KR102342444B1 - Compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Compound and organic light emitting device including same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-00008585 filed with the Korean Intellectual Property Office on January 23, 2019, the entire contents of which are incorporated herein by reference.

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

The development of new materials for the organic light emitting device as described above is continuously required. Among them, in the case of a blue organic light emitting diode, high color purity and long lifespan characteristics are essential, but due to instability due to high energy of a blue material, there is a lack of technology for simultaneously implementing them. Recently, a thermally activated delayed fluorescent material having a core structure containing boron has been newly developed and has attracted attention for its high efficiency and color purity. Accordingly, there is a demand for the development of a blue organic light emitting body that simultaneously realizes high color purity and long life characteristics.

US Patent Application Publication No. 2004-0251816

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

The present invention provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

A is B or P,

Y1 and Y2 are the same as or different from each other and are each independently NR, O, or S;

L is a direct bond, a substituted or unsubstituted divalent tetracene group, a substituted or unsubstituted divalent pyrene group, a substituted or unsubstituted divalent benzoanthracene group, or a substituted or unsubstituted divalent perylene group,

X is hydrogen, a phenyl group, a tetracenyl group, a pyrenyl group, a benzoanthracenyl group, a perylenyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroaryl group, or represented by the formula (2),

When L is a direct bond, X is a tetracenyl group, a pyrenyl group, a benzoanthracenyl group, or a perylenyl group,

[Formula 2]

In Formula 2,

은 화학식 1의 L과 결합하는 위치를 의미하며,

means a position bonded to L of Formula 1,

A' is B or P;

Y1' and Y2' are the same as or different from each other, each independently represent NR', O, or S, R, R', R1 to R3 and R1' to R3' are the same as or different from each other, and each independently hydrogen, A nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted A cyclic aryl group, or a substituted or unsubstituted heteroaryl group,

may combine with adjacent groups to form a substituted or unsubstituted ring,

a, a' b and b' are each an integer from 0 to 4,

c and c' are each an integer from 0 to 2,

When a, a', b and b' are each 2 or more, the substituents in the parentheses are the same as or different from each other,

When c and c' are each 2, the substituents in parentheses are the same as or different from each other.

In addition, the present invention is a first electrode; a second electrode provided to face 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 compound.

The compound according to an exemplary embodiment of the present specification may be used as a material of an organic material layer of an organic light emitting device, and by using the compound, high color purity and/or lifespan characteristics may be improved in the organic light emitting device. Due to the fixed core structure including boron, high color purity can be realized, and a polycyclic ring with low triplet energy is connected to the boron emitter by a single bond to prevent reverse intersystem transition. Therefore, it is possible to implement long life characteristics and high color purity. In addition, due to the fixed core structure, there is little Stoke's shift, which is the difference between absorption and emission wavelength, so it is easy to select a host, and it helps to improve lifespan by using a host with less triplet energy compared to other blue light emitting materials can be

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

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

The present specification provides a compound represented by Formula 1 above.

The boron emitter having a narrow full width at half maximum has advantages of high efficiency and high purity, but has high triplet energy and slow inverse intersystem transition speed, so it has limitations in application to actual devices.

However, the compound of Formula 1 of the present invention lowers the triplet energy of the entire compound by connecting a polycyclic ring with low triplet energy to the boron emitter by a single bond, and has high planarity and a rigid structure of the core structure including boron. Due to this, it has higher EQE and higher color purity than conventional phosphors. In addition, it exhibits extended lifespan characteristics due to a stable compound structure.

Both HOMO and LUMO, which determine luminescence energy, are formed in polycyclic rings including boron, so it is possible to realize high EQE characteristics due to small Stokes change, narrow radius, high color purity, and high planarity of boron thermally activated delayed fluorescent material. do.

In addition, by linking a polycyclic ring with a low triplet energy to the boron core by a single bond, it is possible to extend the lifespan by preventing reverse intersystem transition that adversely affects the lifespan. At this time, as a polycyclic ring with low triplet energy, it may be a tetracene, pyrene, benzoanthracene, or perylene group, and a triphenylene group with high triplet energy causes reverse intersystem transition and adversely affects the lifespan. Exclude.

In particular, when L or X is pyrene, excitons not used in the boron core structure as the core structure of the existing blue fluorescent material are more likely to be used for light emission in the pyrene core, thereby increasing the luminous efficiency.

Since the light emitting body of the present invention has little Stokes change, it is possible to select a stable host having a relatively low triplet energy compared to a general blue fluorescent material, which leads to an extension of the lifespan of the organic light emitting diode.

