KR20190034095A - Delayed fluorescence material and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a delayed fluorescent material and an organic light emitting device including the same. The delayed fluorescence material of the present invention comprises a compound represented by chemical formula 1. In chemical formula 1, R1 and R2 are the same or different, and are each independently an aryl group, and R3 is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. According to the present invention, the organic light emitting device using the delayed fluorescent material can improve efficiency and low driving voltage and/or lifespan characteristics.

Description

TECHNICAL FIELD [0001] The present invention relates to a retardation fluorescent material and an organic light emitting device including the retardation fluorescent material.

This application claims the benefit of Korean Patent Application No. 10- 2017-0122405, filed on September 22, 2017, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a retardation fluorescent material and an organic light emitting device including the same.

In order to commercialize an organic light emitting device, it is necessary to improve the efficiency of a light emitting material. For this purpose, studies on phosphorescent and retarding fluorescent materials have been actively conducted. However, in the case of the above-mentioned phosphorescent material, there is a problem that the cost of the metal complex required to realize phosphorescence is high and the lifetime is short, although high efficiency can be achieved.

Recently, the introduction of the concept of thermally activated delayed fluorescence (TADF) in the case of the retarded fluorescent material has revealed a highly efficient green fluorescent material having a high external quantum efficiency as well as a fluorescent material. The concept of thermally activated delayed fluorescence (TADF) is a phenomenon in which the inverse energy transfer from the excited triplet state to the excited singlet state is caused by thermal activation, leading to fluorescence emission. Generally, the lifetime It is called delayed fluorescence in that long luminescence occurs. Since the retardation fluorescent material can use both fluorescence emission and phosphorescence emission, the problem of the cost of the phosphorescent material can be solved in that the problem of the external quantum efficiency of the conventional fluorescent material can be solved and the metal complex is not required.

Nature, 492, pp 234-238 J. Am. Chem. Soc., 2012, 134 (36), pp 14706-14709

The present invention provides a retardation fluorescent material and an organic light emitting device including the same.

According to one embodiment of the present invention, there is provided a retardation fluorescent material comprising a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R1 and R2 are the same or different and are each independently an aryl group,

R3 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R11 to R13 and R111 to R113 are the same or different and are each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

n1, m1 and m11 are each 0 or 1,

r3, r11 to r13 and r111 to r113 are each an integer of 1 to 4,

When r3, r11 to r13 and r111 to r113 are respectively 2 or more, the structures in parentheses of 2 or more are the same or different from each other.

According to an embodiment of the present invention, there is also provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the retarded fluorescent material.

An organic light emitting device using a retardation fluorescent material composed of a compound represented by Chemical Formula 1 according to one embodiment of the present invention can improve efficiency, improve driving voltage and / or lifetime characteristics.

1 shows an organic light emitting device according to an embodiment of the present invention.
Figure 2 is a MS graph of Compound 1 according to one embodiment of the present disclosure;
3 is a graph showing the UV-vis absorption spectrum of Compound 1 according to one embodiment of the present invention, the photoluminescence spectrum at a solution state (toluene or tetrahydrofuran (THF)) and the photoluminescence spectrum at a low- to be.

According to one embodiment of the present invention, there is provided a retardation fluorescent material comprising a compound represented by the above formula (1).

The compound represented by Chemical Formula (1) according to one embodiment of the present invention includes a triazine group serving as an electron acceptor to facilitate electron injection, and an organic light emitting device using the same as a retardation fluorescent material has characteristics of high efficiency and long life.

In addition, the compound represented by Formula 1 has a phenylene group as a linker between each triazine group and a phenylene group as a linker between a triazine group and a carbazole group to enhance the cell injection property and use it as a light emitting layer The efficiency of the organic light emitting device can be improved.

Herein delayed fluorescence is meant that the exciton emits fluorescent light in the triplet excited state (T ₁₎ the singlet excited state (S ₁₎ conversion (converting) to be a singlet excited state (S ₁₎ from. Delayed fluorescence is distinguished from fluorescence in that the peak position of the luminescence spectrum is the same as that of fluorescence but is long in decay time. The decay time is long, but the peak position of the luminescence spectrum differs from the fluorescence spectrum by the difference of S ₁ -T ₁ energy It differs from phosphorescence in that it is different.

