KR20190051869A - Multicyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a polycyclic compound, capable of improving lifetime characteristics in an organic light emitting device, and to an organic light emitting device including the same. The polycyclic compound of the present invention is represented by chemical formula 1. In chemical formula 1, X1 and X2 are the same or different, and are each independently O, S, or CRaRb, and L1 and L2 are the same or different, and are each independently a direct bond, or a substituted or unsubstituted arylene group.

Description

TECHNICAL FIELD [0001] The present invention relates to a polycyclic compound and an organic light-

This application claims the benefit of Korean Patent Application No. 10-2017-0146806, filed on November 6, 2017, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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

In the present specification, an organic light emitting element is a light emitting element using an organic semiconductor material, and requires the exchange of holes and / or electrons between the electrode and the organic semiconductor material. The organic light emitting device can be roughly classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Emitting device. The second type is a light emitting device that injects holes and / or electrons into an organic semiconductor material layer that interfaces with the electrode by applying a voltage or current to two or more electrodes, and operates by injected electrons and holes.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The luminescent material has blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color.

Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with a light emitting layer in a small amount, the excitons generated in the host are transported as a dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, light of a desired wavelength can be obtained depending on the type of the dopant used.

In order to sufficiently exhibit the excellent characteristics of the organic light emitting device described above, materials constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material and an electron injecting material are supported by stable and efficient materials Development of new materials is continuously required.

Korean Patent Laid-Open No. 10-2011-099239

In this specification, compounds and organic light emitting devices containing them are described.

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

[Chemical Formula 1]

In Formula 1,

X1 and X2 are the same or different and each independently O, S or CRaRb,

Ra, Rb and R1 to R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 and L2 are the same or different from each other and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

RA1 to RA4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl 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 heterocycle,

A1 and A2 are the same or different and each independently represents a monocyclic or polycyclic substituted or unsubstituted ring,

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

m1 and m2 are each 0 or 1, and m1 + m2 is 1 or more.

According to an embodiment of the present invention, there is also provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by Formula 1 do.

The compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can improve the life characteristics in the organic light emitting device and / or the organic light emitting device. In particular, the compounds described in this specification can be used as a material for a hole injection layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer.

Fig. 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 element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

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

The present invention provides a compound represented by the following formula (1). When the compound represented by the following formula (1) is used for the organic material layer of the organic light emitting device, not only the efficiency of the organic light emitting device is always maintained, but also the lifetime characteristics are excellent.

In addition, according to one embodiment of the present invention, the compound represented by the following general formula (1) has a structure in which at least one amine group is substituted in the core structure and can be used as a dopant of a light emitting layer of an organic light emitting device, It is possible not only to improve the efficiency and lifetime characteristics of the device, but also to obtain an element having excellent color recall.

[Chemical Formula 1]

In Formula 1,

X1 and X2 are the same or different and each independently O, S or CRaRb,

Ra, Rb and R1 to R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 and L2 are the same or different from each other and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

RA1 to RA4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl 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 heterocycle,

A1 and A2 are the same or different and each independently represents a monocyclic or polycyclic substituted or unsubstituted ring,

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

m1 and m2 are each 0 or 1, and m1 + m2 is 1 or more.

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

In this specification, when a member is located on another member, it 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 substituents herein are described below, but are not limited thereto.

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

As used herein, the term " substituted or unsubstituted " A halogen group; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, " a substituent to which at least two substituents are connected " may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

Illustrative examples of such substituents are set forth below, but are not limited thereto.

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

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 one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert- And a til group, but are not limited thereto.

In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples thereof include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

In this specification, the amine group is -NH ₂ ; An alkylamine group; Arylalkylamine groups; An arylamine group; An arylheteroarylamine group; 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 of the alkylamine group is not particularly limited, but may be 1 to 40, and may be 1 to 20 according to one embodiment. 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 containing two or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, Group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a biphenylphenylamine group, a divinylamine group, and a fluorenylphenylamine group.

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 containing two or more heteroaryl groups may simultaneously contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.

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

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

As used herein, an alkylheteroarylamine group refers to an amine group substituted with an alkyl group and a heteroaryl group.

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

In the present specification, a 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,

,

, A spirofluorenyl group

(9,9-dimethylfluorenyl group), and

(9,9-diphenylfluorenyl group), and the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heteroaromatic ring group containing at least one of N, O, P, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophenyl, carbazole, imidazole, pyrazole, However, the present invention is not limited thereto.

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

In this specification, " adjacent " The group may mean a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom of the substituent. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as " adjacent " groups to each other.

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

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

In the present specification, the explanation about the aryl group except for the monovalent aromatic hydrocarbon ring can be applied.

In the present specification, the hetero ring includes one or more non-carbon atoms and hetero atoms. Specifically, the hetero atom includes at least one atom selected from the group consisting of N, O, P, S, Si and Se can do. The heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples of the heteroaryl group may be selected except that the aromatic heterocyclic ring is not monovalent.

According to one embodiment of the present disclosure, R5 and R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In another embodiment, R5 and R6 are the same or different and are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to another embodiment, R5 and R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In another embodiment, R5 and R6 are the same or different and are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to one embodiment of the present disclosure, R5 and R6 are each hydrogen.

According to one embodiment of the present disclosure, n1 and n2 are each 0 or 1.

In one embodiment of the present invention, the formula (1) is represented by any one of the following formulas (2) to (4).

(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,

X1 and X2 and R1 to R6, n1, n2, L1, L2, RA1 to RA4, m1 and m2 are as defined in formula (1)

Any one of W1 and W2 is a direct bond and the remainder is O, S or CRR '

W3 and W4 is a direct bond and the remainder is O, S or CR " R "

R, R ', R ", R "' and R 7 to R 12 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

n11 to n16 are each an integer of 0 to 4, and when n11 to n16 are each 2, the substituents in the parentheses of 2 or more are the same or different from each other.

According to one embodiment of the present disclosure, X1 and X2 are the same or different from each other, and each independently O, S or CRaRb.

According to yet another embodiment, X1 and X2 are O.

According to another embodiment, X1 and X2 are S.

According to another embodiment, X1 and X2 are CRaRb.

In another embodiment, X1 is O and X2 is S.

In another embodiment, X1 is O and X2 is CRaRb.

In another embodiment, X1 is S and X2 is O.

In another embodiment, X1 is S and X2 is CRaRb.

In another embodiment, X1 is CRaRb and X2 is O.

In another embodiment, X1 is CRaRb and X2 is S.

According to one embodiment of the present invention, Ra and Rb are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to another embodiment, Ra and Rb are the same or different from each other and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, Ra and Rb are the same or different and each independently hydrogen; 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 one embodiment of the present invention, Ra and Rb are the same or different and each independently represents a substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted pentyl group; A substituted or unsubstituted hexyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

According to another embodiment, Ra and Rb are the same or different and are each independently a methyl group; An ethyl group; Propyl group; Butyl group; Pentyl group; Hexyl group; A phenyl group; A biphenyl group; Or a naphthyl group.

In another embodiment, each Ra and Rb is a methyl group.