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

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents. For example, the "substituent to which two or more substituents are connected" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, and the like.

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. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferable that it has 1-10 carbon atoms. Specific examples include a methyl group; ethyl group; Profile group; n-propyl group; isopropyl group; butyl group; n-butyl group; isobutyl group; tert-butyl group; sec-butyl group; 1-methylbutyl group; 1-ethylbutyl group; pentyl group; n-pentyl group; isopentyl group; neopentyl group; tert-pentyl group; hexyl group; n-hexyl group; 1-methylpentyl group; 2-methylpentyl group; 4-methyl-2-pentyl group; 3,3-dimethylbutyl group; 2-ethylbutyl group; heptyl group; n-heptyl group; 1-methylhexyl group; cyclopentylmethyl group; cyclohexylmethyl group; octyl group; n-octyl group; tert-octyl group; 1-methylheptyl group; 2-ethylhexyl group; 2-propylpentyl group; n-nonyl group; 2,2-dimethylheptyl group; 1-ethylpropyl group; 1,1-dimethylpropyl group; isohexyl group; 2-methylpentyl group; 4-methylhexyl group; 5-methylhexyl group, and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and more preferably has 3 to 20 carbon atoms. Specifically, a cyclopropyl group; cyclobutyl group; cyclopentyl group; 3-methylcyclopentyl group; 2,3-dimethylcyclopentyl group; cyclohexyl group; 3-methylcyclohexyl group; 4-methylcyclohexyl group; 2,3-dimethylcyclohexyl group; 3,4,5-trimethylcyclohexyl group; 4-tert-butylcyclohexyl group; cycloheptyl group; There is a cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferable that it has 1 to 10 carbon atoms. Specifically, a methoxy group; ethoxy group; n-propoxy group; isopropoxy group; i-propyloxy group; n-butoxy group; isobutoxy group; tert-butoxy group; sec-butoxy group; n-pentyloxy group; neopentyloxy group; isopentyloxy group; n-hexyloxy group; 3,3-dimethylbutyloxy group; 2-ethylbutyloxy group; n-octyloxy group; n-nonyloxy group; n-decyloxy group; benzyloxy group; It may be a p-methylbenzyloxy group, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; an alkylamine group; N-alkylarylamine group; arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of 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 a methylamine group; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; naphthylamine group; biphenylamine group; anthracenylamine group; 9-methylanthracenylamine group; diphenylamine group; N-phenylnaphthylamine group; ditolylamine group; N-phenyltolylamine group; triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group and the like, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiRjRkRl, wherein Rj, Rk and Rl are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically a trimethylsilyl group; triethylsilyl group; t-butyldimethylsilyl group; vinyl dimethyl silyl group; propyldimethylsilyl group; triphenylsilyl group; diphenylsilyl group; There is a phenylsilyl group, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms. The aryl group may be monocyclic or polycyclic. When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. More specifically, it is preferable that it has 6-20 carbon atoms. Specifically, the monocyclic aryl group includes a phenyl group; biphenyl group; It may be a terphenyl group, and the like, but is not limited thereto. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms, and more specifically, it is preferable that it has 10 to 20 carbon atoms. Specifically, the polycyclic aryl group includes a naphthyl group; anthracenyl group; phenanthryl group; triphenyl group; pyrenyl group; phenalenyl group; perylenyl group; chrysenyl group; It may be a fluorenyl group, but is not limited thereto.

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

In the present specification, the meaning of "to form a ring by combining adjacent groups with each other" among the substituents means a substituted or unsubstituted hydrocarbon ring by combining adjacent groups with each other; Or it means to form a substituted or unsubstituted heterocyclic ring.

In the present specification, the ring is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocyclic ring.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or a condensed ring of an aromatic and an aliphatic group, and may be selected from the cycloalkyl group or the aryl group except for the non-monovalent group, and the cycloalkyl group and the aryl group are condensed It can be a ring.

In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from among the examples of the aryl group except for those that are not monovalent.

In the present specification, the heterocycle includes atoms other than carbon and one or more heteroatoms, and specifically, the heterocyclic atoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocyclic ring may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from the following examples of heteroaryl groups except for non-monovalent ones.

