KR102225901B1 - Multicyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a polycyclic compound of Formula 1 and an organic light-emitting device including the same.

Description

A polycyclic compound and an organic light-emitting device including the same TECHNICAL FIELD [0002]

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

In the present specification, an organic light-emitting device is a light-emitting device using an organic semiconductor material, and requires an exchange of holes and/or electrons between an electrode and an organic semiconductor material. Organic light emitting devices can be divided into two types as follows according to the principle of operation. First, excitons are formed in the organic material layer by photons introduced into the device from an external light source, and these excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes, and used as a current source (voltage source). It is a type of light emitting device. The second is a light emitting device in which holes and/or electrons are injected into an organic semiconductor material layer forming an interface with the electrode by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic light-emitting device using the organic light-emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of 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 such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows. These organic light emitting devices are known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.

Materials used as the organic material layer in the organic light-emitting device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions. Light-emitting materials include blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary to realize better natural colors according to the light-emitting color.

In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a luminescent material. The principle is that when a small amount of a dopant having an energy band gap smaller than that of a host constituting the light emitting layer and having excellent light emission efficiency is mixed in a light emitting layer, excitons generated from the host are transported as a dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

In order to fully exhibit the excellent characteristics of the above-described organic light emitting device, materials that form the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc., are supported by stable and efficient materials. The development of new materials continues to be required.

Korean Patent Publication No. 2011-108575

In the present specification, a polycyclic compound and an organic light emitting device including the same are described.

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

[Formula 1]

In Formula 1,

R1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

X1 and X2 are the same as or different from each other, and each independently O, S, S(=O), C(=O), SO ₂ , NRa, CRbRc or SiRdRe,

Ra, Rb, Rc, Rd, Re and R2 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

n1 and n2 are each an integer of 0 to 6, and when n1 and n2 are each 2 or more, the substituents in 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 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 polycyclic compound described above.

The compounds described herein can be used as a material for an organic material layer of an organic light-emitting device. In the case of manufacturing an organic light-emitting device including the compound according to at least one embodiment, an organic light-emitting device having low voltage, high efficiency and long life can be obtained, and when the compound of the present invention is included in the emission layer of the organic light-emitting device, high An organic light-emitting device having a color gamut can be manufactured.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
FIG. 2 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole transport layer 5, a light-emitting layer 3, an electron transport layer 6, and a cathode 4.

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

The present specification provides a polycyclic compound represented by the following formula (1). When the polycyclic compound of Formula 1 is used in the organic material layer of the organic light-emitting device, the driving voltage of the organic light-emitting device is lowered, and efficiency and lifespan characteristics are improved.

[Formula 1]

In Formula 1,

R1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

X1 and X2 are the same as or different from each other, and each independently O, S, S(=O), C(=O), SO ₂ , NRa, CRbRc or SiRdRe,

Ra, Rb, Rc, Rd, Re and R2 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

n1 and n2 are each an integer of 0 to 6, and when n1 and n2 are each 2 or more, the substituents in parentheses are the same or different from each other.

In order to exhibit excellent light emitting characteristics in an organic light emitting device, the performance of the light emitting layer material must be improved, and in particular, the quantum efficiency of the dopant material must be improved. In addition, it is desirable to minimize the difference between the absorption region and the emission region of the dopant material.

In order to increase luminous efficiency or quantum efficiency, radiative attenuation should be maximized when transitioning from an excited state to a ground state. In general, in the case of a light-emitting material composed of an expanded form of π conjugation, ^{the transition probability of π *} → π is high, so that the radiative attenuation ratio is high, and as a result, fluorescence quantum efficiency is excellent. For this example, anthracene or a pyrene derivative is a material having excellent quantum efficiency and is widely used as a material for a light emitting layer of an OLED device. Therefore, in the present invention, in order to secure excellent quantum efficiency characteristics, a π conjugated molecule was designed, and in order to control the expansion of the conjugation, nitrogen having an electron-giving characteristic and a boron atom having an electron-accepting characteristic were properly placed in the molecule. A material having excellent luminescence properties was prepared by controlling the length of the conjugation. An organic light-emitting device having excellent light-emitting characteristics was implemented by using such a material as a light-emitting dopant.

However, since boron-introduced compounds generally exhibit oxygen or moisture-sensitive properties, stabilization is achieved by introducing a substituent having a large steric hindrance to a phenyl group directly connected to boron. This characteristic is a phenomenon that occurs because the Lewis base characteristic of boron is strong.In the present invention, for stabilization of boron, three nitrogens having a large electron giving effect to the phenyl ring ortho and the para position connected to boron are introduced to increase the stability of the molecule. I did it. That is, the stabilization of boron was attempted by supplying electrons of nitrogen. The advantage of such a light-emitting material is that it is possible to minimize decomposition of light-emitting molecules during thermal decomposition or driving the device, rather than introducing an alkyl group having a large steric hindrance, and as a result, an organic light-emitting device having a long life can be implemented.

The difference between the absorption and emission areas of the light-emitting material (generally known as Stokes' movement) affects the selection of the host material to use the dopant material and power efficiency, so it is desirable to have a form with as little difference between the absorption and emission areas as possible. . In order to impart such properties, it can be used in various techniques, but among them, when the change of the molecular structure in the transition state and the molecular structure in the ground state is minimized, the difference in Stokes' movement is very small. Therefore, in the present invention, in order to maximize these properties, the difference in Stokes' movement could be minimized by making the molecular structure of the portion where HOMO and LUMO are formed very solid.

"는 결합되는 위치를 의미한다.In this specification, "

"Means the position to be combined.

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

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

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

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two 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; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents. For example, "a substituent to which two or more substituents are connected" may be a t-butylphenyl group. That is, the t-butylphenyl group may be a substituted aryl group or may be interpreted as a substituent in which a t-butyl group and a phenyl group are connected.

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

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

In the present specification, the silyl group may be represented by the formula of _{-SiY a} Y _b Y _{c , wherein Y a} , Y _b and Y _c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc. Does not.

In the present specification, the boron group may be represented by the formula of _{-BY d} Y _{e , wherein Y d} and Y _e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the boron group includes a trimethyl boron group, a triethyl boron group, a tert-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-oxy And the like, but are not limited to these.

