2, and when r103 is 2 or more, R103 of 2 or more are the same as or different from each other,

r104 is an integer of 1 to 4, and when r104 is 2 or more, R104 of 2 or more are the same as or different from each other,

3 ≤ r102 + r103 + r104 ≤ 9.

In addition, the present specification is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one organic material layer includes the compound.

The compound described herein may be used as a material for an organic layer of an organic light emitting device. The compound according to another exemplary embodiment may improve efficiency, driving voltage, and lifespan characteristics in an organic light emitting diode.

1 and 2 show an example of an organic light emitting device according to an exemplary embodiment of the present specification.

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

An exemplary embodiment of the present specification provides a compound represented by Formula 1 above.

Formula 1 according to an exemplary embodiment of the present specification introduces a fluorene group substituted with R1 and R2 to have an effect of reducing the driving voltage of the organic light emitting device according to the improvement of the hole transport ability, and thus has excellent electron transport ability, high Naphthobenzofuran or naphthobenzothiophene having quantum efficiency is introduced through L2 to further reduce the driving voltage and improve efficiency.

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

는 연결되는 부위를 의미한다.In this specification,

means the part to be connected.

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; hydroxyl group; cyano group; nitro group; an alkyl group; cycloalkyl group; alkoxy group; alkenyl group; haloalkyl group; silyl group; boron group; amine group; aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.

또는

의 치환기가 될 수 있다. 또한, 3개의 치환기가 연결되는 것은 (치환기 1)-(치환기 2)-(치환기 3)이 연속하여 연결되는 것뿐만 아니라, (치환기 1)에 (치환기 2) 및 (치환기 3)이 연결되는 것도 포함한다. 예컨대, 페닐기, 나프틸기 및 이소프로필기가 연결되어,

,

또는

의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 정의가 동일하게 적용된다.In the present specification, that two or more substituents are connected means that the hydrogen of any one substituent is connected with the other substituent. For example, when two substituents are connected, a phenyl group and a naphthyl group are connected.

or

It can be a substituent of In addition, when three substituents are connected, (substituent 1)-(substituent 2)-(substituent 3) is not only continuously connected, but also (substituent 2) and (substituent 3) are connected to (substituent 1) include For example, a phenyl group, a naphthyl group and an isopropyl group are connected,

,

or

It can be a substituent of The above definition applies equally to a case in which 4 or more substituents are connected.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, There are 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and adamantyl groups. , but is not limited thereto.

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

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but is not limited thereto.

In the present specification, the haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, and the like, but is not limited thereto.

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

,

,

,

,

,

,

및

등이 있으나, 이에 한정되지 않는다.When the fluorene group is substituted,

,

,

,

,

,

,

and

and the like, but is not limited thereto.

As used herein, the "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. can For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group. , pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group (phenoxathiine), phenoxazine group (phenoxazine), phenothiazine group (phenothiazine), dihydroindenocarbazole group, spirofluorene xanthene group and spirofluorene There is a thioxanthene group, but is not limited thereto.

In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, or the like. Examples of the above-described alkyl group may be applied to the alkyl group of the alkylsilyl group, the examples of the above-described aryl group may be applied to the aryl group of the arylsilyl group, and the heteroaryl group of the heteroarylsilyl group is an example of the heteroaryl group. can be applied.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. Specifically, 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 amine group is -NH ₂ , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group from the group consisting of may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group. , diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthre There is a nylfluorenylamine group, an N-biphenylfluorenylamine group, and the like, but is not limited thereto.

In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group. The alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.

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

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

In the present specification, examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group. The alkyl group in the alkylamine group may be a straight-chain or branched alkyl group. The alkylamine group including two or more alkyl groups may include a straight-chain alkyl group, a branched-chain alkyl group, or a straight-chain alkyl group and a branched alkyl group at the same time. For example, the alkyl group in the alkylamine group may be selected from the examples of the alkyl group described above.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

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

In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.