According to one embodiment of the present invention, R1 to R4 are the same or different from each other, and each independently hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to another embodiment, R 1 to R 4 are the same or different and each independently hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, R 1 to R 4 are the same or different and each independently hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, R 1 to R 4 are the same or different and each independently hydrogen; A halogen group; Cyano; Methyl group; An ethyl group; Propyl group; Butyl group; Pentyl group; Hexyl group; A phenyl group; A biphenyl group; A terphenyl group; Or a naphthyl group.

According to one embodiment of the present disclosure, each of R1 to R4 is hydrogen.

According to one embodiment of the present invention, A1 and A2 are the same or different and each independently represents a monocyclic or polycyclic substituted or unsubstituted hydrocarbon ring; Or a monocyclic or polycyclic substituted or unsubstituted heterocycle.

According to another embodiment, A1 and A2 are the same or different and each independently represents a monocyclic or polycyclic substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms; Or a monocyclic or polycyclic substituted or unsubstituted C2-C60 heterocycle.

In another embodiment, A1 and A2 are the same or different and each independently represents a monocyclic or polycyclic substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms; Or a monocyclic or polycyclic substituted or unsubstituted C2-C30 heterocycle.

According to another embodiment, A1 and A2 are substituted or unsubstituted benzene rings; A substituted or unsubstituted naphthalene ring; A substituted or unsubstituted benzofuran ring; A substituted or unsubstituted benzothiophene ring; Or a substituted or unsubstituted indene ring.

In another embodiment, A1 and A2 are benzene rings; Naphthalene ring; Benzofuran ring; Benzothiophene ring; Or an indene ring substituted with an alkyl group.

According to another embodiment, A1 and A2 are benzene rings; Naphthalene ring; Benzofuran ring; Benzothiophene ring; Or an indene ring substituted with a methyl group.

According to one embodiment of the present disclosure, any one of W1 and W2 is a direct bond and the remainder is O, S or CRR '.

According to yet another embodiment, W 1 is a direct bond and W 2 is O.

According to yet another embodiment, W1 is a direct bond and W2 is S.

According to yet another embodiment, W1 is a direct bond and W2 is CRR '.

According to yet another embodiment, W2 is a direct bond and W1 is O.

According to yet another embodiment, W2 is a direct bond and W1 is S.

According to yet another embodiment, W2 is a direct bond and W1 is CRR '.

According to one embodiment of the present disclosure, either W3 or W4 is a direct bond and the remainder is O, S or CR " R ".

According to another embodiment, W3 is a direct bond and W4 is O.

According to yet another embodiment, W3 is a direct bond and W4 is S.

According to another embodiment, W3 is a direct bond and W4 is CR " R ".

According to another embodiment, W 4 is a direct bond and W 3 is O.

According to yet another embodiment, W4 is a direct bond and W3 is S.

According to another embodiment, W4 is a direct bond and W3 is CR " R ".

According to one embodiment of the present disclosure, R, R ', R "and R' '' are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to another embodiment, R, R ', R "and R' '' are the same or different from each other and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, R, R ', R "and R' '' are the same or different and each independently hydrogen; 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 another embodiment, R, R ', R "and R' '' are substituted or unsubstituted alkyl groups.

According to another embodiment, R, R ', R "and R' '' are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms.

According to one embodiment of the present invention, R, R ', R' 'and R' '' represent a substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted pentyl group; Or a substituted or unsubstituted hexyl group.

According to another embodiment, R, R ', R " and R "' are methyl groups; An ethyl group; Propyl group; Butyl group; Pentyl group; Or a hexyl group.

According to one embodiment of the present invention, R7 to R12 are the same or different from each other, and each independently hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to another embodiment, R7 to R12 are the same or different from each other and each independently hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, R7 to R12 are the same or different from each other, and each independently hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, R7 to R12 are the same or different from each other, and each independently hydrogen; A halogen group; Cyano; Methyl group; An ethyl group; Propyl group; Butyl group; Pentyl group; Hexyl group; A phenyl group; A biphenyl group; A terphenyl group; Or a naphthyl group.

According to one embodiment of the present disclosure, each of R7 to R12 is hydrogen.

In one embodiment of the present specification, n11 to n16 are each 0 or 1.

According to one embodiment of the present invention, the formula (1) is represented by any one of the following formulas (5) to (7).

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In Formulas 5 to 7,

X1, X2 and R1 to R6, L1, L2 and RA1 to RA4 have the same definitions as in formula (1)

Any one of W1 and W2 is a direct bond and the remainder is O, S or CRR '

W3 and W4 is a direct bond and the remainder is O, S or CR " R "

R, R ', R ", R "' and R 7 to R 12 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

n21 and n22 are each 0 or 1,

each of n23 to n26 is an integer of 0 to 4, and when n23 to n26 are each 2 or more, the substituents in the parentheses of 2 or more are the same or different,

n27 and n28 are each an integer of 0 to 3, and when n27 and n28 are each 2 or more, the substituents in the parentheses of 2 or more are the same or different from each other.

According to one embodiment of the present invention, W1, W2, W3, W4 and R7 to R12 in the above formulas 5 to 7 are as defined above.

According to one embodiment of the present invention, n23 to n29 are each 0 or 1.

In one embodiment of the present invention, L 1 and L 2 are the same or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

According to yet another embodiment, L1 and L2 are the same or different and are each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In another embodiment, L1 and L2 are each a direct bond.

According to one embodiment of the present disclosure, m1 and m2 are each 0 or 1, and m1 + m2 is 1 or 2.

According to one embodiment of the present invention, RA1 to RA4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2-C60 heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted C2-C60 heterocycle.

According to one embodiment of the present invention, RA1 to RA4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C30 heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted C2-C30 heterocycle.

In another embodiment, RA1 to RA4 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2-C30 heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted C2-C30 heterocycle.

According to another embodiment, RA1 to RA4 are the same or different from each other and each independently selected from the group consisting of deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 30 carbon atoms, and an alkyl group having 1 to 20 carbon atoms A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 30 carbon atoms, and an alkyl group having 1 to 20 carbon atoms, Groups are bonded to each other to form a substituted or unsubstituted C2-C30 heterocycle with an alkyl group having 1 to 20 carbon atoms.

In another embodiment, RA1 to RA4 are the same or different from each other and each independently represents one or more groups selected from the group consisting of deuterium, halogen, cyano, trimethylsilyl, methyl, ethyl, An aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with a substituent; Or a heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of a halogen, a cyano group, a trimethylsilyl group, a methyl group, an ethyl group, a propyl group and a butyl group, Is a heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of a methyl group, an ethyl group, a propyl group and a butyl group.

According to another embodiment, the RA1 to RA4 are the same or different and each independently represents one or more groups selected from the group consisting of deuterium, a halogen group, a cyano group, a trimethylsilyl group, a methyl group, an ethyl group, a propyl group, A phenyl group substituted or unsubstituted with a substituent; A biphenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, cyano, trimethylsilyl, methyl, ethyl, propyl and butyl; A naphthyl group substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, a trimethylsilyl group, a methyl group, an ethyl group, a propyl group and a butyl group; A naphthylphenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, a trimethylsilyl group, a methyl group, an ethyl group, a propyl group and a butyl group; A fluorenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, cyano, trimethylsilyl, methyl, ethyl, propyl and butyl; A dibenzofuranyl group substituted or unsubstituted with at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, cyano, trimethylsilyl, methyl, ethyl, propyl and butyl; Or a dibenzothiophenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a halogen, a cyano group, a trimethylsilyl group, a methyl group, an ethyl group, a propyl group and a butyl group, or the adjacent groups may be bonded to each other to form a methyl group, A carbazole group substituted or unsubstituted with at least one substituent selected from the group consisting of a methyl group, a propyl group and a butyl group.

