KR102184859B1 - 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

Compound and organic light-emitting device comprising the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

The present invention provides a compound represented by 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. 10-2018-0054968 filed with the Korean Intellectual Property Office on May 14, 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 has a multilayer structure made of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of 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 to the ground.

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

Korean Patent Application Publication No. 10-2004-0049038

The present specification intends to provide an organic light-emitting device having high luminous efficiency or good lifespan characteristics by including the compound represented by Formula 1 in an organic light-emitting device.

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

[Formula 1]

In Formula 1,

L1 and L2 are the same as or different from each other, and each independently a linear or branched chain alkylene group,

Y1 and Y2 are the same as or different from each other, and each independently a cycloalkyl group; Heterocyclic ketone group; Carbocyclic ketone group; Monocyclic or polycyclic aliphatic hydrocarbon ring groups; Monocyclic or polycyclic aryl groups; Monocyclic or polycyclic aliphatic heterocyclic group; Or a monocyclic or polycyclic aromatic heterocyclic group,

R1, R2, Rx, Ry and Rz are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Alkyl group; Alkenyl group; Alkynyl group; Aryl group; Or a heterocyclic group,

n1 is an integer from 0 to 6, and when n1 is 2 or more, a plurality of -(L1-Y1) are the same as or different from each other,

n2 is an integer from 0 to 4, and when n2 is 2 or more, a plurality of -(L2-Y2) are the same or different from each other,

the sum of n1 and n2 is 1 or more,

a is an integer of 0 to 6, and when a is 2 or more, a plurality of R1s are the same as or different from each other,

b is an integer of 0 to 4, and when b is 2 or more, a plurality of R2s are the same or different from each other.

An exemplary embodiment of the present specification is an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the compound represented by Formula 1 is 1 It provides an organic light-emitting device that is included in one or more of the organic material layers of the layer or more.

In an exemplary embodiment of the present invention, when the organic material layer of the organic light-emitting device, particularly the light-emitting layer, includes a compound represented by Formula 1, the efficiency of the device may be improved or the lifespan characteristics of the device may be improved.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.
2 shows a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, a light emitting layer 8, an electron transport layer 9, and an electron injection layer. An example of an organic light-emitting device comprising (10) and a cathode (4) is shown.
3 is a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, a light emitting layer 8, an electron injection and transport layer 11 and a cathode. It shows an example of the organic light-emitting device of (4).

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

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

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification,

Means a site bonded to another substituent or a bonding portion.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent. The position at which the substituent is substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position at which the substituent can be substituted. When the above substituents are 2 or more, the 2 or more substituents may be the same or different from each other.

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

In the present specification, the chain alkylene group refers to a linear or branched divalent chain saturated hydrocarbon. The straight chain alkylene group may be methylene, ethylene, propylene, or the like, but is not limited thereto. The branched chain alkylene group may be dimethylmethylene, 1-methylethylene, 2-methylethylene, 1,1-dimethylethylene, or the like, but is not limited thereto.

In the present specification, an alkyl group refers to a linear or branched saturated hydrocarbon. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 to 20. According to an exemplary embodiment, the alkyl group has 1 to 15 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. The alkyl group may be chain or cyclic.

Specific examples of the chain alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, n-pentyl, isopentyl , Neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc. Not limited.

The number of carbon atoms of the cyclic alkyl group (cycloalkyl group) is not particularly limited, but is preferably 3 to 20 carbon atoms. According to an exemplary embodiment, the cycloalkyl group has 3 to 16 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 12 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 8 carbon atoms. Specific examples of the cycloalkyl group include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like.

In the present specification, the alkenyl group represents a hydrocarbon group having a carbon-carbon double bond, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. Specific examples of the alkenyl group include ethenyl, vinyl, propenyl, allyl, isopropenyl, butenyl, isobutenyl, n-pentenyl and n-hexenyl, but are not limited thereto.

In the present specification, the alkynyl group represents a hydrocarbon group having a carbon-carbon triple bond, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. According to an exemplary embodiment, the number of carbon atoms in the alkynyl group is 2 to 20. Specific examples of the alkynyl group include, but are not limited to, metaynyl, ethynyl, 2-propynyl, 2-butynyl, 1-methyl-2-butynyl, 2-pentynyl, and the like.

