KR102187984B1 - Heterocyclic compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification provides a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

Description

Heterocyclic compound and organic light emitting device comprising the same TECHNICAL FIELD

The present specification relates to a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0022090 filed with the Korean Intellectual Property Office on February 23, 2018, the entire contents of which are incorporated herein.

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

Development of a new material for the organic light emitting device as described above is continuously required.

US 20140299851 A1

An object of the present specification is to provide a compound capable of improving efficiency, driving voltage, and/or lifetime characteristics when used in an organic light-emitting device, and an organic light-emitting device including the same.

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

[Formula 1]

In Formula 1,

R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted C ₁₀ or more aryl group, -N(R5)(R6), -N(R7)(R8), -N(R9)(R10) Or a substituted or unsubstituted N-containing heterocyclic group,

R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, -N(R11)(R12), -N(R13)(R14), -N(R15)(R16) or substituted or It is an unsubstituted N-containing heterocycle,

R5 to R7 and R11 to R13 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,

R8 to R10 and R14 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted heteroaryl group,

a is 1 or 2, b is 1 or 2, c is an integer from 1 to 4, d is an integer from 1 to 4,

If a is 2, R1 is the same or different from each other, if b is 2, R2 is the same or different from each other, if c is 2 or more, R3 is the same or different from each other, and if d is 2 or more, R4 is the same or different from each other.

In addition, an exemplary embodiment of the present specification is an organic light emitting device including a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is It provides an organic light-emitting device comprising the compound according to an exemplary embodiment of the specification.

The compound described herein can be used as a material for an organic material layer of an organic light emitting device. The compound according to at least one exemplary embodiment may improve efficiency, driving voltage, and/or life characteristics in an organic light-emitting device. In particular, the compounds described herein may be used as a hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection material.

More specifically, the compound according to an exemplary embodiment of the present invention has a structure having a high electron-accepting capacity and has excellent heat resistance, so that an appropriate deposition temperature can be maintained when fabricating an organic light-emitting device. In addition, the sublimation temperature is high, so it is possible to achieve high purity by a sublimation purification method, and does not cause contamination of the deposition apparatus or the organic light emitting device when manufacturing the organic light emitting device.

1 shows an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
2 shows an organic light-emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron transport layer 7 and a cathode 4 .
3 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (8), a light emitting layer (3), an electron injection and transport layer (9) and a cathode (4). It shows an organic light emitting device made of.

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

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

는 연결 부위를 의미한다In this specification,

Means connection site

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

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group; Alkoxy group; Aryloxy group; Silyl group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Amine group; And substituted or unsubstituted with one or more groups selected from the group consisting of a heterocyclic group, or substituted or unsubstituted with a group to which two or more groups selected from the group are linked.

For example, "a group in which two or more groups are linked" may be a naphthylphenyl group. That is, a naphthyl group may be a substituted aryl group, or may be interpreted as a substituent connected with two aryl groups.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the silyl group may be represented by the formula of -SiR _a R _b R _c , wherein R _a , R _b and R _c are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc., but is not limited thereto. Does not.

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, n-pentyl, isopentyl, neopentyl , tert-pentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, n- Octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methyl Hexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. May be, but is not limited thereto.

Substituents including an alkyl group, an alkoxy group, and other alkyl group moieties described in the present specification include all of a straight chain or a branched form.

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the amine group means -NH ₂ .

In the present specification, the substituted amine group is -NR _x R _y , R _x and R _y are the same as or different from each other, and each independently deuterium; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

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

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

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

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

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

Spirofluorenyl groups such as,

(9,9-dimethylfluorenyl group), and

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

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 1 to 30. Examples of heterocyclic groups include pyridinyl group, pyrrolyl group, pyrimidinyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl Group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, pyrazinyl group, oxazinyl group, thiazinyl group, di Oxynyl group, triazinyl group, tetrazinyl group, quinolinyl group, isoquinolinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, acridinyl group, xanthenyl group, phenanthridinyl group, dia Xanaphthalenyl group, triazindenyl group, indolyl group, indolinyl group, indolizinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, benzothiazolyl group, Benzoxazolyl group, benzimidazolyl group, benzothiophenyl group, benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, indolocarbazolyl group, Indenocarbazolyl group, phenazinyl group, imidazopyridinyl group, phenoxazinyl group, phenanthridinyl group, phenanthrolinyl group, phenothiazinyl group, imidazopyridinyl group, imida There is a zophenanthridinyl group, and the like, but is not limited thereto.

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

According to an exemplary embodiment of the present specification, the organic light emitting device including the compound according to the exemplary embodiment of the present specification in the emission layer can be applied to a green organic device having a long wavelength, and may have characteristics of a low driving voltage and a high device lifetime. have.

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

The compound of Formula 1 includes at least one R1, at least one R2, at least one R3, and at least one R4, thereby adjusting the highest occupied molecular orbital (HOMO) energy level of the compound to extend the emission wavelength region to the green region. Make it possible. The R1 to R4 prevent overlapping between molecules, and if the types of R1 to R4 are different, the band gap of the compound can be adjusted, and the emission wavelength can also be adjusted.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 4.

[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,

The definitions of R1 to R4 and a to d are the same as in Formula 1.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted (C _10-60 ) aryl group, -N(R5)(R6), -N(R7) )(R8), -N(R9)(R10) or a substituted or unsubstituted N-containing (C _2-60 ) heterocyclic group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted (C _10-36 ) aryl group, -N(R5)(R6), -N(R7 )(R8), -N(R9)(R10) or a substituted or unsubstituted N-containing (C _2-30 ) heterocyclic group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted (C _10-25 ) aryl group, -N(R5)(R6), -N(R7) )(R8), -N(R9)(R10) or a substituted or unsubstituted N-containing (C _2-20 ) heterocyclic group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted (C _10-20 ) aryl group, -N(R5)(R6), -N(R7 )(R8), -N(R9)(R10) or a substituted or unsubstituted N-containing (C _2-16 ) heterocyclic group.

According to an exemplary embodiment of the present specification, if R1 or R2 is a substituted C ₁₀ or more aryl group, the substituent of the substituted C ₁₀ or more aryl group is deuterium, a halogen group, a cyano group, an alkoxy group, an alkyl group, or an aryl group. .

According to an exemplary embodiment of the present specification, if R1 or R2 is a substituted C ₁₀ or more aryl group, the substituent of the substituted C ₁₀ or more aryl group is deuterium, halogen group, cyano group, (C _1-10 ) alkoxy group , (C _1-10 ) alkyl group or (C _6-20 ) aryl group.

According to an exemplary embodiment of the present specification, if R1 or R2 is a substituted C ₁₀ or more aryl group, the substituent of the substituted C ₁₀ or more aryl group is deuterium, a halogen group, a cyano group, (C _1-6 ) an alkoxy group , (C _1-6 ) alkyl group or (C _6-12 ) aryl group.

According to an exemplary embodiment of the present specification, if R1 or R2 is a substituted N-containing heterocycle, the substituent of the N-containing heterocycle is deuterium, a halogen group, a cyano group, an alkoxy group, an alkyl group, or an aryl group.

According to an exemplary embodiment of the present specification, if R1 or R2 is a substituted N-containing heterocycle, the substituent of the N-containing heterocycle is deuterium, a halogen group, a cyano group, (C _1-10 ) an alkoxy group, (C _{1 -10} ) an alkyl group or a (C _6-20 ) aryl group.

According to an exemplary embodiment of the present specification, if R1 or R2 is a substituted N-containing heterocycle, the substituent of the N-containing heterocycle is deuterium, a halogen group, a cyano group, (C _1-6 ) an alkoxy group, (C _{1 -6} ) an alkyl group or a (C _6-12 ) aryl group.

According to an exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, -N(R11)(R12), -N(R13)(R14),- N(R15)(R16) or a substituted or unsubstituted N-containing (C _2-60 ) heterocyclic group.