In one embodiment of the present invention, the formula (1) may be represented by any one of the following structures.

       Compound 1 Compound 2 Compound 3

      Compound 4 Compound 5 Compound 6

       Compound 7 Compound 8 Compound 9

      Compound 10 Compound 11 Compound 12

      Compound 13 Compound 14 Compound 15

      Compound 16 Compound 17 Compound 18

       Compound 19 Compound 20 Compound 21

       Compound 22 Compound 23 Compound 24

       Compound 25 Compound 26 Compound 27

Compound 28 Compound 29 Compound 30

       Compound 31 Compound 32 Compound 33

       Compound 34 Compound 35 Compound 36.

The compound represented by the general formula (1) according to one embodiment of the present specification can be produced by the following production method. The substituent may be bonded by a reaction material, a reaction solution, a manufacturing method, or the like known in the art, and the kind, position or number of the substituent may be changed according to a technique known in the art.

The conjugation length of the compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.

In the present invention, compounds having various energy bandgaps can be synthesized by introducing various substituents into the core structure as described above. Further, in the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents to the core structure having the above structure.

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent mainly used in a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic light emitting device into the core structure, a material meeting the requirements of each organic layer is synthesized .

Further, the organic light emitting device according to the present invention includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by Formula 1.

According to one embodiment of the present invention, the organic material layer includes a light emitting layer, and at least one of the organic material layers includes a compound represented by the above-mentioned formula (1), and the light emitting layer may include a compound represented by the following formula .

≪ EMI ID =

In the above formula (1A)

L103 to L106 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar5 to Ar8 are the same or different and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R24 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

p is an integer of 0 to 6,

When p is 2 or more, the substituents in the parentheses are the same or different.

In one embodiment of the present invention, L103 to L106 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

In one embodiment of the present invention, L103 to L106 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

According to another embodiment, L103 to L106 are the same or different and are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophenylene group; A substituted or unsubstituted furanyl group; A substituted or unsubstituted dibenzothiophenylene group; A substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted carbazolylene group.

In another embodiment, L103 to L106 are the same or different and are each independently a direct bond; A phenylene group; Biphenyllylene groups; A terphenylene group; Naphthylene group; Anthracenylene group; Phenanthrenylene group; Triphenylene group; A fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group; Thiophenylene group; A furanylene group; Dibenzothiophenylene groups; Dibenzofuranyl group; Or a carbazolylene group substituted or unsubstituted with an ethyl group or a phenyl group.

According to another embodiment, L103 to L106 are the same or different and are each independently a direct bond; Or one of the following structures.

According to one embodiment of the present disclosure, L103 is a direct bond.

According to one embodiment of the present disclosure, L104 is a phenylene group.

According to one embodiment of the present disclosure, L105 and L106 are direct bonds.

In one embodiment of this disclosure, R24 is selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of this disclosure, R24 is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of this disclosure, R24 is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

In one embodiment of this disclosure, R24 is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C25 heterocyclic group.

In another embodiment, R24 is hydrogen.

According to one embodiment of the present disclosure, p is 0 or 1.

In one embodiment of the present specification, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another embodiment, Ar5 to Ar8 may be the same or different from each other, and each independently hydrogen; An aryl group having 6 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with a heteroaryl group having 2 to 60 carbon atoms; Or a heteroaryl group having 2 to 60 carbon atoms, which is substituted or unsubstituted with an aryl group having 60 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms.

In another embodiment, Ar5 to Ar8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted indolcarbazole group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted isoquinolyl group; A substituted or unsubstituted quinolyl group; A substituted or unsubstituted quinazolyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; A substituted or unsubstituted xanthene group; Or a substituted or unsubstituted dibenzosilyl group.

According to another embodiment, Ar5 to Ar8 are the same or different from each other, and each independently hydrogen; A phenyl group; A biphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; Phenanthrene; Anthracene group; Triphenylene group; A dibenzofurane group substituted or unsubstituted with an aryl group; A naphthobenzofuran group; A dibenzothiophene group substituted or unsubstituted with an aryl group; A carbazole group substituted or unsubstituted with an alkyl group or an aryl group; An alkyl group, or a fluorene group substituted or unsubstituted with an aryl group; A thiophene group substituted or unsubstituted with an aryl group; A furan group substituted or unsubstituted with an aryl group; Benzothiophene group; Benzofuran group; A benzocarbazole group substituted or unsubstituted with an alkyl group or an aryl group; A benzofluorene group substituted or unsubstituted with an alkyl group or an aryl group; Indolecarbazole group; A pyridyl group; An isoquinolyl group substituted or unsubstituted with an aryl group; Quinolyl group; A quinazolyl group substituted or unsubstituted with an aryl group; A triazine group substituted or unsubstituted with an aryl group; A benzimidazole group substituted or unsubstituted with an aryl group; A benzoxazole group substituted or unsubstituted with an aryl group; A benzothiazole group substituted or unsubstituted with an aryl group; An alkyl group, or a dihydroacridine group substituted or unsubstituted with an aryl group; A xanthene group substituted or unsubstituted with an alkyl group or an aryl group; Or a dibenzosilyl group substituted or unsubstituted with an alkyl group or an aryl group.

In another embodiment, Ar5 to Ar8 are the same or different from each other, and each independently hydrogen; A phenyl group; A biphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; Phenanthrene; Anthracene group; Triphenylene group; A dibenzofurane group substituted or unsubstituted with a phenyl group; A naphthobenzofuran group; A dibenzothiophene group substituted or unsubstituted with a phenyl group; A carbazole group substituted or unsubstituted with a methyl group, an ethyl group, or a phenyl group; A methyl group, or a fluorene group substituted or unsubstituted with a phenyl group; A thiophene group substituted or unsubstituted with a phenyl group; A furan group substituted or unsubstituted with a phenyl group; Benzothiophene group; Benzofuran group; A methyl group, or a benzocarbazole group substituted or unsubstituted with a phenyl group; A methyl group, or a benzofluorene group substituted or unsubstituted with a phenyl group; Indolecarbazole group; A pyridyl group substituted or unsubstituted with a phenyl group or a naphthyl group; An isoquinolyl group substituted or unsubstituted with a phenyl group; Quinolyl group; A quinazolyl group substituted or unsubstituted with a phenyl group; A triazine group substituted or unsubstituted with a phenyl group; A benzimidazole group substituted or unsubstituted with a phenyl group; A benzoxazole group substituted or unsubstituted with a phenyl group; A benzothiazole group substituted or unsubstituted with a phenyl group; A methyl group, or a dihydroacridine group substituted or unsubstituted with a phenyl group; A methyl group, or a xanthylene group substituted or unsubstituted with a phenyl group; Or a dibenzosilyl group substituted or unsubstituted with a methyl group or a phenyl group.