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

In the present specification, the heteroaryl group includes one or more atoms other than carbon, that is, 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 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group; furanyl group; pyrrole group; imidazolyl group; thiazolyl group; oxazolyl group; oxadiazolyl group; pyridyl group; bipyridyl group; pyrimidyl group; triazinyl group; triazolyl group; acrydyl group; pyridazinyl group; pyrazinyl group; quinolinyl group; quinazolinyl group; quinoxalinyl group; phthalazinyl group; pyrido pyrimidyl group; pyrido pyrazinyl group; pyrazino pyrazinyl group; isoquinolinyl group; indolyl group; carbazolyl group; benzoxazolyl group; benzimidazolyl group; benzothiazolyl group; benzocarbazolyl group; benzothiophene group; dibenzothiophene group; benzofuranyl group; a phenanthroline group; isoxazolyl group; thiadiazolyl group; There is a phenothiazinyl group and a dibenzofuranyl group, but is not limited thereto.

In the exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-6.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-1 to 1-6, L, X, R, R1 to R3, and a to c are the same as defined in Formula 1 above.

In an exemplary embodiment of the present specification, R1 and R2 are hydrogen.

In the exemplary embodiment of the present specification, at least one of the two or more R1 and the two or more R2 may each independently combine with an adjacent group to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, at least one of the two or more R1 and the two or more R2 may each independently combine with an adjacent group to form a substituted or unsubstituted hydrocarbon ring.

In an exemplary embodiment of the present specification, at least one of the two or more R1 and the two or more R2 may each independently combine with an adjacent group to form a hydrocarbon ring.

In an exemplary embodiment of the present specification, at least one of the two or more R1, and the two or more R2 are each independently combined with an adjacent group to form a benzene ring; Or it may form a cyclohexane ring.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 3 to 5 below.

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 3 to 5, A, Y1, Y2, R3, c, L and X are the same as defined in Formula 1.

In the exemplary embodiment of the present specification, A is B.

In the exemplary embodiment of the present specification, A is P.

In an exemplary embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently represents NR, O, or S.

In an exemplary embodiment of the present specification, Y1 and Y2 are NR.

In the exemplary embodiment of the present specification, Y1 and Y2 are O.

In the exemplary embodiment of the present specification, Y1 and Y2 are S.

In an exemplary embodiment of the present specification, L is a direct bond, a divalent tetracene group, a divalent pyrene group, a divalent benzoanthracene group, or a divalent perylene group.

In an exemplary embodiment of the present specification, L is any one selected from the following substituents.

The dotted line indicates a portion connected to the core.

The Rb to Rh are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

bb is an integer from 0 to 10,

cc and dd are each an integer from 0 to 4,

ee and ff are each an integer from 0 to 5,

gg is an integer from 0 to 2,

hh is an integer from 0 to 7,

cc+dd≤8,

ee+ff≤10,

gg+hh≤9.

In an exemplary embodiment of the present specification, Rb to Rh are the same as or different from each other, and each independently represents hydrogen or deuterium.

In the exemplary embodiment of the present specification, Rb to Rh are hydrogen.

In one embodiment of the present specification, L is divalent pyrene. Specifically, when L is a divalent pyrene, excitons not used in the core structure including B or P of Formula 1 are used for light emission in the pyrene, thereby increasing the luminous efficiency.

이다.In an exemplary embodiment of the present specification, L is

to be.

In an exemplary embodiment of the present specification, X is hydrogen, a phenyl group, a tetracenyl group, a pyrenyl group, a benzoanthracenyl group, a perylenyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylamine group, a substituted Or an unsubstituted heteroaryl group, or Formula 2 above.

In an exemplary embodiment of the present specification, X is hydrogen, a phenyl group, a substituted or unsubstituted C 1 to C 10 alkyl group, 6 to 30 C arylamine group, or a substituted or unsubstituted C 3 to C 30 heteroaryl group , or Formula 2 above.

In an exemplary embodiment of the present specification, X is hydrogen; phenyl group; methyl group; ethyl group; Profile group; isopropyl group; butyl group; terbutyl group; an amine group substituted with a phenyl group, a biphenyl group, a terphenyl group, an anthracene group, a phenanthrene group, or a pyrene group; dibenzofuran group; dibenzothiophene group; benzonaphthofuran group; benzonaphthothiophene group; triazine group; pyrimidine group; pyridine group; a carbazole group unsubstituted or substituted with an alkyl group or an aryl group; or Formula 2 above.

In an exemplary embodiment of the present specification, X is hydrogen, a methyl group, a terbutyl group, a phenyl group, an amine group substituted with a phenyl group, a benzonaphthofuran group, a benzonaphthothiophene group, a carbazole group substituted with a terbutyl group, or A carbazole group substituted with a phenyl group, or Formula 2 above.

In an exemplary embodiment of the present specification, X is any one selected from the following substituents, or is represented by Formula 2 above.