According to an exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted (C _6-30 ) aryl group, -N(R11)(R12), -N(R13 )(R14), -N(R15)(R16) or a substituted or unsubstituted N-containing (C _2-30 ) heterocyclic group.

According to an exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted (C _6-20 ) aryl group, -N(R11)(R12), -N(R13 )(R14), -N(R15)(R16) or a substituted or unsubstituted N-containing (C _2-20 ) heterocyclic group.

According to an exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted (C _6-12 ) aryl group, -N(R11)(R12), -N(R13 )(R14), -N(R15)(R16) or a substituted or unsubstituted N-containing (C _2-16 ) heterocyclic group.

According to an exemplary embodiment of the present specification, if R3 or R4 is a substituted aryl group, the substituent of the aryl group is deuterium, a halogen group, a cyano group, an alkoxy group, an alkyl group, or an aryl group.

According to an exemplary embodiment of the present specification, if R3 or R4 is a substituted aryl group, the substituent of the aryl group is an alkyl group.

According to an exemplary embodiment of the present specification, if R3 or R4 is a substituted N-containing heterocyclic group, the substituent of the N-containing heterocyclic group is deuterium, a halogen group, a cyano group, an alkoxy group, an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, if R3 or R4 is a substituted N-containing heterocyclic group, the substituent of the N-containing heterocyclic group is deuterium, a halogen group, a cyano group, (C _1-10 ) an alkoxy group, (C _1-10 ) an alkyl group or a (C _6-20 ) aryl group.

According to an exemplary embodiment of the present specification, if R3 or R4 is a substituted N-containing heterocyclic group, the substituent of the N-containing heterocyclic group is deuterium, a halogen group, a cyano group, (C _1-6 ) an alkoxy group, ( It is a C _1-6 ) alkyl group or a (C _6-12 ) aryl group.

According to an exemplary embodiment of the present specification, if R3 or R4 is a substituted N-containing heterocyclic group, the substituent of the N-containing heterocyclic group is an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, R5 to R7 and R11 to R13 are the same as or different from each other, and each independently a substituted or unsubstituted (C _6-30 ) aryl group.

According to an exemplary embodiment of the present specification, R5 to R7 and R11 to R13 are the same as or different from each other, and each independently a substituted or unsubstituted (C _6-25 ) aryl group.

According to an exemplary embodiment of the present specification, R5 to R7 and R11 to R13 are the same as or different from each other, and each independently a substituted or unsubstituted (C _6-20 ) aryl group.

According to an exemplary embodiment of the present specification, R5 to R7 and R11 to R13 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group.

According to an exemplary embodiment of the present specification, if R5 to R7 and R11 to R13 are a substituted aryl group, the substituent of the aryl group is deuterium, a halogen group, a cyano group, an alkoxy group, an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, if R5 to R7 and R11 to R13 are a substituted aryl group, the substituent of the aryl group is deuterium, a halogen group, a cyano group, (C _1-10 ) an alkoxy group, (C _{1 -10} ) an alkyl group or a (C _6-20 ) aryl group.

According to an exemplary embodiment of the present specification, if R5 to R7 and R11 to R13 are a substituted aryl group, the substituent of the aryl group is deuterium, a halogen group, a cyano group, (C _1-6 ) an alkoxy group, (C _{1 -6} ) an alkyl group or a (C _6-12 ) aryl group.

According to an exemplary embodiment of the present specification, if the R5 to R7 and R11 to R13 are a substituted aryl group, the substituent of the aryl group is a methyl group; t-butyl group; Cyano group; Fluoro group; Methoxy group; Or a phenyl group.

In the exemplary embodiment of the present specification, R8 to R10 and R14 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted heteroaryl group containing O or S.

In the exemplary embodiment of the present specification, R8 to R10 and R14 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted (C _2-30 ) heteroaryl group.

In the exemplary embodiment of the present specification, R8 to R10 and R14 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted (C _2-20 ) heteroaryl group.

In the exemplary embodiment of the present specification, R8 to R10 and R14 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted (C _2-16 ) heteroaryl group.

In the exemplary embodiment of the present specification, R8 to R10 and R14 to R16 are the same as or different from each other, and each independently a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group.

In the exemplary embodiment of the present specification, R8 to R10 and R14 to R16 are the same as or different from each other, and each independently a dibenzofuranyl group or a dibenzothiophenyl group.

In the exemplary embodiment of the present specification, if R8 to R10 and R14 to R16 are a substituted heteroaryl group, the substituent of the heteroaryl group is deuterium, a halogen group, a cyano group, an alkoxy group, an alkyl group or an aryl group.

In the exemplary embodiment of the present specification, if R8 to R10 and R14 to R16 are substituted heteroaryl groups, the substituents of the heteroaryl group are deuterium, halogen groups, cyano groups, (C _1-10 ) alkoxy groups, ( It is a C _1-10 ) alkyl group or a (C _6-20 ) aryl group.

In an exemplary embodiment of the present specification, if R8 to R10 and R14 to R16 are a substituted heteroaryl group, the substituent of the heteroaryl group is deuterium, a halogen group, a cyano group, (C _1-6 ) an alkoxy group, ( It is a C _1-6 ) alkyl group or a (C _6-12 ) aryl group.

In an exemplary embodiment of the present specification, at least one of R5 to R7 and R11 to R13 is a substituted aryl group.

In an exemplary embodiment of the present specification, at least one of R5 to R7 and R11 to R13 is an aryl group unsubstituted or substituted with deuterium, a halogen group, a cyano group, an alkoxy group, an alkyl group, or an aryl group.

In an exemplary embodiment of the present specification, at least one of R5 to R7 is an aryl group substituted with deuterium, a halogen group, a cyano group, an alkoxy group, an alkyl group, or an aryl group.

In an exemplary embodiment of the present specification, at least one of R11 to R13 is an aryl group substituted with deuterium, a halogen group, a cyano group, an alkoxy group, an alkyl group, or an aryl group.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently -N(R5)(R6), -N(R7)(R8), -N(R9)(R10) or It is a substituted or unsubstituted N-containing heterocyclic group.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently -N(R5)(R6), -N(R7)(R8), or -N(R9)(R10). .

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted N-containing heterocyclic group.

In the exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently -N(R11)(R12), -N(R13)(R14), -N(R15)(R16) or It is a substituted or unsubstituted N-containing heterocyclic group.

In the exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and are each independently -N(R11)(R12), -N(R13)(R14), or -N(R15)(R16). .

In the exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted N-containing heterocyclic group.

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

In an exemplary embodiment of the present specification, R3 and R4 are the same.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted C ₁₀ or more aryl group, -N(R5)(R6), -N(R7)(R8 ), -N(R9)(R10) or any one of the following formulas HAr1 to Ar5,

R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, -N(R11)(R12), -N(R13)(R14), -N(R15)(R16) or the following formula It is any one of HAr1 to Ar5.

In the HAr1 to HAr5,

R21 to R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Alkoxy group; Alkyl group; Or an aryl group,

R33 and R34 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl group; Or an aryl group, R33 and R34 are each a phenyl group and are bonded to each other to deuterium; Halogen group; Cyano group; Alkoxy group; Alkyl group; Or to form a substituted or unsubstituted fluorene ring with an aryl group,

a21 to a28, a31 and a32 are the same as or different from each other, and each independently an integer of 0 to 4,

If a21 is 2 or more, R21 is the same or different, if a22 is 2 or more, R22 is the same or different, and if a23 is 2 or more, R23 is the same or different, and if a24 is 2 or more, R24 is the same or different. And, if a25 is 2 or more, R25 is the same as or different from each other, if a26 is 2 or more, R26 is the same or different, and if a27 is 2 or more, R27 is the same or different, and if a28 is 2 or more, R28 is the same. Or different, and if a31 is 2 or more, R31 is the same as or different from each other, and if a32 is 2 or more, R32 is the same or different from each other,

The definition of R5 to R16 is the same as in Formula 1.

In the exemplary embodiment of the present specification, R21 to R32 are each hydrogen.