According to one embodiment of the present invention, the compound represented by Formula (1) includes a phenylene group as a linker between each triazine group and a phenylene group as a linker between the triazine group and the carbazole group, The energy difference between the central state and the triplet state can be appropriately controlled. Through this, it is possible to exhibit thermally activated delayed fluorescence (TADF).

According to one embodiment of the present invention, the triplet energy level of the compound represented by Formula 1 is 2.0 eV or more, specifically 2.0 eV or more and 3 eV or less, more specifically 2.4 eV or more and 2.9 eV or less to be. When the triplet energy level satisfies the above range, an organic light emitting device having a low driving voltage, a long lifetime, and excellent luminous efficiency can be realized.

According to one embodiment of the present invention, the difference between the singlet energy level and the triplet energy level of the compound represented by Formula 1 is 0.3 eV or less, specifically 0.25 eV or less and 0.01 eV or more, Specifically, it is 0.2 eV or less and 0.03 eV or more. The difference between the singlet energy level and the triplet energy level means the absolute value of the singlet energy level to the triplet energy level. When the difference between the singlet energy level and the triplet energy level satisfies the above range, it is possible to effectively block the orbital overlap in the molecule and prevent the singlet and triplet from overlapping, And may have the difference value. This makes it possible to transition from a triplet excited state to a singly excited state through thermal activation even at room temperature, thereby exhibiting delayed fluorescence.

The triplet energy level and singlet energy level can be measured using methods known in the art, but are not limited thereto.

In this specification, when a part is referred to as " including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

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

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

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, " a substituent to which at least two substituents are connected " may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with an ester group oxygen in a straight chain, branched chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, 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 may be monocyclic or polycyclic, and is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3- Dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclopentylcyclohexyl, cyclohexylcyclohexyl, And the like, but the present invention is not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n Butyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like. But is not limited thereto.

In this specification, the amine group is -NH ₂ ; An alkylamine group; N-alkylarylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, Phenylnaphthylenediamine group, N-phenylphenylenediamine group, N-phenyltriphenylamine group, N-phenylphenanthrenylamine group, N-phenylphenanthrenylamine group, Group, an N-phenanthrenylfluorenylamine group, and an N-biphenylfluorenylamine group, but the present invention is not limited thereto.

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

In the present specification, the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.

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

In the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine group is the same as the alkyl group described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, And the like, but the present invention is not limited thereto.

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, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, However, the present invention is not limited thereto.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but is not limited thereto.

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 is preferably 6 to 30 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl, , But is not limited thereto.

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

,

,

,

,

및

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

,

,

,

,

And

And the like. However, the present invention is not limited thereto.

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

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group. However, the present invention is not limited thereto.

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 having at least two aryl groups may contain 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, the heteroaryl group includes at least one non-carbon atom and at least one hetero atom. Specifically, the hetero atom 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 is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, , An isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, Phenanthroline, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but the present invention is not limited thereto.

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 having 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 above-mentioned heteroaryl group.

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

According to one embodiment of the present invention, the formula (1) is represented by the following formula (1-1).

[Formula 1-1]

In Formula 1-1,

R1 and R2 are the same or different and are each independently an aryl group,

R11, R12, R111 and R112 are the same or different and are each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r11, r12, r111 and r112 are each an integer of 1 to 4,

When r11, r12, r111 and r112 are two or more, the structures in the parentheses of two or more are the same or different.

According to one embodiment of the present invention, in the general formula (1), R 1 and R 2 are the same or different from each other, and are each independently a phenyl group; Or a biphenyl group.

According to one embodiment of the present invention, in the general formula (1), R 1 and R 2 are the same or different from each other, and are each independently a phenyl group; A 2-biphenyl group; 3-biphenyl group; Or a 4-biphenyl group.

According to an embodiment of the present invention, R11, R12, R111 and R112 are the same or different from each other, and each independently hydrogen; Or an alkyl group.

According to an embodiment of the present invention, R11, R12, R111 and R112 are the same or different from each other, and each independently hydrogen; Methyl group; Or a t-butyl group.

According to one embodiment of the present disclosure, Formula 1 is selected from the following compounds.

According to one embodiment of the present invention, there is provided an organic light emitting device comprising a retardation fluorescent material comprising a compound represented by Formula 1.

According to one embodiment of the present disclosure, there is provided a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the above-described retardation fluorescent material.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.

For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.

1 illustrates a structure of an organic light emitting diode 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. 1 is an exemplary structure of an organic light emitting diode according to an embodiment of the present invention, and may further include another organic layer.