Unless defined otherwise herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned in this specification are incorporated herein by reference in their entirety, and in the event of a conflict the present specification, including definitions, will control unless a specific passage is recited. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.

According to an exemplary embodiment of the present specification, R100 is hydrogen.

According to an exemplary embodiment of the present specification, R101 is hydrogen.

According to an exemplary embodiment of the present specification, R102 is hydrogen.

According to an exemplary embodiment of the present specification, R103 is hydrogen.

According to an exemplary embodiment of the present specification, R104 is hydrogen.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

The definitions of X1, R1, R2, L1, L2 and n1 are the same as those defined in Formula 1 above.

According to an exemplary embodiment of the present specification, X1 is O.

According to an exemplary embodiment of the present specification, X1 is S.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formulas 1-4 to 1-9.

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

In Formulas 1-4 to 1-9,

The definitions of R1, R2, L1, L2 and n1 are the same as those defined in Formula 1 above.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted C1-C30 linear or branched alkyl group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently an alkyl group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 are methyl groups.

According to an exemplary embodiment of the present specification, L1 is a direct bond; phenylene group; or a naphthylene group.

According to an exemplary embodiment of the present specification, L2 is a phenylene group; or a naphthylene group.

According to an exemplary embodiment of the present specification, X1 is O or S, wherein R1 and R2 are the same as or different from each other, and each independently represent a linear or branched alkyl group having 1 to 30 carbon atoms, and L1 is a direct bond; phenylene group; or a naphthylene group, wherein L2 is a phenylene group; or a naphthylene group.

According to an exemplary embodiment of the present specification, Formula 1 is any one selected from the following compounds.

.

.

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

In the present specification, when a member is said to be located “on” another member, this includes not only a case in which a member is in contact with another member but also a case in which another member is present between the two members.

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

In the present specification, the 'layer' means compatible with a 'film' mainly used in the present technical field, and refers to a coating covering a desired area. The size of the 'layers' is not limited, and each of the 'layers' may have the same size or different sizes. According to an exemplary embodiment, the size of the 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.

In the present specification, the meaning that a specific material A is included in layer B means that i) one or more types of material A are included in one layer B, and ii) layer B is composed of one or more layers, and material A is multi-layered B. It includes everything included in one or more floors among the floors.

In the present specification, the meaning that a specific material A is included in the C layer or the D layer means i) is included in one or more of the one or more layers C, ii) is included in one or more of the one or more layers of the D layer, or iii ) means all of which are included in one or more layers C and one or more layers D, respectively.

The present specification includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. do.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

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

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

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

According to an exemplary embodiment of the present specification, the emission layer includes a dopant, and the dopant includes at least one of a fluorescent dopant, a phosphorescent dopant, and a thermally delayed fluorescence-based dopant.

According to an exemplary embodiment of the present specification, the fluorescent dopant includes at least one of an arylamine-based compound and a boron-based compound.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, the emission layer includes a host and a dopant, the host includes the compound, and the dopant includes the fluorescent dopant, phosphorescent dopant, and thermally delayed fluorescence. at least one of the dopants.

According to an exemplary embodiment of the present specification, the arylamine-based compound is represented by the following Chemical Formula D-1.

[Formula D-1]

In the formula D-1,

L101 and L102 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar101 to Ar104 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, L101 and L102 are a direct bond.

According to an exemplary embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl having 6 to 30 carbon atoms, unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms. energy; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and each independently a phenyl group substituted with a methyl group; or a dibenzofuran group.

According to an exemplary embodiment of the present specification, Formula D-1 is represented by the following compound.

According to an exemplary embodiment of the present specification, the boron-based compound is represented by the following Chemical Formula D-2.

[Formula D-2]

In Formula D-2,

T1 to T5 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; Or a substituted or unsubstituted aryl group,

t3 and t4 are each an integer of 1 to 4,

t5 is an integer from 1 to 3;

When t3 is 2 or more, the 2 or more T3 are the same as or different from each other,

When t4 is 2 or more, the 2 or more T4 are the same as or different from each other,

When t5 is 2 or more, the 2 or more T5s are the same as or different from each other.