The dotted line is a portion coupled to L.

In an exemplary embodiment of the present specification, X is a phenyl group; benzonaphthofuran group; benzonaphthothiophene group; Or represented by the above formula (2).

In the exemplary embodiment of the present specification, the structure of Formula 2 is the same as the core structure of Formula 1.

In the exemplary embodiment of the present specification, A' in Formula 2 is the same as A in Formula 1.

In the exemplary embodiment of the present specification, Y1' and Y2' of Formula 2 are the same as Y1 and Y2 of Formula 1.

In the exemplary embodiment of the present specification, R1' to R3' of Formula 2 are the same as R1 to R3 of Formula 1.

In the exemplary embodiment of the present specification, a' to c' of Formula 2 are the same as a to c of Formula 1;

In an exemplary embodiment of the present specification, R and R1 to R3 are the same as or different from each other, and each independently hydrogen, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or an unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, R1 to R3 are hydrogen.

In an exemplary embodiment of the present specification, R3 is hydrogen.

In an exemplary embodiment of the present specification, R is hydrogen, a nitrile group, a halogen group, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 1 to C 10 alkoxy group, a substituted or unsubstituted A silyl group having 1 to 10 carbon atoms, an amine group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms, a phosphine oxide group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted C6 to 30 aryl group an aryl group, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

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

In an exemplary embodiment of the present specification, R, R1 and R2 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C30 It is an aryl group.

In an exemplary embodiment of the present specification, R, R1 and R2 are the same as or different from each other, and each independently hydrogen, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracene group , or a phenanthrene group,

The methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracene group, or phenanthrene group is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R, R1 and R2 are the same as or different from each other, and each independently hydrogen, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a terbutyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracene group, or a phenanthrene group;

The methyl group, ethyl group, propyl group, isopropyl group, butyl group, terbutyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracene group, or phenanthrene group is an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 6 to 30 carbon atoms. It is unsubstituted or substituted with an aryl group.

In an exemplary embodiment of the present specification, R, R1 and R2 are the same as or different from each other, and each independently represents hydrogen, a methyl group, a terbutyl group, a phenyl group, a biphenyl group, or a terphenyl group,

The methyl group, terbutyl group, phenyl group, biphenyl group, or terphenyl group is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R, R1 and R2 are the same as or different from each other, and each independently hydrogen, a methyl group, a terbutyl group, a phenyl group, a phenyl group substituted with a phenyl group, a phenyl group substituted with a terbutyl group, a biphenyl group , or a terphenyl group.

In an exemplary embodiment of the present specification, R and R1, or R and R2 are bonded to each other to form a ring including N, O, or S.

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

In the above structural formula, L and X are the same as defined in Formula 1 above.

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

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

The organic light emitting device of the present invention includes a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers may include the aforementioned compound.

For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2 , but is not limited thereto.

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

2 is a substrate 1, a first electrode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, a light emitting layer 8, electron injection and transport at the same time The structure of the organic light emitting device in which the layer 9 and the second electrode 4 are sequentially stacked is illustrated.

1 and 2 illustrate an organic light emitting device, but is not limited thereto.

In an exemplary embodiment of the present invention, the organic material layer includes an emission layer, and the emission layer includes the compound of Formula 1 above.

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

In an exemplary embodiment of the present invention, the organic material layer includes an emission layer, and the emission layer includes a host and a dopant in a weight ratio of 97:3 to 95:5.

In an exemplary embodiment of the present invention, the organic material layer includes an emission layer, and the emission layer includes a host and a dopant in a weight ratio of 95:5.

In an exemplary embodiment of the present invention, the organic material layer includes an emission layer, and the emission layer includes the compound of Formula 1 as a dopant.

In an exemplary embodiment of the present invention, the organic material layer includes an emission layer, and the emission layer includes the compound of Formula 1 as a blue dopant.

In an exemplary embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer further includes a host.

In an exemplary embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer further includes a blue host.

In an exemplary embodiment of the present invention, the light emitting layer further includes a host compound, and the host compound is an anthracene-based compound.

In an exemplary embodiment of the present invention, the organic material layer may include a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, or a layer that simultaneously injects and transports electrons.

In an exemplary embodiment of the present invention, the organic material layer includes a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is The compound of Formula 1 may be included.

In an exemplary embodiment of the present invention, the organic material layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons, and the electron injection layer, the electron transport layer, or a layer that simultaneously injects and transports electrons The compound of Formula 1 may be included.

In an exemplary embodiment of the present invention, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the compound of Formula 1 above.