In one embodiment of the present specification, Ar5 to Ar8 are the same or different from each other and each independently hydrogen; Or one of the following structures.

According to one embodiment of the present invention, the organic material layer includes a light emitting layer, and at least one of the organic material layers includes a compound represented by Formula 1, and the light emitting layer may include a compound represented by Formula 1B .

The host material of the light emitting layer in the organic material layer of the organic light emitting device of the present specification may include a structure of the following formula (1B).

≪ RTI ID = 0.0 &

In the above formula (1B)

L107 to L109 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar9 to Ar11 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R25 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

q is an integer of 0 to 7,

When q is 2 or more, the substituents in the parentheses are the same or different from each other.

In one embodiment of the present disclosure, R25 is hydrogen; heavy hydrogen; A halogen group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present disclosure, R25 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present disclosure, R25 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

In one embodiment of the present disclosure, R25 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C25 heterocyclic group.

In another embodiment, R25 is hydrogen.

According to one embodiment of the present disclosure, q is 0 or 1.

In one embodiment of the present invention, L107 to L109 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

In one embodiment of the present invention, L107 to L109 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

According to another embodiment, L107 to L109 are the same or different and are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophenylene group; A substituted or unsubstituted furanyl group; A substituted or unsubstituted dibenzothiophenylene group; A substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted carbazolylene group.

In another embodiment, L107 to L109 are the same or different and are each independently a direct bond; A phenylene group; Biphenyllylene groups; A terphenylene group; Naphthylene group; Anthracenylene group; Phenanthrenylene group; Triphenylene group; A fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group; Thiophenylene group; A furanylene group; Dibenzothiophenylene groups; Dibenzofuranyl group; Or a carbazolylene group substituted or unsubstituted with an ethyl group or a phenyl group.

According to another embodiment, L107 to L109 are the same or different and are each independently a direct bond; Or one of the following structures.

In one embodiment of the present specification, L107 to L109 are direct bonds.

In one embodiment of the present specification, Ar9 to Ar11 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another embodiment, Ar9 to Ar11 are the same or different and each independently represents an aryl group having 6 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with a heteroaryl group having 2 to 60 carbon atoms group; Or a heteroaryl group having 2 to 60 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms.

In another embodiment, Ar9 to Ar11 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted indolcarbazole group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted isoquinolyl group; A substituted or unsubstituted quinolyl group; A substituted or unsubstituted quinazolyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; A substituted or unsubstituted xanthene group; Or a substituted or unsubstituted dibenzosilyl group.

According to another embodiment, Ar9 to Ar11 are the same or different from each other, and each independently represents a phenyl group; A biphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; Phenanthrene; Anthracene group; Triphenylene group; A dibenzofurane group substituted or unsubstituted with an aryl group; A naphthobenzofuran group; A dibenzothiophene group substituted or unsubstituted with an aryl group; A carbazole group substituted or unsubstituted with an alkyl group or an aryl group; An alkyl group, or a fluorene group substituted or unsubstituted with an aryl group; A thiophene group substituted or unsubstituted with an aryl group; A furan group substituted or unsubstituted with an aryl group; Benzothiophene group; Benzofuran group; A benzocarbazole group substituted or unsubstituted with an alkyl group or an aryl group; A benzofluorene group substituted or unsubstituted with an alkyl group or an aryl group; Indolecarbazole group; A pyridyl group; An isoquinolyl group substituted or unsubstituted with an aryl group; Quinolyl group; A quinazolyl group substituted or unsubstituted with an aryl group; A triazine group substituted or unsubstituted with an aryl group; A benzimidazole group substituted or unsubstituted with an aryl group; A benzoxazole group substituted or unsubstituted with an aryl group; A benzothiazole group substituted or unsubstituted with an aryl group; An alkyl group, or a dihydroacridine group substituted or unsubstituted with an aryl group; A xanthene group substituted or unsubstituted with an alkyl group or an aryl group; Or a dibenzosilyl group substituted or unsubstituted with an alkyl group or an aryl group.

In another embodiment, Ar9 to Ar11 are the same or different from each other, and each independently represents a phenyl group; A biphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; Phenanthrene; Anthracene group; Triphenylene group; A dibenzofurane group substituted or unsubstituted with a phenyl group; A naphthobenzofuran group; A dibenzothiophene group substituted or unsubstituted with a phenyl group; A carbazole group substituted or unsubstituted with a methyl group, an ethyl group, or a phenyl group; A methyl group, or a fluorene group substituted or unsubstituted with a phenyl group; A thiophene group substituted or unsubstituted with a phenyl group; A furan group substituted or unsubstituted with a phenyl group; Benzothiophene group; Benzofuran group; A methyl group, or a benzocarbazole group substituted or unsubstituted with a phenyl group; A methyl group, or a benzofluorene group substituted or unsubstituted with a phenyl group; Indolecarbazole group; A pyridyl group substituted or unsubstituted with a phenyl group or a naphthyl group; An isoquinolyl group substituted or unsubstituted with a phenyl group; Quinolyl group; A quinazolyl group substituted or unsubstituted with a phenyl group; A triazine group substituted or unsubstituted with a phenyl group; A benzimidazole group substituted or unsubstituted with a phenyl group; A benzoxazole group substituted or unsubstituted with a phenyl group; A benzothiazole group substituted or unsubstituted with a phenyl group; A methyl group, or a dihydroacridine group substituted or unsubstituted with a phenyl group; A methyl group, or a xanthylene group substituted or unsubstituted with a phenyl group; Or a dibenzosilyl group substituted or unsubstituted with a methyl group or a phenyl group.

In one embodiment of the present invention, Ar9 to Ar11 may be the same or different from each other, and each independently selected from the following structures.

.

.

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

The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, 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 injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic 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 a compound represented by the above formula (1).

In the organic light emitting device of the present invention, the organic material layer may include a hole injecting layer or a hole transporting layer, and the hole injecting layer or the hole transporting layer may include the compound represented by the above formula (1).

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the general formula (1).

According to another embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer may include the compound represented by Formula 1 as a dopant in the light emitting layer.

In another embodiment, the organic layer includes a light-emitting layer, wherein the light-emitting layer contains a compound represented by the general formula (1) as a dopant of the light-emitting layer and includes a fluorescent host or a phosphorescent host, As a dopant.

As another example, the organic layer may include a light emitting layer, and the light emitting layer may include a compound represented by Formula 1 as a dopant of the light emitting layer, and may include a fluorescent host or a phosphorescent host, and may be used together with an iridium (Ir) have.

According to another embodiment, the organic layer may include a light emitting layer, and the light emitting layer may include a compound represented by Formula 1 as a host of the light emitting layer.

As another example, the organic layer may include a light emitting layer, and the light emitting layer may include a compound represented by Formula 1 as a host of the light emitting layer, and may include a dopant.

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

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

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

1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated on a substrate 1. In FIG. In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic light emitting device in which an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 are sequentially laminated on a substrate 1 Structure is illustrated. In such a structure, the compound may be included in the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 7, or the electron transporting layer 8.