In the exemplary embodiment of the present specification, R33 and R34 are each a phenyl group and are bonded to each other to form a fluorene ring.

In an exemplary embodiment of the present specification, HAr5 is represented by the following HAr5-1.

In the formula HAr5-1, the definitions of R31, R32, a31 and a32 are as defined in HAr5,

R35 and R36 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Alkoxy group; Alkyl group; Or an aryl group,

a35 is an integer of 0 to 4, and if a35 is 2 or more, R35 is the same as or different from each other,

a36 is an integer of 0 to 4, and when a36 is 2 or more, R36 is the same as or different from each other.

In the exemplary embodiment of the present specification, R35 and R36 are each hydrogen.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 5 to 7.

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 5 to 7, R1 to R4 and a to d are defined as in Formula 1.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 8 to 10 below.

[Formula 8]

[Formula 9]

[Formula 10]

In Formulas 8 to 10, the definitions of R1 to R4 are the same as in Formula 1.

In an exemplary embodiment of the present invention, the compound represented by Formula 1 is any one selected from the following compounds.

In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In general, it is easy to adjust the energy bandgap by introducing a substituent into a core structure having a large energy bandgap, but when the energy bandgap is small, it is difficult to greatly adjust the energy bandgap by introducing a substituent. In addition, in the present invention, the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure of the above structure.

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

The compound of Formula 1 described above can be prepared using materials and reaction conditions known in the art.

The organic light-emitting device according to the present invention is an organic light-emitting device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer is represented by Formula 1 Contains compounds.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present specification may further include at least one of a hole injection layer, a hole buffer layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer in addition to the emission layer as an organic material layer. have. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 1 above.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes 0.1% by weight or more and 10% by weight or less based on 100% by weight of the total emission layer.

In the exemplary embodiment of the present application, the light emitting layer including the compound represented by Formula 1 further includes a host compound.

In the exemplary embodiment of the present application, the emission layer including the compound represented by Formula 1 further includes two different host compounds. When two different types of hosts are used as the host of the light emitting layer, the life and efficiency of the device are further improved.

As a material of the light-emitting layer, a material capable of emitting light in a visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may also include a host compound and a dopant compound. The host compound includes a condensed aromatic ring derivative or a heterocycle-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladders. Type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

The dopant compound of the light emitting layer includes an aromatic amine derivative, a styrylamine compound, an aromatic hydrocarbon compound substituted with a carbazole group, a boron complex, a fluoranthene compound, a metal complex, and the like. As the aromatic amine derivative, as a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, pyrene, anthracene, chrysene, periflanthene and the like having an arylamine group may be used. As the styrylamine compound, a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine may be used. Examples of the styrylamine compound include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. The metal complex may be an iridium complex or a platinum complex, but is not limited thereto.

According to an exemplary embodiment of the present specification, the host is a compound represented by any one of the following Chemical Formulas 31 to 39.

[Formula 31]

In Formula 31,

X1 is a single bond; O; S; Or CRmRn,

Rm and Rn are the same as or different from each other, and each independently hydrogen; Alkyl group; Or an aryl group,

R40 and R41 are the same as or different from each other, and each independently hydrogen; Alkyl group; Aryl group; Or a heteroaryl group,

G1 to R4 are the same as or different from each other, and each independently an aryl group,

b1 is an integer of 0 to 8, b2 is an integer of 0 to 8, b1+b2 is 1 or more,

는 서로 같거나 상이하고, b2가 2 이상이면

는 서로 같거나 상이하며,if b1 is 2 or more

Is the same as or different from each other, and if b2 is 2 or more,

Are the same or different from each other,

m1 is an integer of 0 to 8, and when m1 is 2 or more, R31 is the same as or different from each other,

m2 is an integer from 0 to 8, and when m2 is 2 or more, R30 is the same as or different from each other,

[Formula 32]

In Formula 32,

X2 is O or N(R42),

R42 is an aryl group,

L11 is a direct bond; Or an arylene group,

G5 is a heteroaryl group containing 2 or more N substituted or unsubstituted with an aryl group,

G6 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

[Formula 33]

In Chemical Formula 33,

X3 is O or S,

L12 is a direct bond; Or an arylene group,

m3 is an integer of 0 to 3, and when m3 is 2 or more, L12 is the same as or different from each other,

G7 is an aryl group,

G8 is a heteroaryl group substituted or unsubstituted with a cyano group and including O, S or N,

[Formula 34]

In Formula 34,

G9 and G10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An aryl group unsubstituted or substituted with a cyano group; Or a heteroaryl group unsubstituted or substituted with a cyano group,

e is an integer from 0 to 8,

a9 is an integer from 0 to 7, and when a9 is 2 or more, G9 is the same as or different from each other,

a10 is an integer from 0 to 8, and when a10 is 2 or more, G10 is the same as or different from each other,

[Formula 35]

In Formula 35,

L13 is a substituted or unsubstituted b-valent aryl group; Or b is a heteroaryl group,

G11 and G12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Or a heteroaryl group including O or S,

b13 is an integer of 1 to 3, and when b13 is 2 or more, L13 is the same as or different from each other,

는 서로 같거나 상이하며,f is 1 or 2, and if f is 2

Are the same or different from each other,

[Formula 36]

In Formula 36,

X5 and X6 are the same as or different from each other, and each independently N(R43), O or S,

R43 is an aryl group,

Y1 to Y4 are the same as or different from each other, and each independently N; CH; Or C-CN,

L14 is a direct bond; An arylene group unsubstituted or substituted with a cyano group or a heteroaryl group; Or a heteroarylene group unsubstituted or substituted with a cyano group,

b14 is an integer of 0 to 4, and when b14 is 2 or more, L14 is the same as or different from each other,

[Formula 37]

In Formula 37,

X7 is O or S,

One of X8 and X9 is O or S, and the other is a direct bond,

G13 and G14 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a cyano group,

G15 is hydrogen; Or an aryl group,

[Formula 38]

In Formula 38,

X10 is O or S,

L15 and L16 are the same as or different from each other, and each independently a direct bond; An arylene group unsubstituted or substituted with a cyano group; Or a heteroarylene group unsubstituted or substituted with a cyano group,

G16 is the following formula a,

[Formula a]

In the formula (a),

Y5 is CH or N,

g is an integer from 0 to 7,

G17 is hydrogen; Aryl group; Or a heterocyclic group unsubstituted or substituted with an aryl group,

b16 is 1 or 2, and if b16 is 2, -L16-G16 is the same as or different from each other,

[Formula 39]

G18-L19-G19

In Chemical Formula 39,

G18 is an aryl group; Or a heteroaryl group,

L19 is a direct bond; Or an arylene group,

G19 is an aryl group; Or a heteroaryl group.

In the exemplary embodiment of the present specification, G1 to G4 are the same as or different from each other, and each independently is an aryl group having 6 to 24 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms.

In the exemplary embodiment of the present specification, G1 to G4 are each independently a phenyl group.

In the exemplary embodiment of the present specification, R40 and R41 are the same as or different from each other, and each independently hydrogen; Aryl group having 6 to 18 carbon atoms; Or a C2-C24 heteroaryl group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, R40 and R41 are the same as or different from each other, and each independently a benzo[4,5]-thieno[3,2-d]pyrimidinyl group substituted with a phenyl group.

In the exemplary embodiment of the present specification, b1 is 0 and m1 is 1.

In the exemplary embodiment of the present specification, L11 is a direct bond; Or an arylene group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, L11 is a direct bond; Or an arylene group having 6 to 12 carbon atoms.

In the exemplary embodiment of the present specification, L11 is a direct bond; Or a phenylene group.

In the exemplary embodiment of the present specification, G5 is a C2-C24 heteroaryl group containing 2 or more N substituted or unsubstituted with an aryl group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, G5 is a C2 to C18 heteroaryl group containing 2 or more N substituted or unsubstituted with an aryl group having 6 to 12 carbon atoms.