In the present specification, the alkoxy group may be a straight chain, branched chain, or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but may have 1 to 40 carbon atoms, and may have 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -Hexyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc. may be, but is not limited thereto.

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

In the present specification, the amine group is -NH ₂ ; Alkylamine group; Arylalkylamine group; Arylamine group; Arylheteroarylamine group; It may be selected from the group consisting of an alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60.

In the present specification, the number of carbon atoms in the alkylamine group is not particularly limited, but may be 1 to 40, and according to an embodiment, may be 1 to 20. Specific examples of the alkylamine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group.

In the 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.

Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a biphenylphenylamine group, a dibiphenylamine group, and fluorine. Nilphenylamine 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, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.

In the present specification, an arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group.

In the present specification, an arylalkylamine group means an aryl group and an amine group substituted with an alkyl group.

In the present specification, an alkylheteroarylamine group means an amine group substituted with an alkyl group and a heteroaryl group.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

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

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

Spirofluorenyl groups such as,

(9,9-dimethylfluorenyl group), and

It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si and Se as a hetero atom, and may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic The number of carbon atoms may be, but the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group. , Xanthene, thioxanthene, and the like, but are not limited thereto.

In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroaryl group is aromatic.

In the present specification, the description of the aryl group described above may be applied except that the arylene group is a divalent group.

In this specification, "adjacent" The group may mean a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on an atom in which the corresponding substituent is substituted. For example, two substituents substituted with an ortho position in a benzene ring and two substituents substituted with the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other. In addition, when X1 and/or X2 in Formula 1 herein is CRbRc, Rb and Rc may be interpreted as "adjacent" to each other.

In the present specification, in a substituted or unsubstituted ring formed by bonding of adjacent groups to each other, "ring" is a hydrocarbon ring; Or it means a heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or an aryl group, except that it is a divalent group.

In the present specification, description of an aryl group may be applied except that the aromatic hydrocarbon ring is divalent.

In the present specification, the heterocycle may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and the description of the heterocyclic group may be applied except that it is a divalent group.

In the present specification, the description of the heteroaryl group may be applied except that the aromatic heterocycle is a divalent group.

In the present specification, the aryl group in the aryloxy group may be described above with respect to the aryl group.

According to an exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and are each independently O, S, S(=O), C(=O), SO ₂ , NRa, CRbRc, or SiRdRe.

In the exemplary embodiment of the present specification, X1 and X2 are O.

In the exemplary embodiment of the present specification, X1 and X2 are S.

"와 같은 구조를 갖는다. In the exemplary embodiment of the present specification, X1 and X2 are S(=O). The "S(=O)" refers to a state in which an S atom and an O atom are double bonded, and more specifically, "

It has the same structure as ".

"와 같은 구조를 갖는다.In the exemplary embodiment of the present specification, X1 and X2 are SO ₂ . The "SO _2" refers to a state in which two O atoms are bonded to an S atom, each of which is a double bond. Specifically "

It has the same structure as ".

"와 같은 구조를 갖는다. In the exemplary embodiment of the present specification, X1 and X2 are C(=O). The C (=O) refers to a state in which a C atom and an O atom are double bonded, and more specifically "

It has the same structure as ".

In the exemplary embodiment of the present specification, X1 and X2 are NRa.

In the exemplary embodiment of the present specification, X1 and X2 are CRbRc.

In the exemplary embodiment of the present specification, X1 and X2 are SiRdRe.

In the exemplary embodiment of the present specification, any one of X1 and X2 is O, and the other is CRbRc.

In the exemplary embodiment of the present specification, any one of X1 and X2 is C(=O), and the other is CRbRc.

In the exemplary embodiment of the present specification, any one of X1 and X2 is C(=O), and the other is O.

In the exemplary embodiment of the present specification, any one of X1 and X2 is O, and the other is S.

X1 and X2 may be the same or different, and if a symmetric molecule in which the same group is introduced into X1 and X2 has the possibility to reduce the width of the emission spectrum, it is possible to secure a high color gamut when applied to an organic light emitting device. There is an advantage.

According to an exemplary embodiment of the present specification, the Ra, Rb, Rc, Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C40 alkyl group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 2 to 60 carbon atoms.

According to another exemplary embodiment, the Ra, Rb, Rc, Rd and Re are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ra is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

According to another exemplary embodiment, Ra is an alkyl group having 1 to 20 carbon atoms; Aryl group having 6 to 30 carbon atoms; Or it is a C2-C30 heterocyclic group.

According to an exemplary embodiment of the present specification, Rb and Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or bonded to each other to form a substituted or unsubstituted ring having 2 to 60 carbon atoms.

According to another exemplary embodiment, the Rb and Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms by bonding to each other; Or a substituted or unsubstituted C2 to C60 heterocycle is formed.

In another exemplary embodiment, Rb and Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group containing at least one of O, S and N as a hetero element having 2 to 30 carbon atoms, or a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms by bonding to each other; Or a substituted or unsubstituted hetero element having 2 to 60 carbon atoms to form a heterocycle including at least one of O, S, and N.

According to another exemplary embodiment, the Rb and Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group containing at least one of O, S and N as a hetero element having 2 to 30 carbon atoms, or a substituted or unsubstituted fluorene ring by bonding to each other; Substituted or unsubstituted thioxanthene ring; Or to form a substituted or unsubstituted xanthene ring (xanthene).

In another exemplary embodiment, Rb and Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted fluorene ring by bonding to each other; Substituted or unsubstituted thioxanthene ring; Or to form a substituted or unsubstituted xanthene ring (xanthene).

According to another exemplary embodiment, the Rb and Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group, or a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms by bonding to each other; Or a substituted or unsubstituted hetero element having 2 to 60 carbon atoms to form a heterocycle including at least one of O, S, and N.

In another exemplary embodiment, Rb and Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Or a phenyl group, or bonded to each other to form a fluorene ring; Thioxanthene ring; Or to form xanthene ring (xanthene).

According to an exemplary embodiment of the present invention, Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or bonded to each other to form a substituted or unsubstituted ring having 2 to 60 carbon atoms.

