KR102144174B1 - Delayed fluorescence material and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a delayed fluorescent material made of the compound of Formula 1 and an organic light emitting device including the same.

Description

Delayed fluorescent material and organic light-emitting device comprising the same TECHNICAL FIELD [0002] DELAYED FLUORESCENCE MATERIAL AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

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

The present specification relates to a delayed 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 light-emitting materials, and for this purpose, studies on phosphorescent and delayed fluorescent materials are being actively conducted. However, in the case of the phosphorescent material, although high efficiency can be achieved, there is a problem in that the cost of the metal complex required to implement phosphorescence is high and the lifespan is short.

In the case of delayed fluorescent materials, the concept of thermally activated delayed fluorescence (TADF) was recently introduced to introduce a highly efficient green fluorescent material that is a fluorescent material and has high external quantum efficiency. The concept of thermally activated delayed fluorescence (TADF) represents a phenomenon leading to fluorescence emission by causing the reverse energy transfer from the excitation triplet state to the excitation singlet state by thermal activation, and since light emission occurs through the triplet, the lifespan is generally reduced. It is called delayed fluorescence in that long light emission occurs. Since the delayed fluorescent material can use both fluorescence emission and phosphorescence emission, the problem of external quantum efficiency of the conventional fluorescent material can be solved, and the price problem of the phosphorescent material can be solved in that it does not need to contain a metal complex.

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

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

According to an exemplary embodiment of the present specification, a delayed fluorescent material composed of a compound represented by the following Formula 1 is provided.

[Formula 1]

In Formula 1,

R1 and R2 are the same as or different from each other, and 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 as or different from each other, and 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 each 2 or more, the structures in the two or more parentheses are the same or different from each other.

In addition, according to an exemplary embodiment of the present specification, the first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the delayed fluorescent material.

The organic light-emitting device using the delayed fluorescent material made of the compound represented by Formula 1 according to an exemplary embodiment of the present specification can improve efficiency, low driving voltage, and/or improve lifespan characteristics.

1 shows an organic light emitting device according to an exemplary embodiment of the present specification.
2 is a diagram showing an MS graph of Compound 1 according to an exemplary embodiment of the present specification.
FIG. 3 is a UV-vis absorption spectrum of Compound 1 according to an exemplary embodiment of the present specification, a photoluminescence spectrum in a solution state (toluene or tetrahydrofuran (THF)), and a photoluminescence spectrum in a low temperature (Low-Temperature) state. to be.

According to an exemplary embodiment of the present specification, there is provided a delayed fluorescent material made of the compound represented by Formula 1 above.

The compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification includes a triazine group acting as an electron acceptor, and electron injection is easy, and an organic light emitting device using this as a delayed fluorescent material has high efficiency and long lifespan.

In addition, the compound represented by Formula 1 includes a phenylene group as a linker between each triazine group, and a phenylene group between the triazine group and carbazole group is introduced as a linker, thereby enhancing battery injection characteristics and using it as a light emitting layer. In the organic light emitting device, the efficiency of the device may 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 emission spectrum is the same as that of fluorescence, but the decay time is long.Although the attenuation time is long, the peak position of the emission spectrum is as much as the difference between the phosphorescence spectrum and the S ₁ -T ₁ energy. It differs from phosphorescence in that it is different.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 includes a phenylene group as a linker between each triazine group, and by introducing a phenylene group as a linker between the triazine group and carbazole group, The energy difference between the singlet state and the triplet state can be properly adjusted. Through this, thermally activated delayed fluorescence (TADF) can be represented.

According to an exemplary embodiment of the present specification, 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, and even 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 life, and excellent luminous efficiency may be implemented.

According to one embodiment of the present specification, 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, and 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-triplet energy level. When the difference between the singlet energy level and the triplet energy level satisfies the above range, the intramolecular orbital overlap is effectively blocked so that the singlet and the triplet do not overlap, very low It may have the difference value. Through this, an inverse interphase transition from a triplet excited state to a singlet excited state through thermal activity is possible even at room temperature, thereby exhibiting delayed fluorescence.

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

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

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

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

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; 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 alkyl thioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; 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 substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituent. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to 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 of the imide group is not particularly limited, but it 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 nitrogen of the amide group may be substituted with hydrogen, a straight-chain, branched or cyclic alkyl group having 1 to 30 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 number of carbon atoms 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 a C1-C25 linear, branched or cyclic alkyl group 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 a straight chain or a branched chain, and carbon number 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, but are not limited thereto.