For example, the organic light emitting device according to the present invention may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate, To form an anode, an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and a material which can be used as a cathode is deposited thereon. In addition to such a method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. The organic material layer may be formed using a variety of polymeric materials by a method such as a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Layer.

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

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

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

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

The light emitting layer may emit red, green or blue light, and may be formed of a phosphor or a fluorescent material. The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

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

Examples of the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

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

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

The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injection layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

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

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

< Synthetic example >

Synthetic example  1. Compound 1>  synthesis

Intermediate 1-1 was synthesized according to Reaction Scheme 1 below.

<Reaction Scheme 1>

                                                      <Intermediate 1-1>

(3,6-dimethoxynaphthalene-2,7-diyl) diboronic acid (28 g, 0.101 mol) and 4-bromo-1-chloro- 4-dioxane [b, d] furan] (69.9 g, 0.233 mol) was dissolved in 1,4-dioxane After dissolving in 250 mL, K ₂ CO ₃ (42.1 g, 0.305 mol) and 120 mL of H ₂ O solution are added. Tetrakis (triphenylphosphine) palladium (0) (6.3 g, 5.48 mmol) was added thereto, and the mixture was heated at reflux for 5 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate (EtOAc) and water. The organic layer was dried over MgSO ₄ , concentrated by filtration, and then purified by column chromatography (n-hexane: EtOAc). As a result, 43.0 g (Yield 68%) of Intermediate 1-1 was obtained. MS: [M + H] &lt; + &gt; = 625

Intermediate 1-2 was synthesized according to Reaction Scheme 2 below.

<Reaction Scheme 2>

    &Lt; Intermediate 1-1 > < Intermediate 1-2 >

Intermediate 1-1 (7.0 g, 1.0 mmol) was dissolved in dichloromethane (100 mL) and then cooled to -40 ° C. BBr ₃ solution (0.5mmol) was added dropwise slowly to a slowly after drying and then the temperature was raised to room temperature and stirred for 8 hours at room temperature and the organic layer obtained by extraction with water and ethyl acetate [EtOAc] with MgSO ₄ filtered, concentrated and then purified by column chromatography (n-Hexane: EtOAc). As a result, 6.0 g (Yield 89.6%) of intermediate 1-2 was obtained. MS: [M + H] &lt; + &gt; = 597

Intermediate 1-3 was synthesized according to Reaction Scheme 3 below.

<Reaction Scheme 3>

     <Intermediate 1-2> <Intermediate 1-3>

The intermediate 1-2 (3 g, 0.5 mmol) was dissolved in dimethylacetamide [DMAc] solution, K ₂ CO ₃ (2.8 g, ₂ mmol) was added and the mixture was refluxed and stirred for 2 hours. After cooling to room temperature, Column chromatography (n-hexane: EtOAc) was used to obtain 2.5 g (Yield 89.3%) of intermediate 1-3. MS: [M + H] &lt; + &gt; = 557

Compound 1 was synthesized according to Reaction Scheme 4 below.

<Reaction Scheme 4>

   <Intermediate 1-3> <Compound 1>

To a solution of N- (4- (tert-butyl) phenyl) -9,9-dimethyl-9H-fluorene-2-amine [N- (4- (12.0 g, 21.5 mmol), bis (tri (tert-butyl) phenyl) -9,9-dimethyl-9H-fluoren-2-amine] (16.2 g, 47.4 mmol) (0) (BTP: tri-tert-butylphosphine) palladium (0) (220 mg, 0.435 mmol) was added and stirred under reflux. After cooling to room temperature, the mixture was extracted with ethyl acetate [EtOAc] and water. The obtained organic layer was dried over MgSO ₄ , concentrated under reduced pressure, and then purified by column chromatography (n-hexane: EtOAc) to obtain 12.5 g Yield 50%). MS: [M + H] &lt; + &gt; = 1169

Synthetic example  2. Compound 4>  synthesis

Compound 4 was synthesized in the same manner as in Reaction Scheme 4 using di ([1,1'-biphenyl] -4-yl) amine instead of the amine group used in Reaction Scheme 4 of Synthesis Example 1.

<Reaction Scheme 5>

  <Intermediate 1-3> <Compound 4>

MS: [M + H] &lt; + &gt; = 1127

Synthetic example  3. Compound 13>  synthesis

Intermediate 13-1 was synthesized according to Reaction Scheme 6 below.

<Reaction Scheme 6>

                                 <Intermediate 13-1>

133 g of 1-bromo-4-chloronaphthalen-2-amine hydrochloride was dissolved in 330 ml of HCl, and the solution was added dropwise to a H ₂ O solution of 35 g of NaNO ₃ at 0 ° C. And stirred for 1 hour. To this solution, hydroborofluoric acid (40%, 530 g) was added and the solid formed after stirring was filtered. The solid was washed with ether, dissolved in benzene, worked up, and purified by column chromatography (benzene) to obtain 61.8 g (Yield 53%) of intermediate 13-1. MS: [M + H] &lt; + &gt; = 259 from intermediate 13-1

Intermediate 13-2 was synthesized according to Reaction Scheme 7 below.

<Reaction Scheme 7>

                        <Intermediate 13-1> <Intermediate 13-2>

2,2'- (3,6-dimethoxynaphthalene-2,7-diyl) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) [2,2'- (3,6-dimethoxynaphthalene-2,7-diyl ) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)] 30mmol 13.2g and intermediate 13-1 60mmol 15.57g, K ₂ CO ₃ Was dissolved in 40 mL of tetrahydrofuran (THF) (200 mL / H ₂ O), refluxed and stirred, and 3 mol% of tetrakis (triphenylphosphine) palladium (0) gave. After 12 hours, the reaction was quenched with NH ₄ Cl, extracted with EtOH and recrystallized from EtOH to obtain 10.9 g (Yield 70%) of Intermediate 13-2. MS: [M + H] &lt; + &gt; = 517 from intermediate 13-2

Intermediate 13-3 was synthesized according to Reaction Scheme 8 below.

<Reaction Scheme 8>

<Intermediate 13-2> <Intermediate 13-3>

Intermediate 13-2, 21 mmol of 10.9 g are dissolved in 100 mL of dimethylformamide (DMF), 14.5 g of K ₂ CO ₃ is added, and the mixture is refluxed and stirred. After 12 hours, the resulting solid was filtered and washed with H ₂ O, ethanol and n-hexane to give 9.2 g (Yield 92%) of intermediate 13-3. MS: [M + H] &lt; + &gt; = 477 from intermediate 13-3

Compound 13 was synthesized according to Reaction Scheme 9 below.

<Reaction Scheme 9>

<Intermediate 13-3> <Compound 13>

Intermediate 13-3 and 19.3 mmol of 9.2 g were dissolved in 500 mL of xylene, and then 5.6 g of NaOtBu (5.9 g) was added thereto. The mixture was refluxed at 150 ° C and stirred, and then N- (4- (tert- butyl) phenyl) -9,9- (Triphenylphosphine) -fluorene-2-amine [N- (4- (tert-butyl) phenyl) -9,9-dimethyl-9H- 5 mol% of palladium (0) (BTP: tri (tert-butylphosphine) palladium (0)) were sequentially added. After 24 hours, the reaction was quenched with NH ₄ Cl, and the residue was purified by column chromatography (n-hexane: EtOAc) to obtain 10.1 g (Yield%) of Compound 13.