According to another exemplary embodiment, the Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Rd and Re are the same as or different from each other. Each independently hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another exemplary embodiment, Rd and Re are the same as or different from each other. Each independently hydrogen; heavy hydrogen; Phenyl group; Biphenyl group; Or a naphthyl group.

According to an exemplary embodiment of the present specification, Formula 1 may be represented by any one of Formulas 2 to 4 below.

[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,

The definitions of R1 to R6, n1 and n2 are as defined in Formula 1,

X3 to X5 are the same as or different from each other, and each independently O, S, S(=O), C(=O), SO ₂ , NRa' or SiRd'Re',

Ra', Rd' and Re' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar1 to Ar6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, X3 and X4 are the same as or different from each other, and are each independently O, S, S(=O), C(=O), SO ₂ , NRa', or SiRd'Re'. .

In the exemplary embodiment of the present specification, X3 and X4 are O.

In the exemplary embodiment of the present specification, X3 and X4 are S.

In the exemplary embodiment of the present specification, X3 and X4 are SO ₂ .

In the exemplary embodiment of the present specification, X3 and X4 are S(=O).

In the exemplary embodiment of the present specification, any one of X3 and X4 is O, and the other is S or C(=O).

According to an exemplary embodiment of the present specification, X3 and X4 are SiRd'Re', and definitions of Rd' and Re' are as described above.

"와 같은 구조를 갖는다. In the exemplary embodiment of the present specification, X3 and X4 are S(=O). The "S(=O)" refers to a state in which an S atom and an O atom are double bonded, and more specifically, "

It has the same structure as ".

"와 같은 구조를 갖는다.In the exemplary embodiment of the present specification, X3 and X4 are SO ₂ . The "SO _2" refers to a state in which two O atoms are bonded to an S atom, each of which is a double bond. Specifically "

It has the same structure as ".

According to an exemplary embodiment of the present specification, X5 is O or C(=O).

According to an exemplary embodiment of the present specification, Ra', Rd', and Re' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C40 alkyl group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

According to another exemplary embodiment, the Ra', Rd', and Re' are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ra' is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

According to another exemplary embodiment, Ra' is an alkyl group having 1 to 20 carbon atoms; Aryl group having 6 to 30 carbon atoms; Or it is a C2-C30 heterocyclic group.

According to an exemplary embodiment of the present invention, Rd' and Re' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

According to another exemplary embodiment, Rd' and Re' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Rd' and Re' are the same as or different from each other. Each independently hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another exemplary embodiment, Rd' and Re' are the same as or different from each other. Each independently hydrogen; heavy hydrogen; Phenyl group; Biphenyl group; Or a naphthyl group.

According to an exemplary embodiment of the present specification, Ar1 to Ar6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

According to another exemplary embodiment, the Ar1 to Ar6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent groups bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocycle is formed.

In another exemplary embodiment, Ar1 to Ar6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group containing at least one of O, S and N as a hetero-element having 2 to 30 carbon atoms, or adjacent groups bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms; Or a substituted or unsubstituted hetero element having 2 to 60 carbon atoms to form a heterocycle including at least one of O, S, and N.

According to another exemplary embodiment, the Ar1 to Ar6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted fluorene ring; Substituted or unsubstituted thioxanthene ring; Or to form a substituted or unsubstituted xanthene ring (xanthene).

In another exemplary embodiment, Ar1 to Ar6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a methyl group, or an adjacent group is bonded to a fluorene ring; Thioxanthene ring; Or to form xanthene ring (xanthene). Ar1 and Ar2; Ar3 and Ar4; and Ar5 and Ar6 can be interpreted as adjacent groups.

Ar1 and Ar2; Ar3 and Ar4; And/or Ar5 and Ar6 may each be bonded to each other to form a ring in any one of the following structures, and W may be O or S in the following structures, and the following structures may be further substituted.

In the above structure, W means O or S.

According to an exemplary embodiment of the present specification, Chemical Formula 3 may be represented by the following Chemical Formula 3-1 or 3-2.

[Chemical Formula 3-1]

[Chemical Formula 3-2]

In Formulas 3-1 and 3-2,

R1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R2 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

W1 and W2 are the same as or different from each other, and each independently a single bond, O or S,

Ar11 to Ar14, R7 and R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

m1 and m2 are each an integer of 0 to 8, and when m1 and m2 are each 2 or more, the substituents in parentheses are the same as or different from each other,

n1 and n2 are each an integer of 0 to 6, and when n1 and n2 are each 2 or more, the substituents in parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, W1 and W2 are the same as or different from each other, and each independently a single bond, O or S.

In the exemplary embodiment of the present specification, W1 and W2 are a single bond. When W1 is a single bond, two benzene ring carbon atoms to which W1 is connected in Formula 3-2 are bonded to each other to form a 5-membered ring. When W2 is a single bond, two benzene ring carbon atoms to which W2 is connected in Formula 3-2 are bonded to each other to form a 5-membered ring. When both W1 and W2 are single bonds, Chemical Formula 3-2 has the following core structure.

In the exemplary embodiment of the present specification, W1 and W2 are O.

In the exemplary embodiment of the present specification, W1 and W2 are S.

According to an exemplary embodiment of the present specification, Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

According to another exemplary embodiment, the Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C20 alkyl group.

In another exemplary embodiment, Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; Or a substituted or unsubstituted ethyl group.

According to another exemplary embodiment, the Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Or an ethyl group.

According to an exemplary embodiment of the present invention, Chemical Formula 4 may be represented by the following Chemical Formula 4-1.

[Formula 4-1]

In Formula 4-1,

R1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R2 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

W3 is a single bond, O or S,

R9 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

m3 is an integer from 0 to 8, and when m3 is 2 or more, a plurality of R9s are the same as or different from each other,

n1 and n2 are each an integer of 0 to 6, and when n1 and n2 are each 2 or more, the substituents in parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, W3 is a single bond.

[0366] According to an exemplary embodiment of the present specification, R9 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

According to another exemplary embodiment, R9 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

According to another exemplary embodiment, R9 is hydrogen.

According to an exemplary embodiment of the present specification, m3 is an integer of 0 to 2, and when m3 is 2, two R9s are the same as or different from each other.