In the present specification, the cycloalkyl group may be monocyclic or polycyclic, and is not particularly limited, but is preferably 3 to 30 carbon atoms, specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3- Dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl And the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. Although the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but It is not limited.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group are methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine Group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, and the like, but is not limited thereto.

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

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

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

In the present specification, the alkyl group in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is the same as the example of the alkyl group described above. Specifically, the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, and an octyl thioxy group. And the like, but are not limited thereto.

In the present specification, the alkenyl group may be a linear or branched chain, 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, steelbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted C 1 to C 30 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.

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. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, 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 has 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, phenalenyl group, perylenyl group, chrysenyl group, fluorenyl group, fluoranthenyl group, etc. , But is not limited thereto.

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

,

,

,

,

및

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

,

,

,

,

And

Etc. However, it is not limited thereto.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. Can. For example, two substituents substituted in the ortho position on the benzene ring 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 groups in the aryloxy group, arylthioxy group, arylsulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group are the same as those of the aryl group described above. Specifically, the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-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 a phenylthioxy group, 2- There are a methylphenyl thioxy group, a 4-tert-butylphenyl thioxy group, and the like, and the aryl sulfoxy group includes a benzene sulfoxy group and a p-toluene sulfoxy group, but 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 containing 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, the heteroaryl group includes one or more non-carbon atoms, heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. 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 thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolyl group, quinazolyl group, quinoxalyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, p Nanthrolinyl group (phenanthroline), isoxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are 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 containing two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group 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, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as those of the aforementioned heteroaryl group.

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

[Formula 1-1]

In Formula 1-1,

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

R11, R12, R111 and R112 are the same as or different from each other, and 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 each 2 or more, the structures in the two or more parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently a phenyl group; Or a biphenyl group.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently a phenyl group; 2-biphenyl group; 3-biphenyl group; Or 4-biphenyl group.

According to an exemplary embodiment of the present specification, in Formula 1, R11, R12, R111, and R112 are the same as or different from each other, and each independently hydrogen; Or an alkyl group.

According to an exemplary embodiment of the present specification, in Formula 1, R11, R12, R111, and R112 are the same as or different from each other, and each independently hydrogen; Methyl group; Or t-butyl group.

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

According to an exemplary embodiment of the present specification, an organic light emitting device including a delayed fluorescent material made of the compound represented by Formula 1 is provided.

According to an exemplary embodiment of the present specification, the first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the above-described delayed fluorescent material.

The organic material layer of the organic light emitting device of the present specification 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 injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like 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 specification 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 device according to an exemplary embodiment of the present specification, and may further include another organic material layer.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the above-described delayed fluorescent material.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the above-described delayed fluorescent material as a dopant of the emission layer.

According to an exemplary embodiment of the present specification, the light emitting material of the light emitting layer is a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, wherein the light emitting layer is the aforementioned delayed fluorescent material. As a dopant of the light emitting layer, wherein at least one of the excitation singlet energy and the excitation triplet energy has a higher value than the light emitting material of the above-described delayed fluorescent material, has a hole transporting ability, an electron transporting ability, and a long wavelength of light emission An organic compound having a high glass transition temperature and a high glass transition temperature may be included as a host.

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

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes any one or more selected from Formulas A to F below as a host of the emission layer.

[Formula A]

In Formula A,

Y1 is NR', S or O,

q1 is an integer from 0 to 3,

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

[Formula B]

In the formula B,

Y2 is O or S,

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

A1 is an alkyl group, a silyl group substituted with an alkyl group, or a carbazolyl group unsubstituted or substituted with an aryl group,

[Chemical Formula C]

In Formula C,

Q1 to Q8 are the same as or different from each other, and each independently hydrogen; An aryl group unsubstituted or substituted with a heteroaryl group; Or a heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted heterocycle with an aryl group or heteroaryl group,

[Formula D]

[Formula E]

[Formula F]

In the formula F,

Y3 is a direct bond; Or O,

Q9 and Q10 are the same as 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 the two or more parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes a dopant and a host in a weight ratio of 1:99 to 10:90.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes a dopant including the above-described delayed fluorescent material, and a host including at least one selected from Formulas A to F. Included in a weight ratio of 10:90.

According to an exemplary embodiment of the present specification, in Formula B, L1 is any one selected from the following structures.

According to an exemplary embodiment of the present specification, in Formula B, A1 is represented by the following structure.

In the above structure,

A2 and A3 are the same as or different from each other, and each independently hydrogen; 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 the two or more parentheses are the same or different from each other.