MS: [M + H] &lt; + &gt; = 1088 of compound 13

Synthetic example  4. Compound 18>  synthesis

Intermediate 18-1 was synthesized according to Reaction Scheme 10 below.

<Reaction formula 10>

<Intermediate 13-2> <Intermediate 18-1>

10 g of 19.4 mmol of intermediate 13-2 and 10.7 g of K ₂ CO ₃ were dissolved in 200 mL of methylpyrrolidone (NMP), and then 4,4,4,4,4,4,4,4,4-nona-fluoro-4,12 Buta-1,3-diene-1-sulfonyl fluoride [4,4,4,4,4,4,4,4,4-nonafluoro-411-buta-1,3-diyne-1-sulfonyl fluoride] (58.2 mmol, 17.6 g). After the reaction was completed for 24 hours, the reaction mixture was poured into H ₂ O to obtain a solid, which was washed with ethanol and n-hexane to obtain 13.6 g (Yield 65%) of Intermediate 18-1.

MS: [M + H] &lt; + &gt; = 1081 of intermediate 18-1

Intermediate 18-2 was synthesized according to Scheme 11 below.

<Reaction Scheme 11>

<Intermediate 18-1> <Intermediate 18-2>

13.6 g of 12.6 mmol of intermediate 18-1, 3.1 g of methyl 3-mercaptopropanoate (25.5 mmol) and 2.1 eq of diisopropylethylamine (DIPEA) were dissolved in 126 mL of dioxane, refluxed and stirred, and Pd ₂ ) ₃ 4 mol% and 8 mol% Xanthophos were added in sequence. After 12 hours, the reaction was quenched with NH ₄ Cl, extracted with EtOH and recrystallized from EtOH to obtain 7.3 g (Yield 80%) of Intermediate 18-2. MS: [M + H] &lt; + &gt; = 721 of intermediate 18-2

Intermediate 18-3 was synthesized according to Reaction Scheme 12 below.

<Reaction Scheme 12>

<Intermediate 18-2> <Intermediate 18-3>

Intermediate 18-2, 10.1 mmol, 7.3 g was dissolved in 70 mL of dimethylformamide (DMF), 7.3 g of KOtBu was added, and the mixture was stirred under reflux. After 12 hours, the resulting solid was filtered and washed with H ₂ O, ethanol and n-hexane to give 4.8 g (Yield 93%) of intermediate 18-3. MS: [M + H] &lt; + &gt; = 509 from intermediate 18-3

Compound 18 was synthesized according to Reaction Scheme 13 below.

<Reaction Scheme 13>

<Intermediate 18-3> <Compound 18>

9.4 mmol of Intermediate 18-3 was dissolved in 100 mL of xylene, and then 37.6 mmol of NaOtBu (3.6 g, 3.6 g) was added thereto. The mixture was stirred under reflux at 150 ° C and N- (4- (tert- butyl) phenyl) -9,9- (Trifluoromethyl) -fluorene-2-amine [N- (4- (tert-butyl) phenyl) -9,9-dimethyl-9H- 5 mol% of palladium (0) (BTP: tri (tert-butylphosphine) palladium (0)) were sequentially added. After 24 hours, the reaction mixture was quenched with NH ₄ Cl and then purified by column chromatography (n-hexane: EtOAc) to obtain 4.9 mmol of Compound 18 (5.5% yield). MS of compound 18: [M + H] &lt; + &gt; = 1119

Synthetic example  5. Compound 27>  synthesis

Intermediate 27-1 was synthesized according to Reaction Scheme 14 below.

<Reaction Scheme 14>

                                                  <Intermediate 27-1>

2,2 '- (3,6-dimethoxynaphthalene-2,7-diyl) bis (4,4,5,5-tetramethyl-1,3,2-dioxabororane) - (3,6-dimethoxynaphthalene-2,7-diyl) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)] and 13.2 g of 3-bromonaphthalene- 14.3 g of 60 mmol of 3-bromonaphthalene-2,7-diol and 24.9 g of K ₂ CO ₃ were dissolved in 40 mL of tetrahydrofuran (THF) (200 mL) / H ₂ O, refluxed and stirred, and bis (tri- tert-butylphosphine) palladium (0) (BTP: tri (tert-butylphosphine) palladium (0)) were sequentially added. After 12 hours, the reaction was quenched with NH ₄ Cl, extracted with EtOH and recrystallized from EtOH to obtain 10.6 g (Yield 70%) of Intermediate 27-1. MS: [M + H] &lt; + &gt; = 605 for intermediate 27-1

Intermediate 27-2 was synthesized according to Reaction Scheme 15 below.

<Reaction Scheme 15>

         <Intermediate 27-1> <Intermediate 27-2>

Intermediate 27-1 and 21 mmol of 10.6 g were dissolved in 30 mL of methanesulfonic acid (50 mL) and stirred at 100 ° C. After 12 hours, the reaction was quenched with H ₂ O, filtered, and washed with ethanol and hexane. The solid was refluxed with methylpyrrolidone (NMP) and 1,2-dichlorobenzene (DCB), filtered, washed with ethanol and n-hexane to give 18.5 mmol of Yield 88%). MS: [M + H] &lt; + &gt; = 441 from intermediate 27-2

Intermediate 27-3 was synthesized according to Scheme 16 below.

<Reaction Scheme 16>

     <Intermediate 27-2> <Intermediate 27-3>

8.1 g of Intermediate 27-2, 18.5 mmol and 10.5 g of K ₂ CO ₃ were dissolved in 200 mL of methylpyrrolidone (NMP), and then 4,4,4,4,4,4,4,4,4-nonaflo -4,12-Buta-1,3-diene-1-sulfonyl fluoride [4,4,4,4,4,4,4,4-nonafluoro-411-buta-1,3-diyne-1 -sulfonyl fluoride] of 55.5 mmol was added thereto. After the reaction was completed for 24 hours, the reaction mixture was poured into H ₂ O to obtain a solid, which was washed with ethanol and n-hexane to obtain 13.1 mmol (Yield 71%) of intermediate 27-3. MS: [M + H] &lt; + &gt; = 1005 for intermediate 27-3

<Compound 27> was synthesized according to the following Reaction Scheme 17.

<Reaction Scheme 17>

<Intermediate 27-3> <Compound 27>

Intermediate 27-3 and 13.1 mmol of 13.2 g were dissolved in 500 mL of xylene, 11.2 g of K ₃ PO _{4 (} 52.4 mmol) was added, and the mixture was refluxed at 150 ° C. After stirring, N- (4- (tert- butyl) A mixture of 6.3 g of 26.2 mmol of N- (4- (tert-butyl) phenyl) -2-methylaniline and 0.45 g of bis (tri- tert-butylphosphine) palladium (0) )) 5 mol% were sequentially added. After 24 hours, the reaction was quenched with NH ₄ Cl and then purified by column chromatography (n-hexane: EtOAc) to obtain 5.6 g (yield 48%) of Compound 27.