In the exemplary embodiment of the present specification, R2 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

According to another exemplary embodiment, the R2 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, R1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

According to another exemplary embodiment, R1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

In another exemplary embodiment, R1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted indolocarbazole group; Or it is a substituted or unsubstituted structure below.

According to another exemplary embodiment, R1 is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heterocyclic group having 2 to 30 carbon atoms, an arylamine group having 6 to 30 carbon atoms, and having 1 to 20 carbon atoms. An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of an alkoxy group and an aryloxy group having 6 to 30 carbon atoms; Or a C1-C20 alkyl group, a C6-C30 aryl group, a C2-C30 heterocyclic group, a C6-C30 arylamine group, a C1-C20 alkoxy group, and a C6-C30 aryloxy group It is a C2-C30 heterocyclic group which is substituted or unsubstituted with one or more selected from the group consisting of.

In another exemplary embodiment, R1 is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heterocyclic group having 2 to 30 carbon atoms, an arylamine group having 6 to 30 carbon atoms, and having 1 to 20 carbon atoms. A phenyl group unsubstituted or substituted with one or more selected from the group consisting of an alkoxy group and an aryloxy group having 6 to 30 carbon atoms; Consisting of a C1-C20 alkyl group, a C6-C30 aryl group, a C2-C30 heterocyclic group, a C6-C30 arylamine group, a C1-C20 alkoxy group, and a C6-C30 aryloxy group A biphenyl group unsubstituted or substituted with one or more selected from the group; Consisting of a C1-C20 alkyl group, a C6-C30 aryl group, a C2-C30 heterocyclic group, a C6-C30 arylamine group, a C1-C20 alkoxy group, and a C6-C30 aryloxy group A naphthyl group unsubstituted or substituted with one or more selected from the group; Consisting of a C1-C20 alkyl group, a C6-C30 aryl group, a C2-C30 heterocyclic group, a C6-C30 arylamine group, a C1-C20 alkoxy group, and a C6-C30 aryloxy group An anthracenyl group unsubstituted or substituted with one or more selected from the group; Consisting of a C1-C20 alkyl group, a C6-C30 aryl group, a C2-C30 heterocyclic group, a C6-C30 arylamine group, a C1-C20 alkoxy group, and a C6-C30 aryloxy group Dibenzofuran group unsubstituted or substituted with one or more selected from the group; Consisting of a C1-C20 alkyl group, a C6-C30 aryl group, a C2-C30 heterocyclic group, a C6-C30 arylamine group, a C1-C20 alkoxy group, and a C6-C30 aryloxy group Carbazole group unsubstituted or substituted with one or more selected from the group; Consisting of a C1-C20 alkyl group, a C6-C30 aryl group, a C2-C30 heterocyclic group, a C6-C30 arylamine group, a C1-C20 alkoxy group, and a C6-C30 aryloxy group An indolocarbazole group unsubstituted or substituted with one or more selected from the group; Or a C1-C20 alkyl group, a C6-C30 aryl group, a C2-C30 heterocyclic group, a C6-C30 arylamine group, a C1-C20 alkoxy group, and a C6-C30 aryloxy group It is the following structure which is unsubstituted or substituted with one or more selected from the group consisting of.

In another exemplary embodiment, R1 is a phenyl group unsubstituted or substituted with at least one selected from the group consisting of a methyl group, a tert-butyl group, a carbazole group, a diphenylamine group, a methoxy group, and a benzyloxy group; Biphenyl group; Naphthyl group; Anthracenyl group substituted with a phenyl group; Dibenzofuran group; A carbazole group substituted with a phenyl group; Indolocarbazole; Or the following structure.

According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; Or, as a substituted or unsubstituted heteroelement having 2 to 30 carbon atoms, it is a heterocyclic group containing at least one of O, S, and N, or is bonded to an adjacent group to form a substituted or unsubstituted ring having 2 to 60 carbon atoms.

According to another exemplary embodiment, R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or combined with an adjacent group to form a substituted or unsubstituted hydrocarbon ring having 2 to 30 carbon atoms.

In another exemplary embodiment, R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; Or a substituted or unsubstituted butyl group, or a plurality of R 2 or a plurality of R 3 bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 2 to 30 carbon atoms.

According to another exemplary embodiment, R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Or a tert-butyl group, or a plurality of R2 or a plurality of R3 are bonded to each other to form benzene.

According to an exemplary embodiment of the present invention, R4 to R6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

According to another exemplary embodiment, R4 to R6 are the same as or different from each other, and each independently an alkyl group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an arylamine group having 6 to 30 carbon atoms, and 6 carbon atoms. A C6-C60 aryl group unsubstituted or substituted with an aryl group having 2 to 30 carbon atoms or a heterocyclic group having 2 to 30 carbon atoms; Or a C1-C20 alkyl group, a C6-C30 aryloxy group, a C6-C30 arylamine group, a C6-C30 aryl group, or a C2-C30 heterocyclic group substituted or unsubstituted with a C2-C30 heterocyclic group It is a heterocyclic group of 60.

According to another exemplary embodiment, R4 to R6 are the same as or different from each other, and each independently an alkyl group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an arylamine group having 6 to 30 carbon atoms, and 6 carbon atoms. A phenyl group unsubstituted or substituted with an aryl group having 2 to 30 carbon atoms or a heterocyclic group having 2 to 30 carbon atoms; A naphthyl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heterocyclic group having 2 to 30 carbon atoms; Dibenzofuran unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heterocyclic group having 2 to 30 carbon atoms group; Thiophene group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heterocyclic group having 2 to 30 carbon atoms ; Or a carbazole group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heterocyclic group having 2 to 30 carbon atoms to be.

According to another exemplary embodiment, the R4 to R6 are the same as or above each other, and each independently a methyl group, a tert-butyl group, a benzyloxy group, a diphenylamine group, or a phenyl group unsubstituted or substituted with a carbazole group; Naphthyl group; Dibenzofuran group; Dibenzothiophene group; Or N-phenylcarbazole group.

According to an exemplary embodiment of the present specification, n1 and n2 are each an integer of 0 to 2, and when n1 and n2 are each 2, the substituents in parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, R7 and R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

According to another exemplary embodiment, R7 and R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

In another exemplary embodiment, R7 and R8 are hydrogen.