According to an embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the retardation fluorescent material described above.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the above-described retarding fluorescent material as a dopant of the light emitting layer.

According to one embodiment of the present invention, the light emitting material of the light emitting layer is a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, At least one of the excitation light energy and the excitation triplet energy has a higher value than that of the light emitting material of the retardation fluorescent material and has a hole transporting ability and an electron transporting ability, Can be prevented, and an organic compound having a high glass transition temperature can be included as a host.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a host.

According to an embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes at least one selected from the following Formulas A to F as a host of the light emitting layer.

(A)

In the above formula (A)

Y1 is NR ', S or O,

q1 is an integer of 0 to 3,

R 'is an alkyl group; Or an aryl group,

[Chemical Formula B]

In the above formula (B)

Y2 is O or S,

L1 is a biphenyllylene group; A fluorenylene group substituted or unsubstituted with an alkyl group or an aryl group; Or a spirobifluorenylene group,

A 1 is an alkyl group, a silyl group substituted with an alkyl group, or a carbazolyl group substituted or unsubstituted with an aryl group,

≪ RTI ID = 0.0 &

In the above formula (C)

Q1 to Q8 are the same or different from each other, and each independently hydrogen; An aryl group substituted or unsubstituted with a heteroaryl group; Or a heteroaryl group, or adjacent groups may combine with each other to form a heterocyclic ring which is substituted or unsubstituted with an aryl group or a heteroaryl group,

[Chemical Formula D]

(E)

[Chemical Formula F]

In Formula (F) above,

Y3 is a direct bond; Or O,

Q9 and Q10 are the same or different from each other, and each independently hydrogen; Or a heteroaryl group substituted with an aryl group,

q9 and q10 are each an integer of 1 to 4,

q11 is 1 or 2,

When q9 and q10 are each 2 or more, the structures in parentheses of 2 or more are the same or different from each other.

According to an embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a dopant and a host in a weight ratio of 1:99 to 10:90.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer comprises a dopant including the retardation fluorescent material described above, and a host comprising at least one selected from the following formulas A to F, 10:90 by weight.

According to one embodiment of the present invention, in Formula (B), L1 is any one selected from the following structures.

According to one embodiment of the present invention, in the above formula (B), A1 is represented by the following structure.

In the above structure,

A2 and A3 are the same or different from each other, and each independently hydrogen; An alkyl group; A silyl group substituted with an alkyl group; Or an aryl group,

o and p are each an integer of 1 to 4,

When o and p are each 2 or more, the structures in parentheses of 2 or more are the same or different from each other.

According to another embodiment of the present invention, A2 and A3 are the same or different from each other, and each independently hydrogen; Methyl group; t-butyl group; A trimethylsilyl group; A phenyl group; Or a biphenyl group.

According to one embodiment of the present invention, in the above formula (C), Q1 to Q8 are the same or different and each independently hydrogen; A phenyl group substituted or unsubstituted with a carbazolyl group or a dibenzofurane group; A biphenyl group; A terphenyl group; Or a carbazolyl group.

According to one embodiment of the present invention, in the above formula (C), adjacent groups among Q1 to Q8 are bonded to each other to form a benzofuran ring which is substituted or unsubstituted with an aryl group or a heteroaryl group.

According to one embodiment of the present invention, in the above formula (C), adjacent groups of Q1 to Q8 are bonded to each other to form a benzofuran ring substituted or unsubstituted with a biphenyl group, a terphenyl group, or a carbazolyl group.

According to one embodiment of the present disclosure, the formula C is selected from the following compounds.

According to one embodiment of the present disclosure, the formula (D) is selected from the following compounds.

According to one embodiment of the present disclosure, in Formula F, Q9 and Q10 are the same or different from each other, and each independently hydrogen; Or a carbazolyl group substituted with a phenyl group.

According to one embodiment of the present specification, in the above formula (F), q11 is 1.

According to one embodiment of the present specification, in the above formula (F), q11 is 2.

According to one embodiment of the present disclosure, Formula F is selected from the following compounds.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer further includes a fluorescent dopant.

According to one embodiment of the present invention, the light emitting layer includes the retardation fluorescent material described above as a dopant, and includes at least any one of the above-described Formulas A to F as a host, and further includes a further fluorescent dopant.