For example, the organic light emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, to form a metal or a conductive metal oxide or an alloy thereof on a substrate. to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an organic material layer including the compound of Formula 1 thereon, a material that can be used as a cathode is deposited thereon It can be manufactured by In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

As the anode material, a material having a large work function is generally preferred 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, 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 : Combinations of metals and oxides such as Sb; poly(3-methyl compound), poly[3,4-(ethylene-1,2-dioxy) compound] (PEDT), polypyrrole, and conductive polymers such as polyaniline, but are not limited thereto.

The cathode 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; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, and conductive polymers based on polyaniline and polycompounds, but is not limited thereto.

As the hole transport material, a material capable of transporting holes from an anode or a hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

When the layer containing Formula 1 of the present invention is the light emitting layer, the light emitting material may be included in the light emitting layer including Formula 1 or may be included in a light emitting layer other than the light emitting layer including the compound of Formula 1 above.

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

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that at least one of the organic material layers is formed using the compound.

The present specification also provides a method of manufacturing an organic light emitting device formed using the compound.

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

The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. do. Specific examples include Al complex of 8-hydroxyquinoline; complexes comprising Alq3; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.

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

The material of the layer for simultaneously injecting and transporting the electrons may include the aforementioned material for the electron transport layer or the material for the electron injection layer. In addition, the layer for simultaneously injecting and transporting electrons may further include a metal complex.

The material of the layer for simultaneously injecting and transporting the electrons may include the aforementioned material for the electron transport layer or the material for the electron injection layer. In addition, the layer for simultaneously injecting and transporting electrons may further include lithium quinolate.

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

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

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

A method of preparing the compound of Formula 1 and manufacturing an organic light emitting device using the same will be described in detail in Examples below. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

<Synthesis example>

Synthesis Example 1. Synthesis of compound 1

Synthesis of Intermediate A-1

2-bromo-5-chloro-1,3-diple in phenol (24.6 g, 0.260 mol), potassium carbonate (36.0 g, 0.260 mol) and N-methylpyrrolidone (NMP, 500 mL) at room temperature under nitrogen atmosphere Lorobenzene (29.6 g, 0.130 mol) was added and stirred at 120° C. for 24 hours. After that, NMP was distilled under reduced pressure, and then toluene was added. Silica gel was filtered using a short path column, and the solvent was distilled under reduced pressure to obtain A-1. (48.4g)

Synthesis of Intermediate A-2

A-1 (8.2 g, 21.9 mmol) was dissolved in 90 mL of o-xylene, and 9.2 mL (2.5 M) of n-butyllithium was slowly added dropwise at 0 °C. After stirring at 70 °C for 4 hours, boron tribromide (2.6 mL, 27.5 mmol) was added at -40 °C. After stirring while raising the temperature to room temperature over 1 hour, N,N-diisopropylethylamine (N,N-diisopropylethylamine) (9.0 mL, 45.8 mmol) was added dropwise at 0° C., followed by stirring at 120° C. for 5 hours. . After extraction with dichloromethane, the organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled under reduced pressure. Next, column chromatography was performed with a 1:1 eluent in hexane:ethyl acetate to obtain A-2 (3.0 g). MS:[M+H] ⁺ = 305.

Synthesis of compound 1

A-2 (3.8 g), (6-phenylpyren-1-yl)boronic acid (3.5 g), palladium acetate (0.066 g), potassium phosphate (3.1 g), dicyclohexyl (2',6'-dime The flask containing toxy-[1,1'-biphenyl]-2-yl)phosphine (0.24 g), cyclopentylmethyl ether (30 mL) and water (6 mL) was refluxed and stirred for 6 hours. After extraction with dichloromethane, the organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled under reduced pressure. Next, column chromatography was performed with hexane:ethyl acetate as a 1:1 eluent to obtain Compound 1 (3.0 g). MS:[M+H]+ = 547.

Synthesis Example 2. Synthesis of compound 2

Instead of (6-phenylpyren-1-yl)boronic acid (3.5g) in the synthesis of compound 1, (6-(naphtho[2,3-b]benzofuran-3-yl)pyren-1-yl)boron Compound 2 was obtained in the same manner except that an acid (5.0 g) was used. MS:[M+H] ⁺ = 687.