In the present specification, the silyl group may be represented by the formula of -SiR ₁₁ R ₁₂ R ₁₃ , wherein R ₁₁ to R ₁₃ are each independently hydrogen; Alkyl group; Or it may be an aryl group. In the present specification, an alkylsilyl group refers to a silyl group substituted with an alkyl group, and an arylsilyl group refers to a silyl group substituted with an aryl group. The silyl group may specifically be trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but is not limited thereto.

In the present specification, the aliphatic hydrocarbon ring group means a monovalent aliphatic hydrocarbon ring. The aliphatic hydrocarbon ring is a ring that is not aromatic and refers to a ring consisting only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, It is not limited to this.

In the present specification, an aryl group means a monocyclic or polycyclic aromatic hydrocarbon ring consisting only of carbon and hydrogen atoms. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. Examples of the monocyclic aryl group include phenyl, biphenyl, and terphenyl, but are not limited thereto. Examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthrenyl, perylenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetracenyl, chrysenyl, pentacenyl, fluorenyl, indenyl, Acenaphthyl, benzofluorenyl, spirofluorenyl, and the like, but are 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.

,

,

,

,

,

,

및

등이 있으나, 이에 한정되지 않는다.The substituted fluorenyl group is

,

,

,

,

,

,

And

And the like, but are not limited thereto.

In the present specification, the heterocyclic group is a ring having two or more elements constituting the ring. The heterocyclic group includes an aliphatic heterocyclic group and an aromatic heterocyclic group.

In the present specification, the aliphatic heterocyclic group means a monovalent aliphatic heterocycle. The aliphatic heterocycle means an aliphatic ring in which at least one of the heteroatoms is included in an atom constituting the ring. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, pyrrolidine-2,5-dione, piperidine, Morpholine, oxephan, azocaine, thiocane, and the like, but are not limited thereto.

In the present specification, the aromatic heterocyclic group means a monovalent aromatic heterocycle. The aromatic heterocycle means an aromatic ring in which at least one of the heteroatoms is included in an atom constituting the ring. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, Acridine, phenanthridine, diazanaphthalene, dryazainden, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carba Sol, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, phenanthridine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

In the present specification, the heterocyclic ketone group means a monovalent heterocyclic ketone. The heterocyclic ketone means a cyclic ketone in which at least two or more different atoms are present in an atom constituting the ring. The heterocyclic ketone is, for example, pyrrolidone, pyrrolidine-2,5-dione, benzofuran-2[3H]-one, 3a,6,7,7a-tetrahydrobenzofuran-2[ 3H]-one, 1H-isochromen-1-one, 5-pentanolide, and the like, but are not limited thereto.

In the present specification, a carbocyclic ketone group means a monovalent carbocyclic ketone. The carbocyclic ketone means a cyclic ketone in which a ring member is composed of only carbon atoms. The carbocyclic ketone may be, for example, cyclopentanone, cyclohexanone, or the like, but is not limited thereto.

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

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a linear or branched chain alkylene group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a linear or branched chain alkylene group having 1 to 8 carbon atoms.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a linear or branched chain alkylene group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a linear or branched chain alkylene group having 1 to 5 carbon atoms.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a linear chain alkylene group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a straight chain alkylene group having 1 to 5 carbon atoms.

In the exemplary embodiment of the present specification, L1 and L2 are each methylene.

In the exemplary embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently a cycloalkyl group; Heterocyclic ketone group; Carbocyclic ketone group; Monocyclic or polycyclic aliphatic hydrocarbon ring groups; Monocyclic or polycyclic aryl groups; A monocyclic or polycyclic aliphatic heterocyclic group containing at least one of O, N and S; Or a monocyclic or polycyclic aromatic heterocyclic group containing at least one of O, N and S.

In the exemplary embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently a cycloalkyl group; A heterocyclic ketone group including N; Carbocyclic ketone group; Monocyclic or polycyclic aliphatic hydrocarbon ring groups; Monocyclic or polycyclic aryl groups; A monocyclic or polycyclic aliphatic heterocyclic group including O or S; Or a monocyclic or polycyclic aromatic heterocyclic group containing O or S.