The fluorescent dopant may be contained in an amount of 0.01 to 10 parts by weight, preferably 0.1 to 10 parts by weight, based on the entire light emitting layer.

According to one embodiment of the present invention, the fluorescent dopant includes at least one selected from the following formulas (G) and (H).

[Formula G]

[Formula H] <

In the above formulas G and H,

Ar1 to Ar4 and G1 to G4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

The organic luminescent device of the present invention includes a delayed fluorescent material of the present specification as the dopant of the light emitting layer, that is, a retardation fluorescent material composed of the compound represented by the above formula (1), and as a host of the luminescent layer, But may be made of materials and methods known in the art, except for including at least one selected.

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

For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming a first electrode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the first electrode, and depositing a material usable as a second electrode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. The heterocyclic compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of 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.

According to one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

According to another embodiment of the present invention, the first electrode is a cathode and the second electrode is a cathode.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode 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 oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

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

The hole injecting layer is a layer for injecting holes from the electrode as a hole injecting material and a hole injecting effect for injecting holes in the anode as a hole injecting material and an excellent hole injecting effect for a light emitting layer or a light emitting material , The migration of excitons generated in the light emitting layer to the electron injection layer or the electron injection material, and also the ability to form thin films is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The electron transporting material of the electron transporting layer is a layer that transports electrons from the electron injecting layer to the electron transporting layer and transports electrons from the cathode to the light emitting layer. This large material is suitable. 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 transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

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

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

Production Example 1. Preparation of Compound 1

(1) Preparation of intermediate 1-1

8.0 g (35.7 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine and 14.8 g (107.1 mmol) of potassium carbonate were dissolved in tetrahydrofuran was dissolved in a mixed solvent of 140 mL of distilled water and 70 mL, followed by the addition of _{Pd (PPh 3) 4 1.2 g} (1.07 mmol) was refluxed for 12 hours. After cooling to room temperature, the water layer was removed, and an anhydrous magnesium sulfate was added to the organic layer, followed by filtration. Concentrated and purified by column chromatography to obtain Intermediate 1-1 (7.7 g, yield 76%).

(2) Preparation of intermediate 1-2

7.7 g (27.01 mmol) of Intermediate 1-1, 2.24 g (13.5 mmol) of 1,4-phenylenediboronic acid and 5.6 g (40.5 mmol) of potassium carbonate were dissolved in a mixed solvent of 50 mL of tetrahydrofuran and 25 mL of distilled water, (PPh _{3) 4} followed by the addition of 0.5 g (0.4 mmol) was refluxed for 12 hours. After cooling to room temperature, the water layer was removed, and an anhydrous magnesium sulfate was added to the organic layer, followed by filtration. Concentrated and purified by column chromatography to obtain Intermediate 1-2 (6.3 g, yield 81%).

(3) Preparation of Compound 1

6.1 g (21.86 mmol) of 3,6-di-tert-butyl-9H-carbazole and 14.2 g (43.72 mmol) of cesium carbonate were added to Dimethylformamide (84 ml) Respectively. When the reaction was terminated, the reaction mixture was filtered through silica gel / celite, concentrated under reduced pressure, and separated into a column. The resulting solution was concentrated under reduced pressure, then crystallized with hexane and filtered to obtain Compound 1 (8.1 g, yield 68%).

MS [M + H] < ⁺ > = 1095

FIG. 2 is a graph showing an MS graph of the compound 1. FIG.

3 is a UV-vis absorption spectrum of compound 1 according to one embodiment of the present invention, a photoluminescence spectrum in a solution state (tetrahydrofuran (THF)) and a photoluminescence spectrum in a low-temperature state, The UV-vis absorption spectrum was measured using V-730 manufactured by JASCO, and the absorption spectrum was 200 nm to 750 nm. A ⁵ M ^- as a solvent was used as the HPLC grade THF, the amount of the compound 1 is 10. The photoluminescence spectrum in the solution state It was measured using LS-55 manufactured by Perkin Elmer, and the emission spectrum at an excitation wavelength of 300 nm was 400 nm to 7000 nm. HPLC grade THF was used as a solvent. The light emission spectrum in the low-temperature state was measured using LS-55 manufactured by Perkin Elmer, and the emission spectrum at the excitation wavelength of 390 nm was 300 nm to 750 nm. HPLC grade THF was used as solvent and measured under liquid nitrogen.

The physical properties of the compound 1 according to FIG. 3 are shown in Table 1 below.