According to an exemplary embodiment of the present specification, m1 and m2 are 0 or 1, respectively.

In the exemplary embodiment of the present specification, Formula 1 may be represented by any one of the following structures.

The polycyclic compound of Formula 1 according to an exemplary embodiment of the present invention may have a core structure as shown in the following scheme. Substituents may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

<Scheme 1a>

Intermediate a intermediate b

<Scheme 1b>

Intermediate b

In Reaction Scheme 1a, a cyclic intermediate a substituted with a primary amine and a halogen may be synthesized through a general amination reaction (Bchwald-Hart? amination reaction or Ulman reaction). In Reaction Formula 1a, the equivalent ratio of intermediate a and primary amine should be used in an amount of 2 equivalents or more/1 equivalent, and preferably, 2.0 to 2.5 equivalents of intermediate a should be used. Hal1 and Hal2 may be chlorine, bromine, or iodine. For selective synthesis, Hal1 is preferably chlorine, and Hal2 is preferably bromine or iodine.

Reaction Scheme 1b is a reaction for forming triallylborane. In the case of a compound containing boron, R7 may be a halide, or an alkoxy or allyloxy form may be used. Reaction Scheme 1b shows that before adding the borane compound, first, the intermediate b must be subjected to a litigation, and lithium metal is directly used, or n-butyllithium, tert-butyllithium, sec-butyllithium, lithium diisopropylamide Organolithium reagents such as can be used. In addition, lithium 4,4'-di-tert-butylbiphenyl anion radical or lithium naphthalene ion radical may be used. After the litigation proceeds, a borane compound is added to complete the reaction, so that the core structure of Formula 1 can be prepared.

In addition, by introducing various substituents into the core structure of the above structure, a compound having the inherent characteristics of the introduced substituent can be synthesized. For example, by introducing a substituent mainly used for the hole injection layer material, the hole transport material, the emission layer material, and the electron transport layer material used in the manufacture of an organic light emitting device into the core structure, it is possible to synthesize a material that meets the conditions required by each organic material layer. I can.

In addition, the organic light-emitting device according to 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 at least one of the organic material layers includes the aforementioned polycyclic compound.

The organic light-emitting device of the present invention may be manufactured by a conventional method and material of an organic light-emitting device, except that one or more organic material layers are formed by using the polycyclic compound described above.

The compound 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 coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting 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 a smaller number of organic material layers.

In the organic light-emitting device of the present invention, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the polycyclic compound described above.

In the organic light-emitting device of the present invention, the organic material layer may include a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer may include the aforementioned polycyclic compound.

In another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes the polycyclic compound described above.

According to another exemplary embodiment, the organic material layer may include an emission layer, and the emission layer may include the aforementioned polycyclic compound as a dopant of the emission layer.

In another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes the above-described polycyclic compound as a dopant of the emission layer, and may further include a fluorescent host or a phosphorescent host.

In another exemplary embodiment, the organic material layer includes an emission layer, the emission layer includes the polycyclic compound described above as a dopant of the emission layer, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals, or metal compounds dopants Can be included as.

As another example, the organic material layer includes an emission layer, and the emission layer includes the aforementioned polycyclic compound as a dopant of the emission layer, includes a fluorescent host or a phosphorescent host, and may be used together with an iridium-based (Ir) dopant.

According to another exemplary embodiment, the organic material layer may include an emission layer, the emission layer may include a polycyclic compound represented by Formula 1 as a dopant, and another organic compound as a host. In this case, the dopant may be included in an amount of 0.1 to 49 parts by weight, and preferably 0.5 to 10 parts by weight, based on 100 parts by weight of the host in the light emitting layer.

According to another exemplary embodiment, the organic material layer may include an emission layer, and the emission layer may include the aforementioned polycyclic compound as a host of the emission layer.

As another example, the organic material layer may include an emission layer, and the emission layer may include the polycyclic compound described above as a host of the emission layer, and may include a dopant.

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

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

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 an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In such a structure, the polycyclic compound may be included in the light emitting layer 3.

FIG. 2 illustrates a structure of an organic light emitting diode in which an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, and a cathode 4 are sequentially stacked on a substrate 1. In such a structure, the polycyclic compound may be included in the hole transport layer 5 or the light emitting layer 3.

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, and uses a metal or conductive metal oxide or alloy thereof on a substrate. It can be prepared by depositing an anode to form an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to 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.

The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and the like, but is not limited thereto and may have a single layer structure. In addition, the organic material layer is made of a variety of polymer materials, and is used in a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made in layers.

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); ZnO: Al or SnO _2: a combination of a metal and an oxide such as 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 multi-layered materials such as LiF/Al or LiO ₂ /Al, but are 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 HOMO (highest occupied molecular orbital) 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 hole injection materials include metal porphyrine, 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.

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

The emission layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. As the light-emitting material, a material capable of emitting light in a visible light region by transporting 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-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The host material of the light emitting layer includes a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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

As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable. Specific examples include 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 injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the hole injection layer, In addition, a compound excellent in thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-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 hole blocking layer is a layer that prevents 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 complexes, etc., but are not limited thereto.

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

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

< Synthesis example >

Synthesis example 1. Synthesis of compound 1

1) Synthesis of Intermediate 2

Intermediate 1 Intermediate 2

Intermediate 1 (2 equivalents), aniline (1 equivalent), potassium-tert-butoxide (2.5 equivalents), and palladium acetate (0.06 equivalents) shown in the reaction formula are dissolved in anhydrous toluene, and then tris-tert-butylphosphine (0.15 equivalents) ) Was added. Then, it was stirred and reacted for 24 hours while refluxing under nitrogen. After the reaction was completed, the reaction solution was extracted through methylene chloride and distilled water, and the remaining moisture was removed using magnesium sulfate as the organic phase. Column chromatography purification was performed using methylene chloride/hexane to obtain an intermediate 2 as a yellow powder. (Yield 65%)

Mass spectrometry of Intermediate 2 (FAB, M ⁺ ): 675

¹ H NMR of Intermediate 2: δ 6.28 (s, 2H), 7.00 to 7.23 (m, 8H), 7.35 to 7.51 (m, 11H), 7.63 to 7.70 (m, 6H).