In the exemplary embodiment of the present specification, G5 is a pyrimidinyl group unsubstituted or substituted with one or more substituents of a phenyl group or a biphenyl group; A benzimidazolyl group unsubstituted or substituted with one or more substituents of a phenyl group or a biphenyl group; Or a triazinyl group unsubstituted or substituted with one or more substituents among a phenyl group or a biphenyl group.

In the exemplary embodiment of the present specification, G6 is an aryl group having 6 to 18 carbon atoms unsubstituted or substituted with a silyl group or an aryl group; Or it is a C2-C18 heteroaryl group.

In the exemplary embodiment of the present specification, G6 is an aryl group having 6 to 12 carbon atoms unsubstituted or substituted with a silyl group or an aryl group; Or it is a C2-C12 heteroaryl group.

In the exemplary embodiment of the present specification, G6 is a phenyl group; Biphenyl group; Triphenylsilylphenyl group; Or a dibenzofuranyl group.

In the exemplary embodiment of the present specification, G7 is an aryl group having 6 to 24 carbon atoms.

In the exemplary embodiment of the present specification, G7 is an aryl group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, G7 is a phenyl group; Or a triphenylenyl group.

In the exemplary embodiment of the present specification, L12 is a direct bond; Or an arylene group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, L12 is a direct bond; Or an arylene group having 6 to 12 carbon atoms.

In the exemplary embodiment of the present specification, G8 is a carbazolyl group unsubstituted or substituted with a cyano group; Dibenzothiophenyl group; Or a dibenzofuranyl group.

In the exemplary embodiment of the present specification, G9 and G10 are the same as or different from each other, and each independently hydrogen; Or it is a C2-C16 heteroaryl group.

In the exemplary embodiment of the present specification, G9 and G10 are the same as or different from each other, and each independently hydrogen; Or a dibenzofuranyl group.

In the exemplary embodiment of the present specification, e is 0 or 1.

In the exemplary embodiment of the present specification, L13 is a substituted or unsubstituted b-valent aryl group having 6 to 16 carbon atoms; Or a b-valent heteroaryl group having 2 to 16 carbon atoms.

In the exemplary embodiment of the present specification, L13 is a substituted or unsubstituted b-valent aryl group having 6 to 12 carbon atoms; Or a b-valent heteroaryl group having 2 to 12 carbon atoms.

In the exemplary embodiment of the present specification, L13 is a substituted or unsubstituted b-valent phenyl group; A substituted or unsubstituted b-valent biphenyl group; b-valent dibenzofuranyl group; Or a b-valent pyridinyl group.

In the exemplary embodiment of the present specification, when L13 is a substituted b-valent aryl group, the substituent of the b-valent aryl group is an aryl group substituted with a heteroaryl group.

In the exemplary embodiment of the present specification, G11 and G12 are the same as or different from each other, and each independently hydrogen; Or a cyano group.

In the exemplary embodiment of the present specification, b13 is 1.

In the exemplary embodiment of the present specification, b13 is 2.

In the exemplary embodiment of the present specification, R43 is a phenyl group.

In the exemplary embodiment of the present specification, L14 is a direct bond; An arylene group unsubstituted or substituted with a heteroaryl group including O or S; Or a heteroarylene group substituted or unsubstituted with a cyano group and containing O, S or N.

In the exemplary embodiment of the present specification, L14 is a direct bond; A phenylene group unsubstituted or substituted with a dibenzofuranyl group or a dibenzothiophenyl group; A biphenylene group unsubstituted or substituted with a dibenzofuranyl group or a dibenzothiophenyl group; A divalent carbazolyl group unsubstituted or substituted with a cyano group; Divalent dibenzofuranyl group; Or a divalent pyridinyl group.

In the exemplary embodiment of the present specification, b14 is an integer of 0 to 2.

In the exemplary embodiment of the present specification, G15 is an aryl group having 6 to 12 carbon atoms.

In the exemplary embodiment of the present specification, G15 is a phenyl group.

In the exemplary embodiment of the present specification, G13 and G14 are the same as or different from each other, and are each independently an aryl group having 6 to 24 carbon atoms.

In the exemplary embodiment of the present specification, G13 and G14 are the same as or different from each other, and are each independently an aryl group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, G13 and G14 are the same as or different from each other, and each independently a biphenyl group; Or terphenyl group.

In the exemplary embodiment of the present specification, L15 and L16 are the same as or different from each other, and each independently a direct bond; An arylene group having 6 to 12 carbon atoms; Or it is a C2-C12 heteroarylene group.

In the exemplary embodiment of the present specification, L15 is a direct bond; Phenylene group; Or it is a naphthylene group.

In the exemplary embodiment of the present specification, L16 is a direct bond; Phenylene group; Biphenylene group; Divalent dibenzofuranyl group; Or a divalent pyridinyl group.

기이다.In the exemplary embodiment of the present specification, G17 is hydrogen; A carbazolyl group unsubstituted or substituted with a cyano group; Dibenzofuranyl group; Triphenylenyl group; or

It is.

In the exemplary embodiment of the present specification, g is 0 or 1.

In the exemplary embodiment of the present specification, L17 is an arylene group having 6 to 24 carbon atoms.

In the exemplary embodiment of the present specification, L17 is an arylene group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, L17 is a phenylene group; Or a biphenylene group.

In the exemplary embodiment of the present specification, G18 is an aryl group having 6 to 18 carbon atoms; Or it is a C2-C18 heteroaryl group.

In the exemplary embodiment of the present specification, G19 is an aryl group having 6 to 18 carbon atoms; Or it is a C2-C18 heteroaryl group.

In the exemplary embodiment of the present specification, L19 is a direct bond; Or an arylene group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, G18 is a phenyl group; Biphenyl group; Terphenyl group; Or a triphenylene group.

In the exemplary embodiment of the present specification, L19 is a direct bond; Phenylene group; Biphenylene group; Or terphenylene group.

In the exemplary embodiment of the present specification, G19 is a phenyl group; Biphenyl group; Dibenzofuranyl group; Or a dibenzothiophenyl group.

In an exemplary embodiment of the present specification, the compound represented by Chemical Formula 31 is represented by the following compound.

In the exemplary embodiment of the present specification, the compound represented by Formula 32 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Formula 33 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Chemical Formula 34 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Formula 35 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Formula 36 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Chemical Formula 37 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Formula 38 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Formula 39 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the light emitting layer including the compound represented by Formula 1 may further include an auxiliary dopant or a sensitizer.

At this time, the auxiliary dopant or the compound acting as a sensitizer receives holes and electrons from the host to form excitons, and the generated excitons are used as a fluorescent dopant. It plays a role of delivering to. As the auxiliary dopant and sensitizer, a known suitable compound may be used in consideration of the energy relationship between the host compound and the compound represented by Formula 1 above.

According to an example, the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. According to another example, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that the organic material layer includes the compound represented by Chemical Formula 1.

For example, the organic light emitting device of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or alloy thereof is deposited on the substrate to form an anode. And, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound of Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate. However, the manufacturing method is not limited thereto.

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

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

The organic light-emitting device may have, for example, a stacked structure as described below, but is not limited thereto.

(1) Anode/Hole Transport Layer/Light-Emitting Layer/Anode

(2) Anode/Hole Injection Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode

(4) Anode/hole transport layer/light-emitting layer/electron transport layer/cathode

(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode

(7) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode

(8) Anode/Hole injection layer/Hole buffer layer/Hole transport layer/Emitting layer/Electron transport layer/Anode

(9) Anode/Hole injection layer/Hole buffer layer/Hole transport layer/Light-emitting layer/Electron transport layer/Electron injection layer/Anode

(10) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode

(11) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode

(12) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode

(13) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode

(14) Anode/Hole transport layer/Light-emitting layer/Hole blocking layer/Electron transport layer/Anode

(15) Anode/Hole transport layer/Light-emitting layer/Hole blocking layer/Electron transport layer/Electron injection layer/Anode

(16) Anode/hole injection layer/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/cathode

(17) Anode/Hole injection layer/Hole transport layer/Light emitting layer/Hole blocking layer/Electron transport layer/Electron injection layer/Anode

For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3.