MS: [M + H] &lt; + &gt; = 883

Synthetic example  6. Compound 35>  synthesis

Intermediate 35-1 was synthesized according to Reaction Scheme 18 below.

<Reaction Scheme 18>

                                                  <Intermediate 35-1>

2,2 '- (3,6-dimethoxynaphthalene-2,7-diyl) bis (4,4,5,5-tetramethyl-1,3,2-dioxabororane) (3,6-dimethoxynaphthalene-2,7-diyl) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 14.3 g of 60 mmol of [3-bromonaphthalene-2,6-diol] and 24.9 g of K ₂ CO ₃ were dissolved in 40 mL of tetrahydrofuran (THF) (200 mL) / H ₂ O and refluxed and stirred to obtain bis (tri- tert-butylphosphine) palladium (0) (BTP: tri (tert-butylphosphine) palladium (0)) were sequentially added. After 12 hours, the reaction was quenched with NH ₄ Cl, extracted with EtOH, and 12.1 g (Yield 80%) of Intermediate 35-1 was obtained. MS: [M + H] &lt; + &gt; = 605 for intermediate 35-1

Intermediate 35-2 was synthesized according to Scheme 19 below.

<Reaction Scheme 19>

         <Intermediate 35-1> <Intermediate 35-2>

Intermediate 35-1 (12.1 g) is dissolved in 30 mL of methan sulfonic acid (50 mL) and stirred at 100 ° C. After 12 hours, the reaction was quenched with H ₂ O, filtered, and washed with ethanol and hexane. The solid was refluxed with methylpyrrolidone (NMP) and 1,2-dichlorobenzene (DCB), filtered, washed with ethynol and n-hexane to give 8.5 g of Yield 81%). MS: [M + H] &lt; + &gt; = 441 from intermediate 35-2

Intermediate 35-3 was synthesized according to Reaction Scheme 20 below.

<Reaction Scheme 20>

      <Intermediate 35-2> <Intermediate 35-3>

To 200 mL of methylpyrrolidone (NMP) were dissolved 8.5 g of Intermediate 35-2, 19.4 mmol and 10.7 g of K ₂ CO ₃ , and 4,4,4,4,4,4,4,4,4-nonafluoro- 4,12-Buta-1,3-diene-1-sulfonyl fluoride [4,4,4,4,4,4,4,4-nonafluoro-411-buta-1,3- sulfonyl fluoride] (58.2 mmol, 17.6 g). After the reaction was completed for 24 hours, the reaction mixture was poured into H ₂ O to obtain a solid, which was washed with ethanol and n-hexane to obtain 12.7 g (Yield 65%) of Intermediate 35-3. MS: [M + H] &lt; + &gt; = 1005 for intermediate 35-3

<Compound 35> was synthesized according to the following Reaction Scheme 21.

<Reaction Scheme 21>

<Intermediate 35-3> <Compound 35>

Intermediate 35-3 and 12.7 mmol of 12.7 g were dissolved in 500 mL of xylene, 10.8 g of K ₃ PO ₄ 50 mmol was added thereto, and the mixture was refluxed at 150 ° C. After stirring, 2-methyl-N-phenylaniline 25.2 mmol and 5 mol% of bis (tri-tert-butylphosphine) palladium (0) (BTP: Bis (tri-tert-butylphosphine) palladium (0)) were sequentially added. After 24 hours, the reaction was quenched with NH ₄ Cl, and the residue was purified by column chromatography (n-hexane: EtOAc) to obtain 5.1 g (yield 52%) of Compound 35.

MS: [M + H] &lt; + &gt; = 771 from 35

< Example >

Example  One.

A thin glass substrate coated with ITO (indium tin oxide) having a thickness of 1300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

The following compound [HI-A] was vacuum deposited on the ITO transparent electrode prepared above to a thickness of 600 Å to form a hole injection layer. The following compound [HAT-CN] (50 Å) and the following compound [HT-A] (600 Å) were sequentially vacuum-deposited on the hole injection layer to form a hole transport layer.

Subsequently, the following compounds [BH] and [BD] were vacuum deposited on the hole transport layer at a weight ratio of 25: 1 at a thickness of 200 ANGSTROM to form a light emitting layer.

Then, [BH-A] and Compound 1 were vacuum-deposited to a thickness of 200 Å at a weight ratio of 25: 1 to form a light emitting layer. Then, [ET-A] and Liq were deposited at a ratio of 1: 1 to form 300 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 10 Å to form a cathode. .

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, the deposition rate of lithium fluoride was 0.3 Å / sec for aluminum and 2 Å / sec for aluminum, ^- holding a ⁷ to 5 Х 10 ^-8 torr, an organic light emitting device was produced.

            [HI-A] [HT-A]

    [HAT-CN] [Liq]

   [BH-A] [BH-B] [BH-C]

        [BD-A] [BD-B]

Example  2.

An organic luminescent device was prepared in the same manner as in Example 1, except that [BH-B] was used in place of the host [BH-A] in Example 1 above.

Example  3.

An organic luminescent device was prepared in the same manner as in Example 1, except that [BH-C] was used instead of the host [BH-A] in Example 1. [

Example  4.

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

Example  5.

An organic luminescent device was prepared in the same manner as in Example 1 except that [BH-B] was used in place of the host [BH-A].

Example  6.

An organic luminescent device was prepared in the same manner as in Example 1 except that [BH-C] was used in place of the host [BH-A].

Example  7.

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 13 was used instead of Compound 1 in Example 1.

Example  8.

An organic luminescent device was fabricated in the same manner as in Example 1 except that [BH-B] was used instead of the host [BH-A].

Example  9.

An organic light emitting device was prepared in the same manner as in Example 1 except that Compound 18 was used instead of Compound 1 in Example 1.

Example  10.

An organic luminescent device was prepared in the same manner as in Example 1 except that [BH-B] was used in place of the host [BH-A] in Example 9.

Example  11.

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 27 was used instead of Compound 1 in Example 1.

Example  12.

An organic luminescent device was prepared in the same manner as in Example 1 except that [BH-B] was used in place of the host [BH-A].

Example  13.

An organic luminescent device was prepared in the same manner as in Example 1 except that [BH-C] was used in place of the host [BH-A].

Example  14.

An organic light emitting device was prepared in the same manner as in Example 1 except that Compound 35 was used instead of Compound 1 in Example 1.

Example  15.

An organic luminescent device was prepared in the same manner as in Example 1 except that [BH-B] was used in place of the host [BH-A].

Example  16.

An organic luminescent device was fabricated in the same manner as in Example 1 except that [BH-C] was used instead of the host [BH-A].

< Comparative Example >

Comparative Example  One.

An organic luminescent device was prepared in the same manner as in Example 1 except that [BD-A] was used in place of the compound 1 in Example 1 above.

Comparative Example  2.

An organic luminescent device was prepared in the same manner as in Example 1 except that [BD-B] was used in place of the compound 1 in Example 1 above.

Comparative Example  3.

An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that [BH-B] was used in place of [BH-A] in Comparative Example 1. [

Comparative Example  4.

An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that [BH-C] was used in place of [BH-A] in Comparative Example 1. [

Comparative Example  5.