According to another exemplary embodiment of the present specification, A2 and A3 are the same as or different from each other, and each independently hydrogen; Methyl group; t-butyl group; Trimethylsilyl group; Phenyl group; Or a biphenyl group.

According to an exemplary embodiment of the present specification, in Chemical Formula C, Q1 to Q8 are the same as or different from each other, and each independently hydrogen; A phenyl group unsubstituted or substituted with a carbazolyl group or a dibenzofuran group; Biphenyl group; Terphenyl group; Or a carbazolyl group.

According to an exemplary embodiment of the present specification, in Formula C, adjacent groups of Q1 to Q8 combine with each other to form a benzofuran ring unsubstituted or substituted with an aryl group or a heteroaryl group.

According to an exemplary embodiment of the present specification, in Formula C, adjacent groups of Q1 to Q8 are bonded to each other to form a benzofuran ring unsubstituted or substituted with a biphenyl group, terphenyl group, or carbazolyl group.

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

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

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

According to an exemplary embodiment of the present specification, in Formula F, q11 is 1.

According to an exemplary embodiment of the present specification, in Formula F, q11 is 2.

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

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer further includes a fluorescent dopant.

According to an exemplary embodiment of the present specification, the emission layer includes the above-described delayed fluorescent material as a dopant, includes any one or more of the aforementioned Formulas A to F as a host, and further includes an additional fluorescent dopant.

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

According to an exemplary embodiment of the present specification, the fluorescent dopant includes any one or more selected from the following Chemical 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 as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; 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 alkyl thioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; 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 light-emitting device of the present specification includes the delayed fluorescent material of the present specification as a dopant of the emission layer, that is, a delayed fluorescent material composed of the compound represented by Chemical Formula 1, and as a host of the emission layer, among the aforementioned Chemical Formulas A to F Except for including one or more selected, it can be made by materials and methods known in the art.

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 can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) such as sputtering or e-beam evaporation, a metal or conductive metal oxide or alloy thereof is deposited on the substrate. It can be manufactured by forming a first electrode, forming an organic material layer including a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer thereon, and then depositing a material that can be used as a second electrode thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. In addition, the heterocyclic compound represented by Formula 1 may be formed as 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 application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

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

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

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

It is preferable that the cathode material is 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; There are multilayered materials such as LiF/Al, LiO ₂ /Al, or Mg/Ag, but are not limited thereto.

The hole injection layer is a layer that injects holes from an electrode as a hole injection material, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material. , A compound that prevents the movement of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferable. 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 hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

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

The electron transport material of the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. The electron transport material is a material that can receive electrons from the cathode and transfer them to the emission 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 transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

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

Hereinafter, examples will be described in detail in order to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.

Preparation Example 1. Preparation of compound 1

(1) Preparation of Intermediate 1-1

(2-fluorophenyl)boronic acid 5.0 g (35.7 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine 8.0 g (35.7 mmol), potassium carbonate 14.8 g (107.1 mmol) in tetrahydrofuran It was dissolved in a mixed solvent of 140 mL and 70 mL of distilled water, and 1.2 g (1.07 mmol) of Pd(PPh ₃ ) ₄ was added, followed by refluxing for 12 hours. After cooling to room temperature, the water layer was removed, and anhydrous magnesium sulfate was added to the organic layer, followed by filtration. After concentration, it was purified by column chromatography to obtain Intermediate 1-1 (7.7 g, yield 76%).

(2) Preparation of Intermediate 1-2

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

(3) Preparation of compound 1

6.3 g (10.93 mmol) of the intermediate 1-2, 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) and stirred under reflux. I did. When the reaction was completed, the reaction solution was filtered through silica gel/celite, concentrated under reduced pressure, and separated by a column. The resulting evolving solution was concentrated under reduced pressure, crystallized with hexane, and filtered to obtain compound 1 (8.1 g, yield 68%).

MS[M+H] ⁺ = 1095

2 is a diagram showing an MS graph of Compound 1.

3 is a UV-vis absorption spectrum of Compound 1 according to an exemplary embodiment of the present specification, 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 JASCO's V-730, 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 solution is It was measured using a Perkin Elmer's LS-55, and the emission spectrum at an excitation wavelength of 300 nm is 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 the LS-55 of Perkin Elmer, and the emission spectrum at the excitation wavelength of 390 nm is 300 nm to 750 nm. HPLC grade THF was used as a solvent, and it was measured under liquid nitrogen.

The physical properties of 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.