1 shows an organic light-emitting device comprising a substrate 1, an anode 2, a hole transport layer 6, a light-emitting layer 3, and a cathode 4. In such a structure, the compound of Formula 1 may be included in the emission layer.

2 shows an organic light-emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron transport layer 7 and a cathode 4 . In such a structure, the compound of Formula 1 may be included in the emission layer.

3 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (8), a light emitting layer (3), an electron injection and transport layer (9) and a cathode (4). It shows an organic light emitting device made of. In such a structure, the compound of Formula 1 may be included in the emission layer.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the 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); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes received from an electrode into a light emitting layer or a layer adjacent to the light emitting layer. The hole injection material has the ability to transport holes and thus has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and transfer of excitons generated in the light emitting layer to the electron injection layer or the electron injection material. It is preferable to use a compound that prevents and has excellent thin film formation ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene There are a series of organic substances, anthraquinone, and polyaniline and a polythiophene series of conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to a light emitting layer or an adjacent layer provided toward the light emitting layer. The hole transport material is a material capable of transporting holes from an anode or a hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples of the hole transport material include NPD (N,N-dinaphthyl-N,N'-diphenylbenzidine), TPD (N,N'-bis-(3-methylphenyl)-N,N'-bis-(phenyl)- benzidine), s-TAD and MTDATA(4,4',4"- Tris(N-3-methylphenyl-N-phenyl-amino)-triphenylamine), triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyaryl Alkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, Silasein derivatives, polysilane-based, aniline-based copolymers, conductive polymer oligomers (especially thiophene oligomers), and the like, but are not limited thereto.

A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer. As the hole buffer layer, a hole injection or transport material known in the art may be used.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer, and materials known in the art may be used. The electron blocking layer is a layer that prevents electrons from flowing into the light-emitting layer and controls the flow of holes flowing into the light-emitting layer to control the performance of the entire device. The electron blocking material is preferably a compound having the ability to prevent the inflow of electrons from the emission layer to the anode and to control the flow of holes injected into the emission layer or the emission material. In one embodiment, an arylamine-based organic material may be used as the electron blocking layer, but is not limited thereto.

A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used. The hole blocking layer is a layer that blocks the introduction of holes from the emission layer to the cathode and controls the electrons flowing into the emission layer to control the performance of the entire device. The hole blocking material is preferably a compound having the ability to prevent the inflow of holes from the light emitting layer to the cathode and control electrons injected into the light emitting layer or the light emitting material. As the hole blocking material, an appropriate material may be used according to the configuration of the organic material layer used in the device. The hole blocking layer is located between the emission layer and the cathode, and is preferably provided in direct contact with the emission layer.

The electron transport layer may play a role of facilitating the transport of electrons. Materials known in the art such as Alq ₃ (tris(8-hydroxyquinolino)aluminum), PBD, TAZ, spiro-PBD, BAlq, and SAlq may be used. The thickness of the electron transport layer may be 1 to 50 nm. Here, if the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing deterioration of the electron transport characteristics, and if the thickness of the electron transport layer is 50 nm or less, the thickness of the electron transport layer is too thick and the driving voltage is increased to improve the movement of electrons. There is an advantage that can prevent it.

The electron injection layer may play a role of smoothly injecting electrons. Alq ₃ (tris(8-hydroxyquinolino)aluminum), PBD, TAZ, spiro-PBD, BAlq or SAlq known in the art, such as organic substances or complexes or metal compounds. Organic substances that can be used in the electron injection layer are fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, benzoimidazole, perylenetetracarboxylic acid, preorenyli Den methane, anthrone and the like, derivatives thereof, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, but are not limited thereto. With the metal compound is a metal halide, and cargo may be used, such as LiQ, LiF, may be is used NaF, KF, RbF, CsF, FrF, BeF _2, MgF _2, CaF _2, SrF _2, BaF ₂ and RaF ₂ etc. . The thickness of the electron injection layer may be 1 to 50 nm. Here, when the thickness of the electron injection layer is 1 nm or more, there is an advantage of preventing deterioration of the electron injection characteristics, and when the thickness of the electron injection layer is 50 nm or less, the thickness of the electron injection layer is too thick to increase the driving voltage to improve the movement of electrons. There is an advantage that can prevent it from rising. In an exemplary embodiment, the electron injection layer may be formed by mixing the organic material and the metal compound.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto. The cathode may be formed to have a thickness thin enough to transmit light when the organic light emitting device has a front or double-sided light emitting structure, and when the organic light emitting device has a rear light emitting structure, the cathode may be formed thick enough to reflect light I can.

One or more organic material layers such as the above-described hole injection layer, hole buffer layer, hole transport layer, electron blocking layer, hole blocking layer, electron transport layer, and electron injection layer are further formed between the emission layer and the anode or the cathode, and between the emission layer and the charge generation layer. Can be included.

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

<Production Example>

The compound represented by Formula 1 can be prepared from the process of forming a ring by introducing (4-chloro-2-hydroxyphenyl) boronic acid to halide-substituted naphthalene as follows. The compounds of the specific examples were synthesized step by step through the following process.

Preparation Example 1-1: Synthesis of Compound 1-A

(4-chloro-2-hydroxyphenyl) boronic acid 30g (174mmol), 2,6-dibromo-1,5-difluoronaphthalene 87mmol, tetrahydrofuran 200mL and water 100mL were mixed and heated to 60℃ I did. Potassium carbonate (522 mmol) and tetrakistriphenylphosphine palladium (1.7 mmol) were added, and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to obtain 32.6 g of compound 1-A (yield 90%).

MS[M+H] ⁺ = 417

Preparation Example 1-2: Synthesis of Compound 1-B

(4-chloro-2-hydroxyphenyl) boronic acid 30g (174mmol), 1,5-dibromo-2,6-difluoronaphthalene 87mmol, tetrahydrofuran 200mL and water 100mL were mixed and heated to 60℃ I did. Potassium carbonate (522 mmol) and tetrakistriphenylphosphine palladium (1.7 mmol) were added, and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to obtain 31.6 g of compound 1-B (yield 87%).

MS[M+H] ⁺ = 417

Preparation Example 1-3: Synthesis of Compound 1-C

(4-chloro-2-hydroxyphenyl) boronic acid 30g (174mmol), 2,6-dibromo-3,7-difluoronaphthalene 87mmol, tetrahydrofuran 200mL and water 100mL mixed and heated to 60 ℃ I did. Potassium carbonate (522 mmol) and tetrakistriphenylphosphine palladium (1.7 mmol) were added, and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to give 31.9 g of compound 1-C (yield 88%).

MS[M+H] ⁺ = 417

Preparation Example 2-1: Synthesis of Compound 2-A

Compound 1-A 25g (59.9mmol), potassium carbonate 240mmol, dimethylformamide 300mL were mixed, heated at 60° C. for 1 hour, and stirred for 1 hour in reflux state. After the reaction, the reaction solution returned to room temperature was reverse-precipitated in water to obtain a solid, and then recrystallized twice with tetrahydrofuran and ethanol to obtain 18.5 g of compound 2-A (yield 82%).

MS[M+H] ⁺ = 377

Preparation Example 2-2: Synthesis of Compound 2-B

Compound 1-B 25g (59.9mmol), potassium carbonate 240mmol, dimethylformamide 300mL were mixed, heated at 60° C. for 1 hour, and stirred for 1 hour in reflux state. After the reaction, the reaction solution returned to room temperature was reverse-precipitated in water to obtain a solid, and then recrystallized twice with tetrahydrofuran and ethanol to obtain 18.1 g of compound 2-B (yield 80%).

MS[M+H] ⁺ = 377

Preparation Example 2-3: Synthesis of Compound 2-C

Compound 1-C 25g (59.9mmol), potassium carbonate 240mmol, dimethylformamide 300mL were mixed, heated at 60°C for 1 hour, and stirred for 1 hour in reflux state. After the reaction, the reaction solution returned to room temperature was reverse-precipitated in water to obtain a solid, and then recrystallized twice with tetrahydrofuran and ethanol to obtain 19.2 g of compound 2-C (yield 85%).