UV edge
(nm) UV gap
(eV) Fluorescent PL Phosphorescent PL Singlet energy (eV) Triplet energy (eV) S1-T1
(Max) Max peak Max peak Max peak Max peak Compound 1 463 2.68 492 499 2.52 2.48 0.04

In Table 1, the emission peak wavelength in the liquid state is 492 nm and the emission peak wavelength in the low-temperature state is 499 nm.

Production Example 2. Preparation of Compound 2

(1) Preparation of intermediate 2-1

8.0 g (35.7 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine and 14.8 g (107.1 mmol) of potassium carbonate were dissolved in tetrahydrofuran was dissolved in a mixed solvent of 140 mL of distilled water and 70 mL, followed by the addition of _{Pd (PPh 3) 4 1.2 g} (1.07 mmol) was refluxed for 12 hours. After cooling to room temperature, the water layer was removed, and an anhydrous magnesium sulfate was added to the organic layer, followed by filtration. Concentrated and purified by column chromatography to obtain Intermediate 2-1 (7.4 g, yield 73%).

(2) Preparation of intermediate 2-2

7.4 g (25.96 mmol) of Intermediate 2-1, 2.1 g (12.98 mmol) of 1,4-phenylenediboronic acid and 7.2 g (51.9 mmol) of potassium carbonate were dissolved in a mixed solvent of 50 mL of tetrahydrofuran and 25 mL of distilled water, (PPh ₃₎ followed by the addition of ₄ 0.6 g (0.5 mmol) was refluxed for 12 hours. After cooling to room temperature, the water layer was removed, and an anhydrous magnesium sulfate was added to the organic layer, followed by filtration. Concentrated and purified by column chromatography to obtain intermediate 2-2 (6.0 g, yield 80%).

(3) Preparation of Compound 2

6.0 g (10.41 mmol) of Intermediate 2-2, 3.5 g (20.82 mmol) of 9H-carbazole and 13.6 g (41.64 mmol) of cesium carbonate were placed in Dimethylformamide (83 ml) and stirred under reflux. After the completion of the reaction, the reaction mixture was filtered through silica gel / celite, concentrated under reduced pressure, and separated into a column. The resulting solution was concentrated under reduced pressure, then crystallized with hexane and filtered to obtain Compound 2 (6.3 g, yield 70%).

MS [M + H] < ⁺ > = 871

Production Example 3. Preparation of Compound 3

(1) Preparation of intermediate 3-1

Except that 5.0 g (35.7 mmol) of (4-fluorophenyl) boronic acid was used instead of 5.0 g (35.7 mmol) of (2-fluorophenyl) boronic acid in the preparation of Intermediate 1-1 of (1) 1, 7.2 g (yield 71%) of Intermediate 3-1 was obtained.

(2) Preparation of intermediate 3-2

(2) Intermediate 1-2 in Preparation Example 1 was replaced by 7.2 g (25.25 mmol) of Intermediate 3-1 instead of 7.7 g (27.01 mmol) of Intermediate 1-1 and 2.24 g (13.5 mmol) of the above 1,4-phenylenediboronic acid ) And 1,4-phenylenediboronic acid (2.1 g, 12.63 mmol), 7.4 g (73% yield) of Intermediate 3-2 was obtained.

(3) Preparation of Compound 3

(6.3 g, 10.93 mmol) and Intermediate 3-2 7.4 (3.9 mmol) instead of 6.1 g (21.86 mmol) of 3,6-di-tert- g (12.84 mmol) of 3,6-di-tert-butyl-9H-carbazole and 7.2 g (25.68 mmol) of 3,6-di-tert-butyl-9H-carbazole was used in the same manner as in Example 1 to obtain 9.3 g (66%

MS [M + H] < ⁺ > = 1095

Production Example 4. Preparation of Compound 4

(1) Preparation of intermediate 4-1

2 - ([1,1'-biphenyl] -1,3,4-triazine was obtained in the same manner as in Preparation Example 1, except that 8.0 g (35.7 mmol) of 2,4-dichloro- -2-yl) -4,6-dichloro-1,3,5-triazine was used in place of 12.9 g (35.7 mmol) of Intermediate 4-1.