According to an exemplary embodiment of the present specification, the T1 to T5 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the T1 to T5 are the same as or different from each other, and each independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the T1 to T5 are the same as or different from each other, and each independently hydrogen; tert-butyl group; diphenylamine group; or a phenyl group unsubstituted or substituted with a tert-butyl group.

According to an exemplary embodiment of the present specification, Formula D-2 is represented by the following compound.

According to an exemplary embodiment of the present specification, the light emitting layer includes a host and a dopant in a weight ratio of 99:1 to 30:70.

As the phosphorescent dopant and the thermally delayed fluorescence dopant, a conventionally known material may be used, but the present invention is not limited thereto.

According to an exemplary embodiment of the present specification, the organic light emitting device includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer. include more

According to an exemplary embodiment of the present specification, the organic light emitting device includes a first electrode; a second electrode provided to face the first electrode; a light emitting layer provided between the first electrode and the second electrode; and two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode.

According to an exemplary embodiment of the present specification, two or more organic material layers between the light emitting layer and the first electrode or between the light emitting layer and the second electrode are a light emitting layer, a hole transport layer, a hole injection layer, a hole injection and transport layer, an electron blocking layer , at least two may be selected from the group consisting of a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.

According to an exemplary embodiment of the present specification, two or more hole transport layers are included between the light emitting layer and the first electrode. The two or more hole transport layers may include the same or different materials.

According to an exemplary embodiment of the present specification, the first electrode is an anode or a cathode.

According to an exemplary embodiment of the present specification, the second electrode is a negative electrode or a positive electrode.

According to an exemplary embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

According to an exemplary embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

For example, the structure of the organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2 . 1 and 2 illustrate an organic light emitting device, but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which a first electrode 2 , a light emitting layer 4 , and a second electrode 3 are sequentially stacked on a substrate 1 . The compound is included in the light emitting layer.

2 shows a first electrode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, a light emitting layer 4, an electron transport layer 8, electrons on the substrate 1 The structure of the organic light emitting device in which the injection layer 9 and the second electrode 3 are sequentially stacked is illustrated. The compound of Formula 1 is included in the emission layer.

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that the light emitting layer includes the compound, that is, the compound represented by Formula 1 above.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form the anode. It can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.

In addition, the compound represented by Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and a first electrode material on a substrate from the second electrode material. However, the manufacturing method is not limited thereto.

As the material for the first electrode, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : a combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The second electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. metals or alloys thereof such as, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; LiF/Al or a multi-layered material such as LiO ₂ /Al, but is not limited thereto.

The emission layer may include a host material and a dopant material. When an additional light emitting layer is included in addition to the light emitting layer including the compound represented by Formula 1 according to an exemplary embodiment of the present specification, the host material may include a condensed and/or non-condensed aromatic ring derivative or a hetero ring containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periplanthene, and the like, having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group A substituent is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injecting material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injecting effect for the light emitting layer or the light emitting material. In addition, a material excellent in the ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in the ability to form a thin film is preferable. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material, metal porphyrin (porphyrin), oligothiophene, arylamine-based organic material; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic substances; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer, and a material having high hole mobility is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transport material is a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material, as used in accordance with the prior art. In particular, suitable cathode materials are conventional materials having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium, samarium, and the like, followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injecting material has excellent electron transport ability and has an electron receiving effect from the second electrode and an excellent electron injecting effect with respect to the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof; metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

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

The electron blocking layer is a layer capable of improving the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the emission layer. A known material can be used without limitation, and may be formed between the light emitting layer and the hole injection layer, between the light emitting layer and the hole transport layer, or between the light emitting layer and the layer that simultaneously injects and transports holes.

The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but is not limited thereto.