MS[M+H] ⁺ = 377

Preparation Example 3-1: Synthesis of Compound 3-A

Compound 2-A 18.8 g (50 mmol) and 450 mL of dimethylformamide were mixed, and N-bromosuccinimide (NBS) 100 mmol was added at 0° C., followed by stirring at room temperature for 1 hour. After the reaction, the reaction solution was reverse-precipitated in water to obtain a solid, and then recrystallized twice with tetrahydrofuran and ethanol to obtain 22.7 g of compound 3-A (yield 85%).

MS[M+H] ⁺ = 535

Preparation Example 3-2: Synthesis of Compound 3-B

In a nitrogen atmosphere, 200 ml of tetrahydrofuran was added to 18.8 g (50 mmol) of compound 2-B, and 100 mmol of n-butyllithium was added at -78°C. After stirring at -78°C for 2 hours, 100 mmol of bromine was added at -78°C, followed by stirring for 30 minutes. After the reaction, the reaction solution was reverse-precipitated in an aqueous sodium thiosulfate solution to obtain a solid, and then recrystallized twice with tetrahydrofuran and ethanol to obtain 21.7 g of compound 3-B (yield 81%).

MS[M+H] ⁺ = 535

Preparation Example 3-3: Synthesis of Compound 3-C

In a nitrogen atmosphere, 200 ml of tetrahydrofuran was added to 18.8 g (50 mmol) of compound 2-C, and 100 mmol of n-butyllithium was added at -78°C. After stirring at -78°C for 2 hours, 100 mmol of bromine was added at -78°C, followed by stirring for 30 minutes. After the reaction, the reaction solution was reverse-precipitated in an aqueous sodium thiosulfate solution to obtain a solid, and then recrystallized twice with tetrahydrofuran and ethanol to obtain 21.1 g of compound 3-C (yield 79%).

MS[M+H] ⁺ = 535

Synthesis of compound 1

Compound 3-A 10.7 g (20 mmol), sodium-t-butoxide 100 mmol, diphenylamine 80 mmol and toluene 200 mL were mixed, refluxed, heated for 30 minutes, and tetrakistriphenylphosphine palladium 0.2 mmol was added to reflux. The mixture was stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 16.2 g of compound 1 (yield 83%).

MS[M+H] ⁺ = 977

Synthesis of compound 2

Compound 3-A 10.7g (20mmol), phenanthrene-9-ylboronic acid 40mmol, tetrahydrofuran 200mL, and water 100mL were mixed and heated to 60 ℃. Potassium carbonate (120 mmol) and tetrakistriphenylphosphine palladium (0.2 mmol) were added, followed by stirring for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and recrystallized twice with chloroform and hexane to obtain 11.7 g of compound 4-A (yield 80%).

MS[M+H] ⁺ = 729

Compound 4-A 10.9 g (15 mmol), sodium-t-butoxide 37.5 mmol, diphenylamine 30 mmol, and toluene 100 mL were mixed, refluxed, heated for 30 minutes, and tetrakistriphenylphosphine palladium 0.2 mmol was added to reflux. The mixture was stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 11.9 g of compound 2 (yield 80%).

MS[M+H] ⁺ = 995

Synthesis of compound 3

Compound 3-A 10.7g (20mmol), sodium-t-butoxide 100mmol, di-p-tolylamine 40mmol and toluene 200mL were mixed, refluxed and heated for 30 minutes, and tetrakistriphenylphosphine palladium 0.2mmol was added. The mixture was stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 12.7 g of compound 4-B (yield 83%).

MS[M+H] ⁺ = 767

Compound 4-B 11.5 g (15 mmol), 4-t-butylphenylboronic acid 30 mmol, 1,4-dioxane 100 mL, and water 50 mL were mixed and heated to 60°C. Potassium phosphate (90 mmol) and tetrakistriphenylphosphine palladium (0.2 mmol) were added, followed by stirring in a reflux state for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to obtain 8.8 g of compound 3 (yield 61%).

MS[M+H] ⁺ = 963

Synthesis of compound 4

Compound 3-B 10.7g (20mmol), sodium-t-butoxide 100mmol, diphenylamine 80mmol and toluene 200mL were mixed, refluxed, heated for 30 minutes, tetrakistriphenylphosphine palladium 0.2mmol was added to reflux state And stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to give 15.2 g of compound 4 (yield 78%).

MS[M+H] ⁺ = 977

Synthesis of compound 5

Compound 3-B 10.7 g (20 mmol), phenanthrene-9-ylboronic acid 40 mmol, tetrahydrofuran 200 mL, and water 100 mL were mixed and heated to 60°C. Potassium carbonate (120 mmol) and tetrakistriphenylphosphine palladium (0.2 mmol) were added, and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to obtain 12.3 g of compound 4-C (yield 84%).

MS[M+H] ⁺ = 729

Compound 4-C 10.9 g (15 mmol), sodium-t-butoxide 37.5 mmol, diphenylamine 30 mmol, and toluene 100 mL were mixed, refluxed, heated for 30 minutes, and tetrakistriphenylphosphine palladium 0.2 mmol was added to reflux. The mixture was stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to give 12.2 g of compound 5 (yield 82%).

MS[M+H] ⁺ = 995

Synthesis of compound 6

Compound 3-B 10.7 g (20 mmol), sodium-t-butoxide 100 mmol, di-p-tolylamine 40 mmol, and toluene 200 mL were mixed, refluxed, heated for 30 minutes, and tetrakistriphenylphosphine palladium 0.2 mmol was added. The mixture was stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 12.4 g of compound 4-D (yield 81%).

MS[M+H] ⁺ = 767

Compound 4-D 11.5g (15mmol), 4-t-butylphenylboronic acid 30mmol, 1,4-dioxane 100mL and water 50mL were mixed and heated to 60 ℃. Potassium phosphate (90 mmol) and tetrakistriphenylphosphine palladium (0.2 mmol) were added, followed by stirring in a reflux state for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to obtain 9.1 g of compound 6 (yield 63%).

MS[M+H] ⁺ = 963

Synthesis of compound 7

Compound 3-C 10.7g (20mmol), sodium-t-butoxide 100mmol, diphenylamine 80mmol and toluene 200mL were mixed, refluxed, heated for 30 minutes, tetrakistriphenylphosphine palladium 0.2mmol was added to reflux And stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to give 14.6 g of compound 7 (yield 75%).

MS[M+H] ⁺ = 977

Synthesis of compound 8

Compound 3-C 10.7g (20mmol), phenanthrene-9-ylboronic acid 40mmol, tetrahydrofuran 200mL and water 100mL were mixed and heated to 60 ℃. Potassium carbonate (120 mmol) and tetrakistriphenylphosphine palladium (0.2 mmol) were added, followed by stirring for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to obtain 11.8 g of compound 4-E (yield 81%).

MS[M+H] ⁺ = 729

Compound 4-E 10.9 g (15 mmol), sodium-t-butoxide 37.5 mmol, diphenylamine 30 mmol, and toluene 100 mL were mixed, refluxed, heated for 30 minutes, and tetrakistriphenylphosphine palladium 0.2 mmol was added to reflux. The mixture was stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 11.9 g of compound 8 (yield 80%).

MS[M+H] ⁺ = 995

Synthesis of compound 9

Compound 3-C 10.7 g (20 mmol), sodium-t-butoxide 100 mmol, di-p-tolylamine 40 mmol and toluene 200 mL were mixed, refluxed, heated for 30 minutes, and tetrakistriphenylphosphine palladium 0.2 mmol was added. The mixture was stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 12.7 g of compound 4-F (yield 83%).