2) Synthesis of compound 1

Intermediate 2 Compound 1

Intermediate 2 (1.0 equivalent) was dissolved in tetrahydrofuran from which moisture was removed under a nitrogen atmosphere, and stirred while lowering to -78 °C. Next, a 1.6 M butyllithium solution (2.2 equivalents) was slowly added at -78 °C, then gradually increased to room temperature and stirred for 2 hours. After the temperature was again lowered to -78 °C, a solution in which dimethoxyphenylborane (1.0 equivalent) was dissolved in anhydrous tetrahydrofuran was slowly added thereto, followed by stirring for 2 hours. The reaction solution was gradually raised to room temperature and then stirred for an additional 6 hours. Finally, water and tetrahydrofuran solution were slowly added to terminate the reaction. After filtering the reaction mixture solution, the filtered solid was washed with methanol and acetone, followed by sublimation purification to obtain pure compound 1. (Yield 41%)

Mass spectrometry of compound 1 (FAB, M ⁺ ): 693

¹ H NMR of Compound 1: δ 6.38 (s, 2H), 7.08 to 7.23 (m, 10H), 7.31 to 7.48 (m, 9H), 7.65 to 7.73 (m, 6H), 7.81 to 7.93 (m, 3H) , 8.02 (d, 2H).

Synthesis example 2. Synthesis of compound 2

1) Synthesis of Intermediate 4

Intermediate 3 Intermediate 4

Intermediate 3 (2 equivalents), aniline (1 equivalent), potassium-tert-butoxide (2.5 equivalents), and palladium acetate (0.06 equivalents) shown in the reaction formula are dissolved in anhydrous toluene, and then tris-tert-butylphosphine (0.15 equivalents) ) Was added. Then, it was stirred and reacted for 24 hours while refluxing under nitrogen. After the reaction was completed, the reaction solution was extracted through ethyl acetate and distilled water, and the remaining moisture was removed using magnesium sulfate as the organic phase. Column chromatography purification was performed using methylene chloride/hexane to obtain an intermediate 4 as a yellow powder. (Yield 55%)

Mass spectrometry of intermediate 4 (FAB, M ⁺ ): 699

¹ H NMR of Intermediate 4: δ 6.44 (s, 2H), 7.03-7.43 (m, 13H), 7.50-7.61 (m, 8H), 7.72 (t, 2H), 7.88 (d, 2H).

2) Synthesis of Intermediate 5

Intermediate 4 Intermediate 5

After dissolving 2-bromo-1,1'-biphenyl (2.1 equivalents) in water-removed tetrahydrofuran under a nitrogen atmosphere, the mixture was stirred while lowering to -78 °C. Next, a 1.6 M butyllithium solution (2.2 equivalents) was slowly added at -78 °C and stirred for 2 hours. After that, a solution in which Intermediate 4 (1.0 equivalent) was dissolved in anhydrous tetrahydrofuran was slowly added and stirred for 2 hours. The reaction solution was gradually raised to room temperature and then stirred for an additional 6 hours. After the reaction was terminated by slowly adding water and tetrahydrofuran solution, the reaction product was extracted using methylene chloride and distilled water, and the organic layer was recovered to remove the solvent. Tetrahydroleuran/acetic acid/hydrochloric acid was added to the obtained solid in a volume ratio of 1/1/0.01, followed by stirring at 60°C for 24 hours. After the reaction mixture solution was extracted with methylene chloride, it was purified by column chromatography using a mixed solvent of ethyl acetate/hexane as a developing solvent. Thereafter, the solvent was removed to obtain Intermediate 5. (Yield 71%)

Mass spectrometry of intermediate 5 ( FAB , M ⁺ ): 971

Of intermediate 5 ^One H NMR: δ 6.31 (s, 2H), 6.95-7.59 (m, 33H), 7.82 (d, 4H), 7.95 (d, 4H).

3) Synthesis of compound 2

Intermediate 5 Compound 2

Intermediate 5 (1.0 equivalent) was dissolved in tetrahydrofuran from which moisture was removed under a nitrogen atmosphere, and stirred while lowering to -78 °C. Next, a 1.6 M butyllithium solution (2.2 equivalents) was slowly added at -78 °C, then gradually increased to room temperature and stirred for 2 hours. After the temperature was again lowered to -78 °C, a solution in which dimethoxyphenylborane (1.0 equivalent) was dissolved in anhydrous tetrahydrofuran was slowly added thereto, followed by stirring for 2 hours. The reaction solution was gradually raised to room temperature and then stirred for an additional 6 hours. Finally, water and tetrahydrofuran solution were slowly added to terminate the reaction. After filtering the reaction mixture solution, the filtered solid was washed with methanol and acetone, followed by sublimation purification to obtain pure compound 2. (Yield 41%)

Mass spectrometry of compound 2 (FAB, M ⁺ ): 989

¹ H NMR of compound 2: δ 6.48 (s, 2H), 7.01 to 7.59 (m, 36H), 7.80 (d, 4H), 7.87 (d, 2H), 7.92 (d, 4H).

Synthesis example 3. Synthesis of compound 3

1) Synthesis of Intermediate 6

Intermediate 1 Intermediate 6

Intermediate 1 (1 equivalent), aniline (1 equivalent), potassium-tert-butoxide (1.3 equivalent), and palladium acetate (0.04 equivalent) were dissolved in anhydrous toluene, and then tris-tert-butylphosphine (0.10 equivalent) was added. Then, it was reacted for 24 hours while refluxing under a nitrogen atmosphere. After the reaction was completed, the reaction solution was extracted through methylene chloride and distilled water, and the remaining moisture was removed using magnesium sulfate as the organic phase. Ethyl acetate/hexane was purified by column chromatography using a developing solvent to obtain an intermediate 6 as a yellow powder. (Yield 53%)

Mass spectrometry of intermediate 6 (FD, M+H ⁺ ): 385.