(2) Preparation of intermediate 4-2

8.9 g (24.64 mmol) of Intermediate 4-1 instead of 7.7 g (27.01 mmol) of Intermediate 1-1 and 2.24 g (13.5 mmol) of the above 1,4-phenylenediboronic acid were used in the preparation of Intermediate 1-2 of (2) ) And 1.4 g of phenylenediboronic acid (2.0 g, 12.32 mmol). 12.5 g (70% yield) of Intermediate 4-2 was obtained.

(3) Preparation of Compound 4

In the preparation of compound (1) (3) of Preparation Example 1, 6.3 g (10.93 mmol) of Intermediate 1-2 and 6.1 g (21.86 mmol) of 3,6-di-tert- g (17.16 mmol) of 9H-carbazole and 5.7 g (34.32 mmol) of 9H-carbazole were used in the same manner as in the preparation of Compound 1, and 11.6 g (yield 66%) of Compound 4 was obtained.

MS [M + H] < ⁺ > = 1023

Production Example 5. Preparation of Compound 5

(1) Preparation of intermediate 5-1

5.0 g (35.7 mmol) of (2-fluorophenyl) boronic acid and 8.0 g (35.7 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine in the preparation of Intermediate 1-1 of (1) 5.0 g (35.7 mmol) of (3-fluorophenyl) boronic acid and 12.9 g (2.8 mmol) of 2 - ([1,1'-biphenyl] -3-yl) -4,6-dichloro-1,3,5- (65% yield) of Intermediate 5-1 was obtained.

(2) Preparation of intermediate 5-2

8.4 g (23.26 mmol) of Intermediate 5-1 was used instead of 7.7 g (27.01 mmol) of Intermediate 1-1 and 2.24 g (13.5 mmol) of 1,4-phenylenediboronic acid in the preparation of Intermediate 1-2 of (2) ) And 1,4-phenylenediboronic acid (1.9 g, 11.63 mmol), 12.1 g (yield 68%) of Intermediate 5-2 was obtained.

(3) Preparation of Compound 5

(3) Compound 1 in Preparation Example 1 was used instead of 6.3 g (10.93 mmol) of Intermediate 1-2 and 6.1 g (21.86 mmol) of 3,6-di-tert-butyl-9H- g (16.6 mmol) of 3,6-dimethyl-9H-carbazole and 6.5 g (33.2 mmol) of 3,6-dimethyl-9H-carbazole. 11.1 g (yield 62%) of Compound 5 was obtained.

MS [M + H] < ⁺ > = 1079

Production Example 6. Preparation of Compound 6

(1) Preparation of intermediate 6-1

2 - ([1,1'-biphenyl] -1,3,4-triazine was obtained in the same manner as in Preparation Example 1, except that 8.0 g (35.7 mmol) of 2,4-dichloro- -4-yl) -4,6-dichloro-1,3,5-triazine was used instead of 12.9 g (35.7 mmol) of Intermediate 6-1.

(2) Preparation of intermediate 6-2

9.1 g (25.20 mmol) of Intermediate 6-1 instead of 7.7 g (27.01 mmol) of Intermediate 1-1 and 2.24 g (13.5 mmol) of the above 1,4-phenylenediboronic acid were used in the preparation of Intermediate 1-2 of (2) ) And 1,4-phenylenediboronic acid (1.9 g, 12.60 mmol), 12.4 g (yield 70%) of Intermediate 6-2 was obtained.

(3) Preparation of Compound 6

Intermediate 6-2 was obtained in the same manner as Intermediate 6-2 (12.9 mmol) instead of 6.3 g (10.93 mmol) of Intermediate 1-2 and 6.1 g (21.86 mmol) of 3,6-di-tert- g (17.03 mmol) and 9H-carbazole (5.7 g, 34.05 mmol). Compound 6 was obtained in an amount of 10.6 g (61%

MS [M + H] < ⁺ > = 1023

Example 1-1. Fabrication of organic light emitting device

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

On the prepared ITO transparent electrode, the following N1, N1 '- ([1,1'-biphenyl] -4,4'-diyl) bis (N1-phenyl-N4, N4- ) [DNTPD] was deposited by thermal vacuum deposition to a thickness of 600 Å to form a hole injection layer. ([1,1'-biphenyl] -4-yl) - [1,1'-biphenyl] -4,4'-diamine [BPBPA], N4, N4 ' And 9,9-dimethyl-10- (9-phenyl-9H-carbazol-3-yl) -9,10-dihydroacridine [PCZAC] 600 Å were successively vacuum deposited thereon to form a hole transport layer. Subsequently, 9 - (3 '- (4,6-diphenyl-1,3,5-triazin-2-yl) - [1,1'- biphenyl] -3-yl) -9H-carbazole [DCz] and Compound 1 were vacuum-deposited at a weight ratio of 20: 1 to form a light emitting layer.