MS[M+H] ⁺ = 767

11.5 g (15 mmol) of 4-F, 30 mmol of 4-t-butylphenylboronic acid, 100 mL of 1,4-dioxane, and 50 mL of water were mixed and heated to 60°C. Potassium phosphate (90 mmol) and tetrakistriphenylphosphine palladium (0.2 mmol) were added, followed by stirring in a reflux state for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to obtain 8.5 g of compound 9 (yield 59%).

MS[M+H] ⁺ = 963

Synthesis of compound 10

Compound 3-B 10.7 g (20 mmol), sodium-t-butoxide 100 mmol, 10,11-dihydro-5H-dibenzo[b,f] azepine 40 mmol and toluene 200 mL were mixed, refluxed and heated for 30 minutes. Tetrakistriphenylphosphine palladium 0.2 mmol was added, and the mixture was stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 12.2 g of compound 4-G (yield 80%).

MS[M+H] ⁺ = 763

Compound 4-G 11.5g (15mmol), sodium-t-butoxide 37.5mmol, diphenylamine 30mmol and toluene 100mL were mixed, refluxed, heated for 30 minutes, tetrakistriphenylphosphine palladium 0.2mmol was added to reflux The mixture was stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to give 12.8 g of compound 10 (yield 83%).

MS[M+H] ⁺ = 1029

Synthesis of compound 11

Compound 3-B 10.7 g (20 mmol), sodium-t-butoxide 100 mmol, 9-H-carbazole 40 mmol and toluene 200 mL were mixed, refluxed, heated for 30 minutes, and tetrakistriphenylphosphine palladium 0.2 mmol was added. The mixture was stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 12 g of compound 4-H (yield 85%).

MS[M+H] ⁺ = 707

Compound 4-H 10.6g (15mmol), sodium-t-butoxide 37.5mmol, diphenylamine 30mmol and toluene 100mL were mixed, refluxed, heated for 30 minutes, and tetrakistriphenylphosphine palladium 0.2mmol was added to reflux. The mixture was stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to give 11.8 g of compound 11 (yield 81%).

MS[M+H] ⁺ = 973

Synthesis of compound 12

Compound 3-A 10.7g (20mmol), sodium-t-butoxide 100mmol, 10H-phenoxazine 40mmol and toluene 200mL were mixed, refluxed and heated for 30 minutes, and tetrakistriphenylphosphine palladium 0.2mmol was added to reflux. The mixture was stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 11.8 g of compound 4-K (yield 80%).

MS[M+H] ⁺ = 739

Compound 4-K 11.1g (15mmol), sodium-t-butoxide 37.5mmol, 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine 30mmol and toluene 100mL were mixed and refluxed for 30 minutes After heating, 0.2 mmol of tetrakistriphenylphosphine palladium was added, and the mixture was stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to give 14.5 g of compound 12 (yield 78%).

MS[M+H] ⁺ = 1237

Synthesis of compound 13

Compound 3-B 10.7g (20mmol), sodium-t-butoxide 100mmol, 10H-spiro[acridine-9,9'-fluorene] 40mmol and toluene 200mL were mixed, refluxed, heated for 30 minutes, and tetra 0.2 mmol of kisstriphenylphosphine palladium was added, and the mixture was stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 16.4 g of compound 4-I (yield 79%).

MS[M+H] ⁺ = 1035

Compound 4-I 15.5g (15mmol), sodium-t-butoxide 37.5mmol, bis(4-(tert-butyl)phenyl)amine 30mmol and toluene 100mL were mixed, refluxed, heated for 30 minutes, and tetrakistriphenylphos 0.2 mmol of fin palladium was added and the mixture was stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 17.2 g of compound 13 (yield 75%).

MS[M+H] ⁺ = 1525

Synthesis of compound 14

Compound 3-A 10.7g (20mmol), sodium-t-butoxide 100mmol, di(naphthalen-2-yl)amine 40mmol and toluene 200mL were mixed, refluxed, heated for 30 minutes, tetrakistriphenylphosphine palladium 0.2mmol Was added and stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 13.3 g of compound 4-L (yield 73%).

MS[M+H] ⁺ = 911

Compound 4-L 13.7 g (15 mmol), sodium-t-butoxide 37.5 mmol, N-phenyl-[1,1'-biphenyl]-4-amine 30 mmol and toluene 100 mL were mixed, refluxed and heated for 30 minutes. Tetrakistriphenylphosphine palladium 0.2 mmol was added, and the mixture was stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to give 15.7 g of compound 14 (yield 79%).

MS[M+H] ⁺ = 1329

Synthesis of compound 15

Compound 3-A 10.7g (20mmol), sodium-t-butoxide 100mmol, N-phenyldibenzo[b,d]thiophen-2-amine 40mmol and toluene 200mL were mixed, refluxed, heated for 30 minutes, and tetrakis Triphenylphosphine palladium 0.2mmol was added, and the mixture was stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 14 g of compound 4-M (yield 76%).

MS[M+H] ⁺ = 923

Compound 4-M 13.8 g (15 mmol), sodium-t-butoxide 37.5 mmol, 4-methyl-N-phenylaniline 30 mmol and toluene 100 mL were mixed, refluxed, heated for 30 minutes, tetrakistriphenylphosphine palladium 0.2 mmol Was added and stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 15 g of compound 15 (yield 82%).

MS[M+H] ⁺ = 1217

Synthesis of compound 16

Compound 3-A 10.7g (20mmol), sodium-t-butoxide 100mmol, 2-(phenylamino)benzonitrile 40mmol and toluene 200mL were mixed, refluxed, heated for 30 minutes, tetrakistriphenylphosphine palladium 0.2mmol Was added and stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 11.9 g of compound 4-N (yield 78%).

MS[M+H] ⁺ = 761

Compound 4-N 11.4g (15mmol), sodium-t-butoxide 37.5mmol, N-phenyl-[1,1'-biphenyl]-4-amine 30mmol and toluene 100mL were mixed, refluxed and heated for 30 minutes. Tetrakistriphenylphosphine palladium 0.2 mmol was added, and the mixture was stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to give 14.1 g of compound 16 (yield 80%).

MS[M+H] ⁺ = 1179

Synthesis of compound 17

Compound 3-B 10.7 g (20 mmol), sodium-t-butoxide 100 mmol, bis (4-fluorophenyl) amine 40 mmol and toluene 200 mL were mixed, refluxed, heated for 30 minutes, tetrakistriphenylphosphine palladium 0.2 mmol Was added and stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 12.1 g of compound 4-J (yield 77%).

MS[M+H] ⁺ = 783

Compound 4-J 11.7 g (15 mmol), sodium-t-butoxide 37.5 mmol, 4-methyl-N-phenylaniline 30 mmol and toluene 100 mL were mixed, refluxed, heated for 30 minutes, tetrakistriphenylphosphine palladium 0.2 mmol Was added and stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to give 13.4 g of compound 17 (yield 83%).

MS[M+H] ⁺ = 1077

Synthesis of compound 18

Compound 3-A 10.7g (20mmol), sodium-t-butoxide 100mmol, 4-methoxy-N-phenylaniline 40mmol and toluene 200mL were mixed, refluxed, heated for 30 minutes, tetrakistriphenylphosphine palladium 0.2mmol Was added and stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 11.1 g of compound 4-O (yield 72%).

MS[M+H] ⁺ = 771

Compound 4-O 11.6 g (15 mmol), sodium-t-butoxide 37.5 mmol, 4-methyl-N-phenylaniline 30 mmol and toluene 100 mL were mixed, refluxed, heated for 30 minutes, tetrakistriphenylphosphine palladium 0.2 mmol Was added and stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to give 12.9 g of compound 18 (yield 81%).

MS[M+H] ⁺ = 1065

Synthesis of compound 19

Compound 3-A 10.7g (20mmol), sodium-t-butoxide 100mmol, 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine 40mmol and toluene 200mL were mixed, refluxed and heated for 30 minutes Then, 0.2 mmol of tetrakistriphenylphosphine palladium was added, and the mixture was stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 13.2 g of compound 4-P (yield 70%).