2) Synthesis of Intermediate 7

Intermediate 6 Intermediate 3 Intermediate 7

As shown in the reaction scheme, intermediate 6 (1 equivalent), intermediate 3 (1 equivalent), potassium-tert-butoxide (1.3 equivalent), and palladium acetate (0.04 equivalent) are dissolved in anhydrous toluene, and then tris-tert-butylphosphine (0.10 eq) was added. Then, it was stirred and reacted for 24 hours while refluxing under nitrogen. After the reaction was completed, the reaction solution was extracted through methylene chloride and distilled water, and the remaining moisture was removed using magnesium sulfate as the organic phase. Purification by column chromatography was performed using methylene chloride/hexane to obtain an intermediate 7 as a yellow powder. (Yield 63%)

Mass spectrometry of intermediate 7 (FAB, M ⁺ ): 687

¹ H NMR of Intermediate 7: δ 6.30 (s, 1H), 6.41 (s, 1H), 7.03 to 7.38 (m, 16H), 7.41 to 7.49 (m, 7H), 7.70 (t, 1H), 7.85 (d , 1H).

3) Synthesis of Intermediate 8

Intermediate 7 Intermediate 8

In a nitrogen atmosphere, 2-bromo-1,1'-biphenyl (1.1 equivalents) was dissolved in water-removed tetrahydrofuran, followed by stirring while lowering to -78 °C. Next, a 1.6 M butyllithium solution (1.1 equivalents) was slowly added at -78°C, followed by stirring for 2 hours. After that, a solution in which Intermediate 7 (1.0 equivalent) was dissolved in anhydrous tetrahydrofuran was slowly added and stirred for 2 hours. The reaction solution was gradually raised to room temperature and then stirred for an additional 6 hours. After the reaction was terminated by slowly adding water and tetrahydrofuran solution, the reaction product was extracted using methylene chloride and distilled water, and the organic layer was recovered to remove the solvent. After adding tetrahydroleuran/acetic acid/hydrochloric acid in a volume ratio of 1/1/0.01 to the obtained solid content, the mixture was stirred at 60° C. for 24 hours. After extracting the reaction mixture solution with methylene chloride, It was purified by column chromatography using a mixed solvent of ethyl acetate/hexane as a developing solvent. Thereafter, the solvent was removed to obtain an intermediate 8. (Yield 75%)

Mass spectrometry of intermediate 8 (FAB, M ⁺ ): 823

¹ H NMR of Intermediate 8: δ 6.23 (s, 1H), 6.39 (s, 1H), 6.98-7.69 (m, 29H), 7.80 (d, 2H), 7.92 (d, 2H).

3) Synthesis of compound 3

Intermediate 8 compound 3

After dissolving Intermediate 8 (1.0 equivalent) in anhydrous tetrahydrofuran under a nitrogen atmosphere, the mixture was stirred while lowering it to -78 °C. Next, a 1.6 M butyllithium solution (2.2 equivalents) was slowly added at -78 °C, then gradually increased to room temperature and stirred for 2 hours. After the temperature was again lowered to -78 °C, a solution in which dimethoxyphenylborane (1.0 equivalent) was dissolved in anhydrous tetrahydrofuran was slowly added thereto, followed by stirring for 2 hours. The reaction solution was gradually raised to room temperature and then stirred for an additional 6 hours. Finally, water and tetrahydrofuran solution were slowly added to terminate the reaction. After filtering the reaction mixture solution, the filtered solid was washed with methanol and acetone, followed by sublimation purification to obtain pure compound 3. (Yield 38%)

Mass spectrometry of compound 3 (FAB, M ⁺ ): 841

¹ H NMR of compound 3: δ 6.20 (s, 1H), 6.35 (s, 1H), 6.91 to 7.55 (m, 32H), 7.82 (d, 2H), 7.90 (d, 2H), 7.96 (d, 2H ).

Synthesis example 4. Synthesis of compound 4

1) Synthesis of compound 4

Intermediate 2 Compound 4

Intermediate 2 (1.0 equivalent) was dissolved in tetrahydrofuran from which moisture was removed under a nitrogen atmosphere, and stirred while lowering to -78 °C. Next, a 1.6 M butyllithium solution (2.2 equivalents) was slowly added at -78 °C, then gradually increased to room temperature and stirred for 2 hours. After lowering the temperature to -78 °C again, a solution in which 4-(dimethoxy)dibenzofuran (1.0 equivalent) was dissolved in anhydrous tetrahydrofuran was slowly added thereto, followed by stirring for 2 hours. The reaction solution was gradually raised to room temperature and then stirred for an additional 6 hours. Finally, water and tetrahydrofuran solution were slowly added to terminate the reaction. After filtering the reaction mixture solution, the filtered solid was washed with methanol and acetone, followed by sublimation purification to obtain pure compound 4. (Yield 33%)

Mass spectrometry of compound 4 (FAB, M ⁺ ): 783

¹ H NMR of Compound 4: 6.40 (s, 2H), 7.05 to 7.45 (m, 19H), 7.65 to 7.73 (m, 3H), 7.80 to 7.75 (m, 6H), 8.02 (d, 1H), 8.07 ( d, 1H), 8.12 (d, 1H), 8.17 (d, 1H).

< Example / Comparative example : Fabrication of organic light emitting device>

Example One.

Device structure: ITO/NPB/ADN: Compound 1/BPhen/LiF/Al

The positive electrode ITO substrate was cleaned with pure water and isopropyl alcohol for 30 minutes under ultrasonic waves. After surface treatment of the cleaned ITO substrate using short-wavelength ultraviolet rays, NPB (4,4′-bis(N-(1-naphthyl)-N-phenylamino)biphenyl), a hole injection or transport material, was added to 1x10 ^-6 torr. A 50 nm hole transport layer was formed by depositing at a rate of 0.1 nm/s under pressure. Thereafter, ^{under a pressure of 1x10 -6} torr, ADN (9,10-di(2-naphthyl)anthracene), a fluorescent host material, was deposited at a rate of 0.1 nm/s, while simultaneously depositing Compound 1, a fluorescent dopant material, at 0.005 nm/s A light emitting layer (30 nm) was formed by co-depositing at a rate of. (Host weight ratio: dopant weight ratio = 100:5) BPhen (4,7-diphenyl-1,10-phenanthroline) as an electron transport material was deposited at a rate of 0.1 nm/s under a pressure of ^{1x10 -6 torr to form an electron transport layer of 30 nm.} was formed. after that, LiF was deposited to a rate of 0.01 nm / s under a pressure of 1x10 ^-6 torr to form a 1nm of the electron injection layer as the electron injecting material. then, the Al under the pressure of 1x10 ^-6 torr 0.5 An organic light-emitting device was formed by depositing at a rate of nm/sec to form a 100 nm cathode After the device was formed, the device was sealed using a moisture absorbent and a glass cover glass.