Dibenzo [b, d] furan [DBFTrz] and the following 2- (4- (9,10- An electron transport layer was formed in a thickness of 350 angstroms sequentially on a glass substrate with di (naphthalen-2-yl) anthracen-2-yl) phenyl-1-phenyl-1H-benzo [d] imidazole [ZADN]. Lithium fluoride (LiF) and aluminum were sequentially deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer and a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 A / sec, the deposition rate of lithium fluoride at 0.3 A / sec for aluminum and 2 A / sec at aluminum was maintained, and the degree of vacuum during deposition was 1 x 10 < by keeping the ^-7 to 5 × 10 ^-8 torr, an organic light emitting device was produced.

Examples 1-2

An organic light emitting device was fabricated in the same manner as in Example 1-1, except that Compound 2 was used instead of Compound 1 in Example 1-1.

Example 1-3

An organic light emitting device was fabricated in the same manner as in Example 1-1, except that Compound 3 was used instead of Compound 1 in Example 1-1.

Examples 1-4

An organic light emitting device was fabricated in the same manner as in Example 1-1, except that Compound 4 was used instead of Compound 1 in Example 1-1.

Examples 1-5

An organic light emitting device was fabricated in the same manner as in Example 1-1, except that Compound 5 was used instead of Compound 1 in Example 1-1.

Examples 1-6

An organic light emitting device was fabricated in the same manner as in Example 1-1, except that Compound 6 was used instead of Compound 1 in Example 1-1.

Comparative Example 1-1

An organic luminescent device was fabricated in the same manner as in Example 1-1 except that D1 was used in place of Compound 1 in Example 1-1.

Comparative Example 1-2

An organic light emitting device was fabricated in the same manner as in Example 1-1 except that the compound D2 was used in place of the compound 1 in Example 1-1.

Comparative Example 1-3

An organic light emitting device was fabricated in the same manner as in Example 1-1, except that D3 was used instead of Compound 1 in Example 1-1.

Device evaluation

The organic light-emitting devices fabricated in Examples 1-1 to 1-6 and Comparative Examples 1-1 to 1-3 were fabricated by using a PR-655 IVL instrument manufactured by Photo Research Co., Ltd. under the current-voltage-luminance (luminance) IVL), color coordinates (CIE), quantum efficiency (QE), luminous efficiency (LE) and current efficiency (J) were measured. The results are shown in Tables 2 and 3 below.

Voltage
(V) Current density
(A / Cm ² ) Luminance
(cd / m ² ) Color coordinates (CIE) x y Example 1-1 5.8 2.4 1000.7 0.25 0.51 Examples 1-2 5.7 2.2 997.8 0.24 0.54 Example 1-3 6.0 2.2 999.4 0.25 0.52 Examples 1-4 5.5 2.0 1001.6 0.26 0.51 Examples 1-5 5.8 1.9 1000.2 0.25 0.50 Examples 1-6 6.0 2.1 998.8 0.27 0.49 Comparative Example 1-1 7.8 1.4 997.5 0.22 0.54 Comparative Example 1-2 8.1 1.4 998.9 0.23 0.52 Comparative Example 1-3 8.0 1.6 997.1 0.24 0.51

Quantum efficiency (%) Luminescent efficiency (lm / W) Current efficiency (Cd / A) 1000cd max. 1000cd max. 1000cd max. Example 1-1 19.2 23.7 25.4 29.1 49.4 52.8 Examples 1-2 19.6 24.9 25 32.5 49.1 53.3 Example 1-3 20.5 26.4 26.5 33.7 51.9 55.4 Examples 1-4 19.9 24.3 28.3 35 51.7 53 Examples 1-5 19.7 23.5 24.8 29.4 50.1 53.7 Examples 1-6 20.1 26.7 25.7 30.8 48.7 54.4 Comparative Example 1-1 15.7 19.1 21.2 23.3 40.1 43.7 Comparative Example 1-2 16.6 18.6 20.4 24.4 43 47.8 Comparative Example 1-3 16.0 18.0 19.1 21.3 41.0 42.4

As can be seen from the results of Examples 1-1 to 1-6 and Comparative Examples 1-1 to 1-3 of Tables 2 and 3, the retarded fluorescent material according to one embodiment of the present invention includes triazine, The organic luminescent device using the organic luminescent device as a dopant of the organic luminescent device has a driving voltage lower than that of the organic luminescent devices of Comparative Examples 1-1 to 1-3 in which D1 to D3, which are pyridine or pyrimidine-containing compounds, High density and high brightness, and is excellent in quantum efficiency, luminous efficiency and current efficiency.