MS[M+H] ⁺ = 943

Compound 4-P 14.1 g (15 mmol), sodium-t-butoxide 37.5 mmol, 10,11-dihydro-5H-dibenzo[b,f] azepine 30 mmol and toluene 100 mL were mixed, refluxed and heated for 30 minutes Then, 0.2 mmol of tetrakistriphenylphosphine palladium was added, and the mixture was stirred for 3 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was recrystallized twice with chloroform to give 14.6 g of compound 19 (yield 77%).

MS[M+H] ⁺ = 1261

By using the same reaction as in the above scheme, various types of substituents may be introduced to synthesize the materials of the specific examples.

An organic light-emitting device was manufactured by including Formula 1 according to an exemplary embodiment of the present specification in the emission layer, and characteristics were evaluated.

In this experimental example, the host material (m-CBP) having a triplet energy of 2.9 eV with Formula 1 according to an exemplary embodiment of the present specification, ΔE _ST (difference between singlet energy and triplet energy) is 0.3 eV A green organic light-emitting device was manufactured by including a Sensitizer (4CzIPN) having the following TADF (delayed fluorescence) characteristics in the emission layer, and the characteristics were evaluated.

<Comparative Example 1>

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator. Each thin film was stacked on the thus prepared ITO transparent electrode by vacuum evaporation with a vacuum degree of 5.0 占10 ^-4 Pa. First, hexanitrilehexaazatriphenylene (HAT-CN) was thermally vacuum deposited to a thickness of 500Å on ITO to form a hole injection layer.

The following compound 4-4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (300Å) was vacuum deposited on the hole injection layer to form a hole transport layer.

Compound N-([1,1'-bisphenyl]-4-yl)-N-(4-(11-([1,1'-biphenyl]-4-yl) with a film thickness of 100Å on the hole transport layer )-11H-benzo[a]carbazole-5-yl)phenyl)-[1,1'-biphenyl]-4-amine (EB1) (100Å) was vacuum deposited to form an electron blocking layer.

Subsequently, m-CBP, 4CzIPN, and GD1 were vacuum-deposited on the electron blocking layer at a weight ratio of 69:30:1 with a thickness of 300Å as follows to form a light emitting layer.

An electron injection and transport layer was formed with a thickness of 300Å by vacuum depositing compound ET1 and compound LiQ (Lithium Quinolate) at a weight ratio of 1:1 on the emission layer. Lithium fluoride (LiF) in a thickness of 12 Å and aluminum in a thickness of 2,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 0.4 Å/sec to 0.7 Å/sec, the deposition rate of lithium fluoride of the negative electrode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec. ×10 ^-7 torr to 5 × 10 ^-6 torr was maintained.

<Experimental Examples 1-1 to 1-19>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound of Table 1 below was used instead of the compound GD1 in Comparative Example 1.

<Comparative Examples 2 to 4>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound of GD2, GD3, or GD4 was used instead of the compound GD1 in Comparative Example 1.

When a current was applied to the organic light emitting devices manufactured according to Experimental Examples 1-1 to 1-19 and Comparative Examples 1 to 4, the results of measuring voltage, efficiency and color coordinates (CIE) are shown in Table 1 below.

division compound
(Luminescent layer) Voltage
(V@10mA/cm ² ) efficiency
(cd/A@10mA/cm ² ) Color coordinates
(x,y) Experimental Example 1 One 4.1 22 (0.22, 0.67) Experimental Example 2 2 4.0 21 (0.23, 0.66) Experimental Example 3 3 3.9 21 (0.23, 0.67) Experimental Example 4 4 4.1 20 (0.22, 0.68) Experimental Example 5 5 3.9 22 (0.24, 0.67) Experimental Example 6 6 4.0 20 (0.23, 0.66) Experimental Example 7 7 4.1 21 (0.24, 0.66) Experimental Example 8 8 3.9 21 (0.23, 0.67) Experimental Example 9 9 4.0 20 (0.24, 0.67) Experimental Example 10 10 4.0 21 (0.23, 0.67) Experimental Example 11 11 3.9 21 (0.22, 0.67) Experimental Example 12 12 4.1 20 (0.23, 0.66) Experimental Example 13 13 4.0 20 (0.22, 0.68) Experimental Example 14 14 4.0 19 (0.23, 0.67) Experimental Example 15 15 4.1 19 (0.24, 0.67) Experimental Example 16 16 4.1 20 (0.23, 0.66) Experimental Example 17 17 4.2 18 (0.24, 0.66) Experimental Example 18 18 4.0 21 (0.22, 0.67) Experimental Example 19 19 4.0 21 (0.23, 0.66) Comparative Example 1 GD1 4.5 13 (0.30, 0.61) Comparative Example 2 GD2 4.3 10 (0.21, 0.41) Comparative Example 3 GD3 4.3 11 (0.22, 0.43) Comparative Example 4 GD4 4.8 8 (0.22, 0.33)

As shown in Table 1, the devices of Experimental Examples 1-1 to 1-19 using the compound having the structure of Formula 1 as a core have lower voltage and higher efficiency than the device using the compound GD1 in Comparative Example 1. I got the result.

In addition, when comparing the devices of Comparative Examples 2 to 4, it was found that the structure of Formula 1 of the present application has improved characteristics in terms of voltage and efficiency.

As shown in the results of Table 1, it was confirmed that the compound according to the present invention has excellent light-emitting ability and enables tuning of the light-emitting wavelength, so that the organic light-emitting device of high color purity can be implemented.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: electron transport layer
8: electron blocking layer
9: electron injection and transport layer

Claims (6)

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

In Formula 1,
R1 and R2 are the same as or different from each other, and each independently of a phenanthrenyl group, -N(R5)(R6), -N(R7)(R8), -N(R9)(R10) or the following formulas HAr1 to HAr5 Which one is

In the HAr1 to HAr5,
R21 to R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Alkoxy group; Alkyl group; Or an aryl group,
R33 and R34 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl group; Or an aryl group, R33 and R34 are each a phenyl group and are bonded to each other to deuterium; Halogen group; Cyano group; Alkoxy group; Alkyl group; Or to form a substituted or unsubstituted fluorene ring with an aryl group,
a21 to a28, a31 and a32 are the same as or different from each other, and each independently an integer of 0 to 4,
If a21 is 2 or more, R21 is the same or different, if a22 is 2 or more, R22 is the same or different, and if a23 is 2 or more, R23 is the same or different, and if a24 is 2 or more, R24 is the same or different. And, if a25 is 2 or more, R25 is the same as or different from each other, if a26 is 2 or more, R26 is the same or different, and if a27 is 2 or more, R27 is the same or different, and if a28 is 2 or more, R28 is the same. Or different, and if a31 is 2 or more, R31 is the same as or different from each other, and if a32 is 2 or more, R32 is the same or different from each other,
R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, -N(R11)(R12), -N(R13)(R14), -N(R15)(R16) or substituted or It is an unsubstituted N-containing heterocyclic group,
R5 to R7 and R11 to R13 are the same as or different from each other, and each independently a cyano group, a halogen group, an alkoxy group, or an aryl group unsubstituted or substituted with an alkyl group,
R8 to R10 and R14 to R16 are the same as or different from each other, and each independently a heteroaryl group,
a is 1 or 2, b is 1 or 2, c is an integer from 1 to 4, d is an integer from 1 to 4,
If a is 2, R1 is the same or different from each other, if b is 2, R2 is the same or different from each other, if c is 2 or more, R3 is the same or different from each other, and if d is 2 or more, R4 is the same or different from each other. The compound of claim 1, wherein Formula 1 is represented by any one of the following Formulas 2 to 4:
[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,
The definitions of R1 to R4 and a to d are the same as in Formula 1. delete The compound of claim 1, wherein the compound represented by Formula 1 is any one selected from the following structures:

. An organic light-emitting device comprising a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode, wherein the organic material layer is a compound according to any one of claims 1, 2 and 4 Organic light-emitting device comprising a. The method of claim 5,
The organic material layer includes an emission layer,
The emission layer includes a dopant,
The dopant is an organic light-emitting device, characterized in that the compound.

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