Preparation Example 2. Preparation of Compound 2

(1) Preparation of Intermediate 2-1

(3-fluorophenyl)boronic acid 5.0 g (35.7 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine 8.0 g (35.7 mmol), potassium carbonate 14.8 g (107.1 mmol) in tetrahydrofuran It was dissolved in a mixed solvent of 140 mL and 70 mL of distilled water, and 1.2 g (1.07 mmol) of Pd(PPh ₃ ) ₄ was added, followed by refluxing for 12 hours. After cooling to room temperature, the water layer was removed, and anhydrous magnesium sulfate was added to the organic layer, followed by filtration. After concentration, it was 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 the 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, and Pd (PPh ₃ ) ₄ 0.6 g (0.5 mmol) was added and then refluxed for 12 hours. After cooling to room temperature, the water layer was removed, and anhydrous magnesium sulfate was added to the organic layer, followed by filtration. After concentration, the mixture was purified by column chromatography to obtain Intermediate 2-2 (6.0 g, yield 80%).

(3) Preparation of compound 2

The intermediate 2-2 6.0 g (10.41 mmol), 9H-carbazole 3.5 g (20.82 mmol) and Cesium carbonate 13.6 g (41.64 mmol) were added to Dimethylformamide (83 ml) and stirred under reflux. When the reaction was completed, the reaction solution was filtered through silica gel/celite, concentrated under reduced pressure, and separated by a column. The resulting developing solution was concentrated under reduced pressure, crystallized with hexane, and filtered to obtain compound 2 (6.3 g, yield 70%).

MS[M+H] ⁺ = 871

Preparation Example 3. Preparation of compound 3

(1) Preparation of Intermediate 3-1

In the preparation of (1) Intermediate 1-1 of Preparation Example 1 above, except for using 5.0 g (35.7 mmol) of (4-fluorophenyl)boronic acid instead of 5.0 g (35.7 mmol) of (2-fluorophenyl)boronic acid, Intermediate 1- Prepared in the same manner as in Preparation Example 1 to obtain 7.2 g (71% yield) of Intermediate 3-1.

(2) Preparation of Intermediate 3-2

In the preparation of (2) Intermediate 1-2 of Preparation Example 1, 7.7g (27.01 mmol) of Intermediate 1-1 and 7.2 g (25.25 mmol) of Intermediate 3-1 instead of 2.24g (13.5 mmol) of 1,4-phenylenediboronic acid ) And 1,4-phenylenediboronic acid 2.1 g (12.63 mmol) was prepared in the same manner to obtain 7.4 g (73% yield) of Intermediate 3-2.

(3) Preparation of compound 3

In the preparation of (3) compound 1 of Preparation Example 1, 6.3 g (10.93 mmol) of the intermediate 1-2 and 6.1 g (21.86 mmol) of 3,6-di-tert-butyl-9H-carbazole were replaced with 7.4 of the intermediate 3-2. g (12.84 mmol) and 7.2 g (25.68 mmol) of 3,6-di-tert-butyl-9H-carbazole were prepared in the same manner to obtain 9.3 g (66% yield) of compound 3.

MS[M+H] ⁺ = 1095

Preparation Example 4. Preparation of compound 4

(1) Preparation of intermediate 4-1

In the preparation of (1) intermediate 1-1 of Preparation Example 1, 2,4-dichloro-6-phenyl-1,3,5-triazine 8.0 g (35.7 mmol) instead of 2-([1,1'-biphenyl] -2-yl)-4,6-dichloro-1,3,5-triazine 12.9 g (35.7 mmol) was prepared in the same manner, except that 8.9 g (yield 69%) of intermediate 4-1 was obtained.

(2) Preparation of intermediate 4-2

In the preparation of (2) Intermediate 1-2 of Preparation Example 1, 7.7g (27.01 mmol) of Intermediate 1-1 and 8.9 g (24.64 mmol) of Intermediate 4-1 instead of 2.24g (13.5 mmol) of 1,4-phenylenediboronic acid ) And 2.0 g (12.32 mmol) of 1,4-phenylenediboronic acid were prepared in the same manner to obtain 12.5 g (70% yield) of Intermediate 4-2.

(3) Preparation of compound 4

In the preparation of (3) compound 1 of Preparation Example 1, 6.3 g (10.93 mmol) of Intermediate 1-2 and 6.1g (21.86 mmol) of 3,6-di-tert-butyl-9H-carbazole were replaced with Intermediate 4-2 12.5 Except for using g (17.16 mmol) and 5.7 g (34.32 mmol) of 9H-carbazole, the reaction was carried out in the same manner as in Preparation Example 1 above and purified to obtain 11.6 g (66% yield) of compound 4.