Synthesis Example 3. Synthesis of compound 3

Synthesis of Intermediate B-1

2-Bromo-5- in 4-(tert-butyl)phenol (39.1 g, 0.260 mol), potassium carbonate (36.0 g, 0.260 mol) and N-methylpyrrolidone (NMP, 500 mL) at room temperature under nitrogen atmosphere Chloro-1,3-difluorobenzene (29.6 g, 0.130 mol) was added and the mixture was heated and stirred at 120 °C for 24 hours. After that, NMP was distilled under reduced pressure, and then toluene was added. Silica gel was filtered using a short path column, and the solvent was distilled under reduced pressure to obtain B-1. (49.6g)

Synthesis of Intermediate B-2

In the synthesis method of Intermediate A-2, B-2 was prepared in the same manner except that B-1 was used instead of A-1.

Synthesis of compound 3

B-2 (4.4 g), (6-phenylpyren-1-yl)boronic acid (3.5 g), palladium acetate (0.066 g), potassium phosphate (3.1 g), dicyclohexyl (2', 6'-dime The flask containing toxy-[1,1'-biphenyl]-2-yl)phosphine (0.24 g), cyclopentyl methyl ether (30 mL) and water (6 mL) was refluxed and stirred for 6 hours. After extraction with dichloromethane, the organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled under reduced pressure. Next, column chromatography was performed with hexane:ethyl acetate as a 1:1 eluent to obtain compound 3 (3.0 g). MS:[M+H] ⁺ = 659.

Synthesis Example 4. Synthesis of compound 4

Instead of (6-phenylpyren-1-yl)boronic acid (3.5g) in the synthesis of compound 3, (6-(naphtho[2,3-b]benzofuran-3-yl)pyren-1-yl)boron Compound 4 was obtained by the same preparation except that an acid (5.0 g) was used. MS:[M+H] ⁺ = 687

Synthesis Example 5. Synthesis of compound 5

A-2 (3.8 g), pyrene-1,6-diyldiboronic acid (1.8 g), palladium acetate (0.066 g), potassium phosphate (3.1 g), dicyclohexyl The flask containing (2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (0.24 g), cyclopentyl methyl ether (30 mL) and water (6 mL) was refluxed and , and stirred for 6 h. After extraction with dichloromethane, the organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled under reduced pressure. Next, column chromatography was performed with a 1:1 developing solution in hexane:ethyl acetate to obtain compound 5 (3.2 g). MS:[M+H]+ = 739.

Synthesis Example 6. Synthesis of compound 6

Synthesis of Intermediate C-1

2-Bromo-5-chloro-1,3 in 1-naphthol (37.5 g, 0.260 mol), potassium carbonate (36.0 g, 0.260 mol) and N-methylpyrrolidone (NMP, 500 mL) at room temperature under nitrogen atmosphere - Difluorobenzene (29.6 g, 0.130 mol) was added and stirred at 120 °C for 24 hours. After that, NMP was distilled under reduced pressure, and then toluene was added. It was filtered using a silica gel short path column, and the solvent was distilled under reduced pressure to obtain C-1. (39.6g)

Synthesis of Intermediate C-2

C-1 (10.4 g, 21.9 mmol) was dissolved in 90 mL of o-xylene, and 9.2 mL (2.5 M) of n-butyllithium was slowly added dropwise at 0°C. After stirring at 70 °C for 4 hours, boron tribromide (2.6 mL, 27.5 mmol) was added at -40 °C. After stirring while raising the temperature to room temperature over 1 hour, N,N-diisopropylethylamine (N,N-diisopropylethylamine) (9.0 mL, 45.8 mmol) was added dropwise at 0° C., followed by stirring at 120° C. for 6 hours. After extraction with dichloromethane, the organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled under reduced pressure. Next, column chromatography was performed using hexane:ethyl acetate as a 1:1 developing solution to obtain C-2 (3.8 g). MS:[M+H] ⁺ = 405.

Synthesis of compound 6

C-2 (5.0 g), (6-phenylpyren-1-yl)boronic acid (3.5 g), palladium acetate (0.066 g), potassium phosphate (3.1 g), dicyclohexyl (2', 6'-dime The flask containing toxy-[1,1'-biphenyl]-2-yl)phosphine (0.24 g), cyclopentylmethyl ether (30 mL) and water (6 mL) was refluxed and stirred for 6 hours. After extraction with dichloromethane, the organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled under reduced pressure. Next, column chromatography was performed with hexane:ethyl acetate as a 1:1 eluent to obtain compound 6 (3.4 g). MS:[M+H] ⁺ = 647.

Synthesis Example 7. Synthesis of compound 7

Synthesis of Intermediate D-1

In the synthesis of Intermediate A-1, in the same manner as D-1, except that 5,6,7,8-tetrahydronaphthalen-1-ol (5,6,7,8-tetrahydronaphthalen-1-ol) was used instead of phenol. (47.5 g) was obtained.