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

Hereinafter, in order to describe the present specification in detail, it will be described in detail with reference to Examples and Comparative Examples. However, the Examples and Comparative Examples according to the present specification may be modified in various other forms, and the scope of the present specification is not to be construed as being limited to the Examples and Comparative Examples described below. Examples and comparative examples of the present specification are provided to more completely explain the present specification to those of ordinary skill in the art.

Preparation Example 1. Preparation of compound BH-1

Preparation Example 1-1) Preparation of compound BH-1-1

In a 3-neck flask, dissolve 9-bromoanthracene (50.0 g, 194 mmol), (9,9-dimethyl-9H-fluoren-4-yl) boronic acid (45.3 g, 214 mmol) in 500 ml of 1,4-dioxane, K ₂ CO ₃ (80.6 g, 583 mmol) was dissolved in H ₂ O 200ml. Pd(P(t-Bu) ₃ ) ₂ (1.98 g, 3.9 mmol) was added thereto, and the mixture was stirred for 5 hours under reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and toluene. After drying the extract with MgSO ₄ , filtration and concentration, the sample was purified by silica gel column chromatography to obtain 50.2 g of compound BH-1-1. (Yield 70%, MS[M+H]+=371)

Preparation Example 1-2) Preparation of compound BH-1-2

Compound BH-1-1 (20.0g, 58.1mmol), N-bromosuccinimide (NBS) (11.4g, 63.9mmol), and dimethylformamide (DMF) 300ml were placed in a two-necked flask at room temperature under an argon atmosphere. was stirred for 10 hours. After completion of the reaction, the reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 19.1 g of compound BH-1-2. (yield 79%, MS[M+H]+=450)

Preparation Example 1-3) Preparation of compound BH-1

Compound BH-1-2 (20.0g, 44.5mmol), (4-(naphtho[2,3-b]benzofuran-2-yl)phenyl)boronic acid (16.6g, 49.0mmol) 1, Dissolved in 300 ml of 4-dioxane, K ₂ CO ₃ (13.1 g, 94.5 mmol) was dissolved in H 2 O 100 ml. Pd(P(t-Bu) ₃ ) ₂ (0.47 g, 0.47 mmol) was added thereto, and the mixture was stirred for 5 hours under reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and toluene. After drying the extract with MgSO ₄ , filtration and concentration, the sample was purified by silica gel column chromatography to obtain 14.6 g of compound BH-1. (Yield 35%, MS[M+H]+=663)

Preparation Example 2. Preparation of compound BH-2

Preparation Example 2-1) Preparation of compound BH-2-1

The same method as in Preparation Example 1-1 was used except that (9,9-dimethyl-9H-fluoren-3-yl)boronic acid was used instead of (9,9-dimethyl-9H-fluoren-4-yl)boronic acid. 50.8 g of compound BH-2-1 was obtained. (Yield 71%, MS[M+H]+=371)

Preparation Example 2-2) Preparation of compound BH-2-2

18.7 g of compound BH-2-2 was obtained in the same manner as in Preparation Example 1-2, except that BH-2-1 was used instead of BH-1-1. (Yield 77%, MS[M+H]+=450)

Preparation Example 2-3) Preparation of compound BH-2

Except for using (4-(naphtho[1,2-b]benzofuran-7-yl)phenyl)boronic acid instead of (4-(naphtho[2,3-b]benzofuran-2-yl)phenyl)boronic acid, 12.1 g of compound BH-2 was obtained in the same manner as in Preparation Example 1-3. (Yield 29%, MS[M+H]+=663)

Preparation Example 3. Preparation of compound BH-3

Except for using (4-(naphtho[2,1-b]benzofuran-10-yl)phenyl)boronic acid instead of (4-(naphtho[1,2-b]benzofuran-7-yl)phenyl)boronic acid, 15.5 g of compound BH-3 was obtained in the same manner as in Preparation Example 2-3. (Yield 37%, MS[M+H]+=663)

Preparation Example 4. Preparation of compound BH-4

Except for using (3-(naphtho[2,3-b]benzofuran-1-yl)phenyl)boronic acid instead of (4-(naphtho[2,3-b]benzofuran-2-yl)phenyl)boronic acid, 16.0 g of compound BH-4 was obtained in the same manner as in Preparation Example 1-3. (Yield 38%, MS[M+H]+=663)