10: Organic light emitting device
20: substrate
30: first electrode
40: light emitting layer
50: second electrode

Claims (13)

A retardation fluorescent material comprising a compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
R1 and R2 are the same or different and are each independently an aryl group,
R3 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R11 to R13 and R111 to R113 are the same or different and are each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
n1, m1 and m11 are each 0 or 1,
r3, r11 to r13 and r111 to r113 are each an integer of 1 to 4,
When r3, r11 to r13 and r111 to r113 are respectively 2 or more, the structures in parentheses of 2 or more are the same or different from each other. The retardation fluorescent material according to claim 1, wherein the triplet energy level of the compound represented by Formula 1 is 2.0 eV or more. The retardation fluorescent material according to claim 1, wherein the difference between the singlet energy level and the triplet energy level of the compound represented by the formula (1) is 0.3 eV or less. The compound according to claim 1, wherein R11, R12, R111 and R112 are the same or different from each other, and each independently hydrogen; Or an alkyl group. The delayed fluorescence material according to claim 1, wherein the formula (1) is selected from the following compounds:

A first electrode;
A second electrode facing the first electrode; And
Wherein at least one of the organic material layers comprises the retardation fluorescent material of any one of claims 1 to 5, wherein the organic light emitting device comprises at least one organic material layer provided between the first electrode and the second electrode, . The organic light emitting device according to claim 6, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the retardation fluorescent material. 7. The organic light emitting device according to claim 6, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the retardation fluorescent material as a dopant of the light emitting layer. 7. The organic electroluminescent device according to claim 6, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes at least one selected from the following Chemical Formulas A to F as a host of the light emitting layer:
(A)

In the above formula (A)
Y1 is NR ', S or O,
q1 is an integer of 0 to 3,
R 'is an alkyl group; Or an aryl group,
[Chemical Formula B]

In the above formula (B)
Y2 is O or S,
L1 is a biphenyllylene group; A fluorenylene group substituted or unsubstituted with an alkyl group or an aryl group; Or a spirobifluorenylene group,
A 1 is an alkyl group, a silyl group substituted with an alkyl group, or a carbazolyl group substituted or unsubstituted with an aryl group,
≪ RTI ID = 0.0 &

In the above formula (C)
Q1 to Q8 are the same or different from each other, and each independently hydrogen; An aryl group substituted or unsubstituted with a heteroaryl group; Or a heteroaryl group, or adjacent groups may combine with each other to form a heterocyclic ring which is substituted or unsubstituted with an aryl group or a heteroaryl group,
[Chemical Formula D]

(E)

[Chemical Formula F]

In Formula (F) above,
Y3 is a direct bond; Or O,
Q9 and Q10 are the same or different from each other, and each independently hydrogen; Or a heteroaryl group substituted with an aryl group,
q9 and q10 are each an integer of 1 to 4,
q11 is 1 or 2,
When q9 and q10 are each 2 or more, the structures in parentheses of 2 or more are the same or different from each other. [Claim 11] The organic electroluminescent device according to claim 9, wherein L1 is any one selected from the following structures:

10. The organic electroluminescent device according to claim 9, wherein A1 is represented by the following structure:

In the above structure,
A2 and A3 are the same or different from each other, and each independently hydrogen; An alkyl group; A silyl group substituted with an alkyl group; Or an aryl group,
o and p are each an integer of 1 to 4,
When o and p are each 2 or more, the structures in parentheses of 2 or more are the same or different from each other. 7. The organic light emitting device according to claim 6, wherein the organic layer includes a light emitting layer, and the light emitting layer further comprises a fluorescent dopant. The organic light-emitting device according to claim 12, wherein the fluorescent dopant comprises at least one selected from the following formulas (G) and (H):
[Formula G]

[Formula H] <

In the above formulas G and H,
Ar1 to Ar4 and G1 to G4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

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