Synthesis of Intermediate D-2

D-1 (10.6 g, 21.9 mmol) was dissolved in 90 mL of o-xylene, and 9.2 mL (2.5 M) of n-butyllithium was slowly added dropwise at 0 °C. After stirring at 70 °C for 4 hours, boron tribromide (2.6 mL, 27.5 mmol) was added at -40 °C. After stirring while raising the temperature to room temperature over 1 hour, N,N-diisopropylethylamine (9.0 mL, 45.8 mmol) was added dropwise at 0° C., followed by stirring at 120° C. for 6 hours. After extraction with dichloromethane, the organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled under reduced pressure. Next, column chromatography was performed with a 1:1 eluent in hexane:ethyl acetate to obtain D-2 (4.0 g). MS:[M+H] ⁺ = 413.

Synthesis of compound 7

D-2 (5.0 g), (6-phenylpyren-1-yl)boronic acid (3.5 g), palladium acetate (0.066 g), potassium phosphate (3.1 g), dicyclohexyl (2', 6'-dime The flask containing toxy-[1,1'-biphenyl]-2-yl)phosphine (0.24 g), cyclopentylmethyl ether (30 mL) and water (6 mL) was refluxed and stirred for 6 hours. After extraction with dichloromethane, the organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled under reduced pressure. Next, column chromatography was performed with a 1:1 eluent in hexane:ethyl acetate to obtain compound 7 (3.8 g). MS:[M+H] ⁺ = 655.

Synthesis Example 8. Synthesis of compound 8

Synthesis of Intermediate E-1

2-bromo-5-chloro-1,3 in benzenethiol (28.7 g, 0.260 mol), potassium carbonate (36.0 g, 0.260 mol) and N-methylpyrrolidone (NMP, 500 mL) at room temperature under nitrogen atmosphere - Difluorobenzene (29.6 g, 0.130 mol) was added and stirred at 120 °C for 24 hours. After that, NMP was distilled under reduced pressure, and then toluene was added. Silica gel was filtered using a short path column, and the solvent was distilled under reduced pressure to obtain E-1. (44.8g)

Synthesis of Intermediate E-2

E-1 (8.9 g, 21.9 mmol) was dissolved in 90 mL of o-xylene, and 9.2 mL (2.5 M) of n-butyllithium was slowly added dropwise at 0 °C. After stirring at 70 °C for 4 hours, boron tribromide (2.6 mL, 27.5 mmol) was added at -40 °C. After stirring while raising the temperature to room temperature over 1 hour, N,N-diisopropylethylamine (9.0 mL, 45.8 mmol) was added dropwise at 0° C., followed by stirring at 120° C. for 5 hours. After extraction with dichloromethane, the organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled under reduced pressure. Next, column chromatography was performed with a 1:1 eluent in hexane:ethyl acetate to obtain E-2 (3.2 g). MS:[M+H] ⁺ = 337.

Synthesis of compound 8

E-2 (3.4 g), pyrene-1,6-diylboronic acid, palladium acetate (0.066 g), potassium phosphate (3.1 g), dicyclohexyl (2', 6'-dimethoxy-[1,1) A flask containing '-biphenyl]-2-yl) phosphine (0.24 g), cyclopentylmethyl ether (30 mL) and water (6 mL) was stirred at reflux temperature for 6 hours. After extraction with dichloromethane, the organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled under reduced pressure. Next, column chromatography was performed with hexane:ethyl acetate as a 1:1 developing solution to obtain compound 8 (1.0 g). MS:[M+H] ⁺ = 803.

<Experimental Example 1>

Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1300 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was 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 thus prepared ITO transparent electrode, the following compound HAT was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer. On it, the following compound HT-A 1000 Å was vacuum-deposited as a first hole transport layer, and then the following compound HT-B 100 Å was deposited as a second hole transport layer. A light emitting layer having a thickness of 200 Å was formed by vacuum deposition of BH-A as a host and Compound 1 as a dopant at a weight ratio of 95:5.

Then, 300Å of the following compound ET-A and the following compound Liq were deposited as a layer for simultaneously injecting and transporting electrons in a 1:1 ratio (weight ratio), and on this, lithium fluoride (LiF) and 1,000 to a thickness of 10Å sequentially An organic light-emitting device was manufactured by depositing aluminum to a thickness of Å to form a cathode.

In the above process, the deposition rate of organic material was maintained at 0.4 ~ 2.0 Å, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 1 Х 10 ^-7 To 5 Х 10 ^-8 torr was maintained, an organic light emitting device was manufactured.