Preparation 5. Preparation of compound BH-5

Preparation Example 5-1) Preparation of compound BH-5-1

The same method as in Preparation Example 1-1 was used except that (9,9-dimethyl-9H-fluoren-2-yl)boronic acid was used instead of (9,9-dimethyl-9H-fluoren-4-yl)boronic acid. 53.8 g of compound BH-5-1 was obtained. (yield 76%, MS[M+H]+=371)

Preparation Example 5-2) Preparation of compound BH-5-2

19.3 g of compound BH-5-2 was obtained in the same manner as in Preparation Example 1-2, except that BH-5-1 was used instead of BH-1-1. (yield 79%, MS[M+H]+=450)

Preparation Example 5-3) Preparation of compound BH-5

16.9 g of compound BH-5 was obtained in the same manner as in Preparation Example 1-3, except that BH-5-2 was used instead of BH-1-2. (Yield 41%, MS[M+H]+=663)

Preparation Example 6. Preparation of compound BH-6

Preparation Example 6-1) Preparation of compound BH-6-1

The same method as in Preparation Example 1-1 was used except that (9,9-dimethyl-9H-fluoren-1-yl)boronic acid was used instead of (9,9-dimethyl-9H-fluoren-4-yl)boronic acid. 51.1 g of compound BH-6-1 was obtained. (Yield 72%, MS[M+H]+=371)

Preparation Example 6-2) Preparation of compound BH-6-2

18.8 g of compound BH-6-2 was obtained in the same manner as in Preparation Example 1-2, except that BH-6-1 was used instead of BH-1-1. (Yield 77%, MS[M+H]+=450)

Preparation Example 6-3) Preparation of compound BH-6

14.1 g of compound BH-6 was obtained in the same manner as in Preparation Example 1-3, except that BH-6-2 was used instead of BH-1-2. (Yield 34%, MS[M+H]+=663)

Preparation Example 7. Preparation of compound BH-7

18.0 g of compound BH-7 was obtained in the same manner as in Preparation Example 1-3, except that BH-5-2 was used instead of BH-1-2. (Yield 41%, MS[M+H]+=713)

[Example]

Example 1

A glass substrate coated with a thin film of ITO (Indium Tin Oxide) with a thickness of 150 nm was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. In this case, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using nitrogen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, the following HAT-CN compound was thermally vacuum deposited to a thickness of 5 nm to form a hole injection layer. Subsequently, HTL1 was thermally vacuum deposited to a thickness of 100 nm to form a first hole transport layer, and then HTL2 was thermally vacuum deposited to a thickness of 10 nm to form a second hole transport layer. Then, the following compound BD as a dopant and compound BH-1 (weight ratio 5:95) as a host were simultaneously vacuum-deposited to form a light emitting layer with a thickness of 20 nm. Then, ETL was vacuum-deposited to a thickness of 20 nm to form an electron transport layer. Then, LiF was vacuum-deposited to a thickness of 0.5 nm to form an electron injection layer. Then, aluminum was deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic light emitting diode.

In the above process, the deposition rate of the organic material was maintained at 0.04 to 0.09 nm/sec, the lithium fluoride of the electron transport layer was maintained at 0.03 nm/sec, and the aluminum of the cathode was 0.2 nm/sec. By maintaining 1×10 ^-7 to 5×10 ^-5 torr, an organic light emitting device was manufactured.

Examples 2 to 7

An organic light emitting diode was manufactured in the same manner as in Example 1, except that in Example 1, compounds BH-2 to BH-7 were used instead of BH-1 as the host compound of the light emitting layer, respectively.

Comparative Examples 1 to 4

An organic light emitting diode was manufactured in the same manner as in Example 1, except that in Example 1, compounds BH-A to BH-D were used instead of BH-1 as the host compound of the emission layer. Compounds BH-A to BH-D are as follows, respectively.