MS[M+H] ⁺ = 1023

Preparation Example 5. Preparation of compound 5

(1) Preparation of Intermediate 5-1

In the preparation of (1) Intermediate 1-1 of Preparation Example 1, 5.0 g (35.7 mmol) of (2-fluorophenyl)boronic acid and 8.0 g (35.7 of 2,4-dichloro-6-phenyl-1,3,5-triazine) mmol) instead of (3-fluorophenyl)boronic acid 5.0 g (35.7 mmol) and 2-([1,1'-biphenyl]-3-yl)-4,6-dichloro-1,3,5-triazine 12.9 g ( 35.7mmol) was prepared in the same manner, except that 8.4 g (yield 65%) of intermediate 5-1 was obtained.

(2) Preparation of intermediate 5-2

In the preparation of (2) Intermediate 1-2 of Preparation Example 1, 7.7g (27.01 mmol) of Intermediate 1-1 and 8.4 g (23.26 mmol) of Intermediate 5-1 instead of 2.24g (13.5 mmol) of 1,4-phenylenediboronic acid ) And 1.9 g (11.63 mmol) of 1,4-phenylenediboronic acid were prepared in the same manner to obtain 12.1 g (68% yield) of Intermediate 5-2.

(3) Preparation of compound 5

In the preparation of (3) compound 1 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-butyl-9H-carbazole were replaced with Intermediate 5-2 12.1 g (16.6 mmol) and 6.5 g (33.2 mmol) of 3,6-dimethyl-9H-carbazole were prepared in the same manner to obtain 11.1 g (62% yield) of compound 5.

MS[M+H] ⁺ = 1079

Preparation Example 6. Preparation of compound 6

(1) Preparation of Intermediate 6-1

In the preparation of (1) intermediate 1-1 of Preparation Example 1, 2,4-dichloro-6-phenyl-1,3,5-triazine 8.0 g (35.7 mmol) instead of 2-([1,1'-biphenyl] -4-yl)-4,6-dichloro-1,3,5-triazine 12.9 g (35.7 mmol) was prepared by the same method, except that 9.1 g (71% yield) of Intermediate 6-1 was obtained.

(2) Preparation of intermediate 6-2

In the preparation of (2) Intermediate 1-2 of Preparation Example 1, 7.7g (27.01 mmol) of Intermediate 1-1 and 9.1 g (25.20 mmol) of Intermediate 6-1 instead of 2.24g (13.5 mmol) of 1,4-phenylenediboronic acid ) And 1.9 g (12.60 mmol) of 1,4-phenylenediboronic acid were prepared in the same manner to obtain 12.4 g (70% yield) of Intermediate 6-2.

(3) Preparation of compound 6

In the preparation of (3) compound 1 of Preparation Example 1, 6.3 g (10.93 mmol) of Intermediate 1-2 and 6.1g (21.86 mmol) of 3,6-di-tert-butyl-9H-carbazole were replaced with Intermediate 6-2 12.4 g (17.03 mmol) and 9H-carbazole 5.7 g (34.05 mmol) were prepared in the same manner to obtain 10.6 g (61% yield) of compound 6.

MS[M+H] ⁺ = 1023

Example 1-1. Fabrication of organic light emitting device

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the prepared ITO transparent electrode, the following N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine) )[DNTPD] was thermally vacuum deposited to a thickness of 600Å to form a hole injection layer. On the hole injection layer, the following N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine[BPBPA] 50Å and the following 9,9-dimethyl-10-(9-phenyl-9H-carbazol-3-yl)-9,10-dihydroacridine[PCZAC] 600Å were sequentially vacuum-deposited to form a hole transport layer. Then, the following 9-(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl) with a film thickness of 200Å on the hole transport layer -9H-carbazole[DCz] and Compound 1 were vacuum-deposited at a weight ratio of 20:1 to form a light emitting layer.

The following 2,8-bis(4,6-diphenyl-1,3,5-triazin-2-yl)dibenzo[b,d]furan[DBFTrz] and the following 2-(4-(9,10-) on the emission layer The electron transport layer was sequentially formed with di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole[ZADN] to a thickness of 350Å. Lithium fluoride (LiF) at a thickness of 10Å and aluminum at a thickness of 1,000Å were sequentially deposited on the electron transport layer to form an electron injection layer and a cathode.