The organic light-emitting device manufactured in Example 1 has a maximum quantum efficiency of 7.9%, a current efficiency of 9.9 cd/A, a maximum electroluminescence wavelength of 459 nm, and x=0.15 and y=0.16 based on the CIE 1931 color coordinates. Showed characteristics. In addition, as a result of measuring the lifetime, the half-life of the luminance was measured as 3560 hr, showing excellent device lifetime characteristics.

Example 2.

Device structure: ITO/NPB/ADN: Compound 2/BPhen/LiF/Al

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2 was used as the fluorescent dopant material of the emission layer. The organic light-emitting device manufactured in Example 2 has a maximum quantum efficiency of 8.1%, a current efficiency of 9.6 cd/A, and a maximum electroluminescence wavelength of 452 nm and x=0.15, y=0.14 based on the CIE 1931 color coordinates. Showed characteristics. In addition, as ^{a result of measuring the acceleration life at 3000 cd/m 2} , the half life of the luminance was measured as 5650 hr, showing excellent device life characteristics.

Comparative example One.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that BDAVBi (4,4'-Bis[4-(diphenylamino)styryl]biphenyl) was used as the fluorescent dopant material of the emission layer. The organic light emitting device manufactured through Comparative Example 1 has a maximum quantum efficiency of 2.3%, a current efficiency of 3.2 cd/A, a power efficiency of 2.2 lm/W, a maximum electroluminescence wavelength of 468 nm, and x=0.15, y= based on the CIE 1931 color coordinate. It was found to be 0.20, showing a low efficiency characteristic compared to the compounds prepared in the present invention, and the color purity also showed a light-emitting characteristic in a light blue region. In addition, as ^{a result of measuring the acceleration life at 3000 cd/m 2} , the half life of the light emission luminance was measured as 212 hr.

It can be seen that the organic light-emitting devices of Examples 1 and 2 using the polycyclic compound represented by Chemical Formula 1 of the present application not only exhibit better fluorescence emission characteristics than the organic light-emitting device of Comparative Example 1, but also have high efficiency and long life characteristics.

Through the above, although the preferred embodiments of the present specification have been described, the present invention is not limited thereto, and it is possible to implement various modifications within the scope of the claims and the detailed description of the invention, and this also falls within the scope of the invention. Belongs.

1: substrate
2: anode
3: light-emitting layer
4: cathode
5: hole transport layer
6: electron transport layer

Claims (11)

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

In Formula 1,
R1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
X1 and X2 are the same as or different from each other, and each independently O, S, C (=O) or CRbRc,
Rb, Rc, and R2 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,
n1 and n2 are each an integer of 0 to 6, and when n1 and n2 are each 2 or more, the substituents in parentheses are the same as or different from each other,
The "substituted or unsubstituted" is an alkyl group; Alkoxy group; Aryloxy group; Arylamine group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or does not have any substituents. The method according to claim 1,
Formula 1 is a polycyclic compound represented by any one of the following Formulas 2 to 4:
[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,
The definitions of R1 to R6, n1 and n2 are as defined in Formula 1,
X3 to X5 are the same as or different from each other, and each independently O, S or C (=O),
Ar1 to Ar6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,
The "substituted or unsubstituted" is an alkyl group; Alkoxy group; Aryloxy group; Arylamine group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or does not have any substituents. The method according to claim 2,
Formula 3 is a polycyclic compound represented by the following Formula 3-1 or 3-2:
[Chemical Formula 3-1]

[Chemical Formula 3-2]

In Formulas 3-1 and 3-2,
R1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R2 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
W1 and W2 are the same as or different from each other, and each independently a single bond, O or S,
Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R7 and R8 are the same as or different from each other, and each independently an alkyl group; Alkoxy group; Aryloxy group; Arylamine group; Aryl group; Or a heterocyclic group,
m1 and m2 are each an integer of 0 to 8, and when m1 and m2 are each 2 or more, the substituents in parentheses are the same as or different from each other,
n1 and n2 are each an integer of 0 to 6, and when n1 and n2 are each 2 or more, the substituents in parentheses are the same as or different from each other,
The "substituted or unsubstituted" is an alkyl group; Alkoxy group; Aryloxy group; Arylamine group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or does not have any substituents. The method according to claim 2,
Formula 4 is a polycyclic compound represented by the following Formula 4-1:
[Formula 4-1]

In Formula 4-1,
R1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R2 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
W3 is a single bond, O or S,
R9 is an alkyl group; Alkoxy group; Aryloxy group; Arylamine group; Aryl group; Or a heterocyclic group,
m3 is an integer from 0 to 8, and when m3 is 2 or more, a plurality of R9s are the same as or different from each other,
n1 and n2 are each an integer of 0 to 6, and when n1 and n2 are each 2 or more, the substituents in parentheses are the same as or different from each other,
The "substituted or unsubstituted" is an alkyl group; Alkoxy group; Aryloxy group; Arylamine group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or does not have any substituents. The method according to claim 1,
R1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group,
The "substituted or unsubstituted" is an alkyl group; Alkoxy group; Aryloxy group; Arylamine group; Aryl group; And a polycyclic compound that is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or does not have any substituents. A polycyclic compound represented by any one of the following structures:

. 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 comprises the polycyclic compound according to any one of claims 1 to 6 Organic light emitting device. The method of claim 7,
The organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the polycyclic compound. The method of claim 7,
The organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the polycyclic compound. The method of claim 7,
The organic material layer includes an emission layer, and the emission layer includes the polycyclic compound. The method of claim 7,
The organic material layer includes an emission layer, and the organic light emitting device includes the polycyclic compound as a dopant of the emission layer.

Images