An organic light emitting device was prepared in the same manner as in Comparative Example 2 except that [BH-B] was used in place of [BH-A] in Comparative Example 2. [

Comparative Example  6.

An organic light emitting device was prepared in the same manner as in Comparative Example 2 except that [BH-C] was used in place of [BH-A] in Comparative Example 2. [

The driving voltage and the luminous efficiency were measured at a current density of 10 mA / cm &lt; ² &gt; at the current density of 20 mA / cm &lt; ² &gt; and the time (T ₉₀ ) Respectively. The results are shown in Table 1 below.

number Host Voltage (V) Efficiency (Cd / A) The color coordinates (x, y) Life (hr) at 10 mA / cm ² at 10 mA / cm ² T ₉₀ at 20 mA / cm ² Example 1 BH-A 3.62 5.32 (0.133, 0.118) 195 Example 2 BH-B 3.42 5.43 (0.133, 0.118) 225 Example 3 BH-C 3.72 5.36 (0.134, 0.119) 260 Example 4 BH-A 3.70 5.50 (0.134, 0.122) 280 Example 5 BH-B 3.62 5.32 (0.134, 0.123) 265 Example 6 BH-C 3.72 5.20 (0.134, 0.125) 320 Example 7 BH-A 3.54 5.68 (0.134, 0.125) 285 Example 8 BH-B 3.52 5.76 (0.134, 0.126) 330 Example 9 BH-A 3.70 5.48 (0.134, 0.127) 270 Example 10 BH-B 3.52 5.54 (0.134, 0.127) 290 Example 11 BH-A 3.53 5.63 (0.134, 0.123) 315 Example 12 BH-B 3.38 5.72 (0.134, 0.125) 320 Example 13 BH-C 3.50 5.56 (0.134, 0.126) 380 Example 14 BH-A 3.80 5.45 (0.133, 0.116) 250 Example 15 BH-B 3.66 5.30 (0.133, 0.116) 230 Example 16 BH-C 3.70 5.10 (0.133, 0.117) 220 Comparative Example 1 BH-A 3.75 5.10 (0.133, 0.128) 120 Comparative Example 2 BH-A 4.10 4.30 (0.133, 0.130) 75 Comparative Example 3 BH-B 3.80 4.63 (0.133, 0.128) 70 Comparative Example 4 BH-C 4.20 4.32 (0.133, 0.130) 90 Comparative Example 5 BH-B 3.70 4.75 (0.133, 0.133) 55 Comparative Example 6 BH-C 4.30 4.32 (0.133, 0.133) 85

From the results shown in Table 1, the compound represented by Formula 1 according to the present invention exhibits high luminescence efficiency and long lifetime characteristics in a blue organic light emitting device. Specifically, the organic electroluminescent devices of Examples 1 to 16, which were prepared including the compound according to the present invention, were prepared by the same procedure as in Comparative Examples 1, 3 and 4 using the pyrene-based compound and Comparative Example 2 , 5 and 6, the efficiency was high, and the lifetime was excellent.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: Hole injection layer
6: hole transport layer
7:
8: Electron transport layer

Claims (15)

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

In Formula 1,
X1 and X2 are the same or different and each independently O, S or CRaRb,
Ra, Rb and R1 to R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L1 and L2 are the same or different from each other and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
RA1 to RA4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl 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 heterocycle,
A1 and A2 are the same or different and each independently represents a monocyclic or polycyclic substituted or unsubstituted ring,
n1 and n2 are each an integer of 0 to 2, and when n1 and n2 are each 2, the substituents in the parentheses of 2 or more are the same or different from each other,
m1 and m2 are each 0 or 1, and m1 + m2 is 1 or more. The method according to claim 1,
(1) is represented by any one of the following formulas (2) to (4):
(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,
X1 and X2 and R1 to R6, n1, n2, L1, L2, RA1 to RA4, m1 and m2 are as defined in formula (1)
Any one of W1 and W2 is a direct bond and the remainder is O, S or CRR '
W3 and W4 is a direct bond and the remainder is O, S or CR " R "
R, R ', R &quot;, R "' and R 7 to R 12 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,
n11 to n16 are each an integer of 0 to 4, and when n11 to n16 are each 2, the substituents in the parentheses of 2 or more are the same or different from each other. The method according to claim 1,
The compound represented by the formula (1) is represented by any one of the following formulas (5) to (7):
[Chemical Formula 5]

[Chemical Formula 6]

(7)

In Formulas 5 to 7,
X1, X2 and R1 to R6, L1, L2 and RA1 to RA4 have the same definitions as in formula (1)
Any one of W1 and W2 is a direct bond and the remainder is O, S or CRR '
W3 and W4 is a direct bond and the remainder is O, S or CR " R "
R, R ', R &quot;, R "' and R 7 to R 12 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,
n21 and n22 are each 0 or 1,
each of n23 to n26 is an integer of 0 to 4, and when n23 to n26 are each 2 or more, the substituents in the parentheses of 2 or more are the same or different,
n27 and n28 are each an integer of 0 to 3, and when n27 and n28 are each 2 or more, the substituents in the parentheses of 2 or more are the same or different from each other. The method according to claim 1,
(1) is represented by any one of the following structures:

Compound 1 Compound 2 Compound 3

Compound 4 Compound 5 Compound 6

Compound 7 Compound 8 Compound 9

Compound 10 Compound 11 Compound 12

Compound 13 Compound 14 Compound 15

Compound 16 Compound 17 Compound 18

Compound 19 Compound 20 Compound 21

Compound 22 Compound 23 Compound 24

Compound 25 Compound 26 Compound 27

Compound 28 Compound 29 Compound 30

Compound 31 Compound 32 Compound 33

Compound 34 Compound 35 Compound 36. A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to any one of claims 1 to 4. The organic light- Light emitting element. The method of claim 5,
Wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound. The method of claim 5,
Wherein the organic material layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer comprises the compound. The method of claim 5,
Wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. The organic light emitting device according to claim 5, wherein the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the compound. The method of claim 5,
Wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises a compound represented by the following formula (1A):
&Lt; EMI ID =

In the above formula (1A)
L103 to L106 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar5 to Ar8 are the same or different and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R24 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
p is an integer of 0 to 6,
When p is 2 or more, the substituents in the parentheses are the same or different. The method of claim 10,
L103 to L106 are the same or different and are each independently a direct bond; Or an organic electroluminescent element selected from the following structures:

. The method of claim 10,
Ar5 to Ar8 are the same or different from each other and each independently hydrogen; Or an organic electroluminescent element selected from the following structures:

. [6] The organic light emitting device of claim 5, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises a compound represented by the following Formula 1B:
&Lt; RTI ID = 0.0 &

In the above formula (1B)
L107 to L109 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar9 to Ar11 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R25 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
q is an integer of 0 to 7,
When q is 2 or more, the substituents in the parentheses are the same or different from each other. 14. The method of claim 13,
L107 to L109 are the same or different and are each independently a direct bond; Or an organic electroluminescent element selected from the following structures:

. 14. The method of claim 13,
Wherein Ar9 to Ar11 are the same or different from each other and each independently selected from among the following structures:

.

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