In the above process, the deposition rate of organic materials was maintained at 0.4 to 0.9 Å/sec, lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å/sec, and for aluminum 2 Å/sec, the vacuum degree during deposition was 1 × 10 Maintaining ^-7 to 5 × 10 ^-8 torr, an organic light emitting device was manufactured.

Example 1-2

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

Example 1-4

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

Example 1-5

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

Example 1-6

An organic light-emitting device was manufactured 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 light-emitting device was manufactured in the same manner as in Example 1-1, except that D1 was used instead of Compound 1 in Example 1-1.

Comparative Example 1-2

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that D2 was used instead of Compound 1 in Example 1-1.

Comparative Example 1-3

An organic light-emitting device was manufactured 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 used with a PR-655 IVL meter manufactured by Photo Research, and current-voltage-luminance: IVL), color coordinate (CIE), quantum efficiency (QE), luminous efficiency (LE), and current efficiency (J) characteristics were measured, and the results are shown in Tables 2 and 3 below.

Voltage
(V) Current density
(A/Cm ² ) Luminance
(cd/m ² ) Color Coordinate (CIE) x y Example 1-1 5.8 2.4 1000.7 0.25 0.51 Example 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 Example 1-4 5.5 2.0 1001.6 0.26 0.51 Example 1-5 5.8 1.9 1000.2 0.25 0.50 Example 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 (%) Luminous 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 Example 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 Example 1-4 19.9 24.3 28.3 35 51.7 53 Example 1-5 19.7 23.5 24.8 29.4 50.1 53.7 Example 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 in Tables 2 and 3, the delayed fluorescent material according to an exemplary embodiment of the present specification includes triazine, The organic light-emitting device using this as a dopant of the organic light-emitting device has a lower driving voltage than the organic light-emitting device of Comparative Examples 1-1 to 1-3 in which the compounds D1 to D3, which are compounds containing pyridine or pyrimidine, are applied to the organic light-emitting device, and the current It has the advantage of high density, high luminance, and excellent 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)

Delayed fluorescent material consisting of a compound represented by the following formula (1):
[Formula 1]

In Formula 1,
R1 and R2 are the same as or different from each other, and each independently an aryl group,
R11, R12, R111 and R112 are the same as or different from each other, and 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 each 2 or more, the structures in the two or more parentheses are the same or different from each other The delayed fluorescent material according to claim 1, wherein the triplet energy level of the compound represented by Chemical Formula 1 is 2.0 eV or more. The delayed fluorescent material according to claim 1, wherein a difference between a singlet energy level and a triplet energy level of the compound represented by Formula 1 is 0.3 eV or less. The method according to claim 1, wherein R11, R12, R111 and R112 are the same as or different from each other, and each independently hydrogen; Or a delayed fluorescent material that is an alkyl group. The delayed fluorescent material of claim 1, wherein Formula 1 is selected from the following compounds:

A first electrode;
A second electrode provided opposite to the first electrode; And
An organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the delayed fluorescent material of any one of claims 1 to 5 . The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes the delayed fluorescent material. The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes the delayed fluorescent material as a dopant of the emission layer. The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes at least one selected from Formulas A to F as a host of the emission layer:
[Formula A]

In Formula A,
Y1 is NR', S or O,
q1 is an integer from 0 to 3,
R'is an alkyl group; Or an aryl group,
[Formula B]

In the formula B,
Y2 is O or S,
L1 is a biphenylylene group; A fluorenylene group unsubstituted or substituted with an alkyl group or an aryl group; Or a spirobifluorenylene group,
A1 is an alkyl group, a silyl group substituted with an alkyl group, or a carbazolyl group unsubstituted or substituted with an aryl group,
[Chemical Formula C]

In Formula C,
Q1 to Q8 are the same as or different from each other, and each independently hydrogen; An aryl group unsubstituted or substituted with a heteroaryl group; Or a heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted heterocycle with an aryl group or heteroaryl group,
[Formula D]

[Formula E]

[Formula F]

In the formula F,
Y3 is a direct bond; Or O,
Q9 and Q10 are the same as 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 the two or more parentheses are the same or different from each other. The organic light-emitting device of claim 9, wherein L1 is any one selected from the following structures:

The organic light-emitting device of claim 9, wherein A1 is represented by the following structure:

In the above structure,
A2 and A3 are the same as or different from each other, and each independently hydrogen; Alkyl groups; 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 the two or more parentheses are the same or different from each other. The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer further includes a fluorescent dopant. The organic light-emitting device of claim 12, wherein the fluorescent dopant comprises any one or more 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 as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; 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 alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; 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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