Examples 2 to 8

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the dopant compound shown in Table 1 was used instead of Compound 1 as the light emitting layer material in Example 1.

Comparative Examples 1 to 3

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the dopant compound shown in Table 1 was used instead of Compound 1 as the light emitting layer material in Example 1.

The organic light emitting devices manufactured by Examples 1 to 8 and Comparative Examples 1 to 3 were subjected to the maximum peak position of the EL spectrum at a current density of ^{10 mA/cm 2 using a Keithley 2635B system source meter and a PR670 detector, full width at half maximum (FWHM).} ), the luminous efficiency was measured, and the results are shown in Table 1 below.

dopant
(Light emitting layer) 10mA/cm ² EL max peak
(nm) FWHM
(nm) luminous efficiency
(Cd/A) Example 1 One 462 17 6.9 Example 2 2 462 16 7.1 Example 3 3 460 16 7.5 Example 4 4 460 16 7.3 Example 5 5 461 17 7.1 Example 6 6 462 18 6.8 Example 7 7 462 17 6.6 Example 8 8 462 17 6.8 Comparative Example 1 BD-1 465 19 5.9 Comparative Example 2 BD-2 465 19 6.0 Comparative Example 3 BD-3 467 19 7.0

As shown in Table 1, the devices of Examples 1 to 8 using the compound having the structure of Formula 1 have relatively high efficiency, small full width at half maximum (FWHM) than the devices of Comparative Examples 1 to 3, and have dark blue characteristics. Specifically, Comparative Examples 1 and 2 are compounds in which -LX of the present invention is hydrogen or a phenyl group, respectively, and luminous efficiency compared to the compounds having tetracene, pyrene, benzoanthracene, and perylene as L or X of the present invention It was confirmed that this significantly decreased.

In addition, the compound in which L of Examples 1 to 8 of the present invention is pyrene has a maximum peak of the EL spectrum at a lower wavelength and a narrow full width at half maximum compared to the compound in which L is anthracene of Comparative Example 3, so Comparative Example 3 It has the advantages of higher efficiency and higher purity.

1: Substrate
2: first electrode
3: organic layer
4: second electrode
5: hole injection layer
6: first hole transport layer
7: second hole transport layer
8: light emitting layer
9: A layer that simultaneously injects and transports electrons

Claims (10)

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

In Formula 1,
A is B or P,
Y1 and Y2 are the same as or different from each other and are each independently NR, O, or S;
L is selected from the following structural formulas,

The dotted line means a part connected to the core,
The Rb to Rh are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
bb is an integer from 0 to 10,
cc and dd are each an integer from 0 to 4,
ee and ff are each an integer from 0 to 5,
gg is an integer from 0 to 2,
hh is an integer from 0 to 7,
cc+dd≤8,
ee+ff≤10,
gg+hh≤9,
X is hydrogen, a phenyl group, a tetracenyl group, a pyrenyl group, a benzoanthracenyl group, a perylenyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroaryl group, or represented by the formula (2),
[Formula 2]

In Formula 2,

means a position bonded to L of Formula 1,
A' is B or P;
Y1' and Y2' are the same as or different from each other, each independently represent NR', O, or S, R, R', R1 to R3 and R1' to R3' are the same as or different from each other, and each independently hydrogen, A nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted A cyclic aryl group, or a substituted or unsubstituted heteroaryl group,
may combine with adjacent groups to form a substituted or unsubstituted ring,
a, a' b and b' are each 0 or 1,
c and c' are each 0,
The term "substituted or unsubstituted" refers to deuterium; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents. The compound according to claim 1, wherein Formula 1 is represented by any one of Formulas 1-1 to 1-6:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-1 to 1-6, L, X, R, R1 to R3, and a to c are the same as defined in Formula 1 above. The compound according to claim 1, wherein R, R1 and R2 are the same as or different from each other, and each independently represents hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The method according to claim 1, wherein X is hydrogen, a phenyl group, a substituted or unsubstituted C 1 to C 10 alkyl group, 6 to 30 C arylamine group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, or the above formula 2. The compound of which it is 2. The compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:

In the above structural formula, L and X are as defined in Formula 1 above. a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound of any one of claims 1 to 5. light emitting element. The organic light-emitting device of claim 6 , wherein the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound. The organic light emitting device according to claim 6, wherein the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound. The organic light-emitting device of claim 6 , wherein the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the compound. The organic light-emitting device of claim 6 , wherein the organic material layer includes an emission layer, and the emission layer includes the compound.

Images