For the organic light emitting diodes prepared in Examples 1 to 7 and Comparative Examples 1 to 4, the driving voltage and luminous efficiency were measured at a current density of 10 mA/cm ² , and compared to the initial luminance at a current density of 20 mA/cm ² The time to 97% (T ₉₇ ) was measured. The results are shown in Table 1 below.

host
compound 10 mA/cm ² measured value life span
(T ₉₇ ) drive voltage
(V _OP ) luminous efficiency
(Cd/A) color coordinates CIE_x CIE_y Example 1 BH-1 3.38 8.50 0.137 0.119 160 Example 2 BH-2 3.40 8.55 0.137 0.118 155 Example 3 BH-3 3.35 8.45 0.138 0.118 155 Example 4 BH-4 3.42 8.58 0.138 0.119 160 Example 5 BH-5 3.40 8.51 0.137 0.118 150 Example 6 BH-6 3.38 8.48 0.138 0.118 155 Example 7 BH-7 3.38 8.53 0.138 0.118 155 Comparative Example 1 BH-A 3.60 8.20 0.138 0.118 70 Comparative Example 2 BH-B 3.65 8.25 0.138 0.119 75 Comparative Example 3 BH-C 3.67 8.23 0.138 0.118 70 Comparative Example 4 BH-D 3.60 8.28 0.138 0.118 60

In Table 1, the organic light emitting devices of Examples 1 to 7 using the compound of Formula 1 according to an exemplary embodiment of the present specification have a lower voltage than Comparative Examples 1 to 4 using the compound in which L2 of Formula 1 is a direct bond. , it can be seen that it has the characteristics of high efficiency and long life.

1: Substrate
2: first electrode
3: second electrode
4: light emitting layer
5: hole injection layer
6: first hole transport layer
7: second hole transport layer
8: electron transport layer
9: electron injection layer

Claims (10)

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

In Formula 1,
X1 is O or S;
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
n1 is an integer from 0 to 8,
L1 is a direct bond; a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group,
L2 is a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group,
R100 to R104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r100 is an integer of 1 to 4, and when r100 is 2 or more, R100 of 2 or more are the same as or different from each other,
r101 is an integer of 1 to 3, and when r101 is 2 or more, R101 of 2 or more are the same as or different from each other,
r102 is an integer of 1 to 4, and when r102 is 2 or more, R102 of 2 or more are the same as or different from each other,
r103 is an integer of 1 to 2, and when r103 is 2 or more, R103 of 2 or more are the same as or different from each other,
r104 is an integer of 1 to 4, and when r104 is 2 or more, R104 of 2 or more are the same as or different from each other,
3 ≤ r102 + r103 + r104 ≤ 9. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,
The definitions of X1, R1, R2, L1, L2 and n1 are the same as those defined in Formula 1 above. The method according to claim 1, wherein Chemical Formula 1 is a compound represented by the following Chemical Formulas 1-4 to 1-9:
[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

In Formulas 1-4 to 1-9,
The definitions of R1, R2, L1, L2 and n1 are the same as those defined in Formula 1 above. The method according to claim 1, wherein X1 is O or S,
Wherein R1 and R2 are the same as or different from each other, and each independently represent a linear or branched alkyl group having 1 to 30 carbon atoms,
The L1 is a direct bond; phenylene group; or a naphthylene group,
L2 is a phenylene group; or a naphthylene group. The compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:

. a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound of any one of claims 1 to 5. The organic light emitting device of claim 6 , wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the compound. The organic light-emitting device of claim 6 , wherein the organic material layer includes an emission layer, and the emission layer includes the compound as a host of the emission layer. The organic light-emitting device of claim 8 , wherein the emission layer includes a dopant, and the dopant includes at least one of a fluorescent dopant, a phosphorescent dopant, and a thermally delayed fluorescence-based dopant. The organic light-emitting device of claim 9 , wherein the fluorescent dopant includes at least one arylamine-based compound and one or more boron-based compounds.

Images