In the exemplary embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently a cycloalkyl group having 3 to 8 carbon atoms; A heterocyclic ketone group having 2 to 12 carbon atoms; A carbocyclic ketone group having 4 to 14 carbon atoms; Monocyclic or polycyclic aliphatic hydrocarbon ring groups having 3 to 15 carbon atoms; Monocyclic or polycyclic aryl groups having 6 to 25 carbon atoms; A monocyclic or polycyclic aliphatic heterocyclic group having 2 to 20 carbon atoms; Or a monocyclic or polycyclic aromatic heterocyclic group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently a cycloalkyl group having 3 to 6 carbon atoms; A heterocyclic ketone group having 2 to 10 carbon atoms; A carbocyclic ketone group having 4 to 12 carbon atoms; Monocyclic or polycyclic aliphatic hydrocarbon ring groups having 3 to 12 carbon atoms; Monocyclic or polycyclic aryl group having 6 to 18 carbon atoms; A monocyclic or polycyclic aliphatic heterocyclic group having 2 to 16 carbon atoms; Or a monocyclic or polycyclic aromatic heterocyclic group having 2 to 16 carbon atoms.

In the exemplary embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently a cycloalkyl group having 3 to 6 carbon atoms; A heterocyclic ketone group having 2 to 8 carbon atoms; A carbocyclic ketone group having 4 to 9 carbon atoms; Monocyclic or polycyclic aliphatic hydrocarbon ring groups having 3 to 8 carbon atoms; Monocyclic or polycyclic aryl group having 6 to 15 carbon atoms; A monocyclic or polycyclic aliphatic heterocyclic group having 2 to 12 carbon atoms; Or a monocyclic or polycyclic aromatic heterocyclic group having 2 to 12 carbon atoms.

In the exemplary embodiment of the present specification, Y1 and Y2 are the same as or different from each other, each independently consisting of an element selected from the group consisting of N, O, S, and C, and a 5- or 6-membered aliphatic or aromatic ring group; Or a 5-membered cycloketone group consisting of an element selected from the group consisting of N and C.

In the exemplary embodiment of the present specification, Y1 and Y2 are the same or different from each other, each independently consisting of an element selected from the group consisting of N, O, S, and C, and is a 5- or 6-membered aliphatic or aromatic ring group. .

In the exemplary embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently cyclopentyl; Cyclohexyl; Phenyl; Oxacyclopentyl; Oxacyclohexyl; Furanyl; Thiophenyl; Pyrrole-2,5-dionyl; Or pyrrolidine-2,5-dionyl.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently deuterium; Or an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently deuterium; Or an alkyl group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently deuterium; Or it is a C1-C3 alkyl group.

In the exemplary embodiment of the present specification, R1 is hydrogen.

In the exemplary embodiment of the present specification, R2 is hydrogen.

In the exemplary embodiment of the present specification, R2 is methyl.

In the exemplary embodiment of the present specification, Rx and Rz are the same as or different from each other, and are each independently an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, Rx and Rz are the same as or different from each other, and are each independently an alkyl group having 1 to 8 carbon atoms.

In the exemplary embodiment of the present specification, Rx and Rz are the same as or different from each other, and are each independently an alkyl group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, Rx and Rz are the same as or different from each other, and each independently methyl; Isopropyl; Or 1-ethylpropyl.

In an exemplary embodiment of the present specification. Ry is hydrogen.

In the exemplary embodiment of the present specification, n1 is 1.

In the exemplary embodiment of the present specification, n2 is 1.

In the exemplary embodiment of the present specification, the sum of n1 and n2 is 1.

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

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

The definitions of L1, L2, Y1, Y2, R1, R2, Rx, Ry, Rx, a and b are the same as those defined in Formula 1.

In an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 2-1 to 2-6.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

In Formulas 2-1 to 2-6,

The definitions of L1, Y1, R1, R2, Rx, Ry, Rz and b are the same as those defined in Formula 1,

a is an integer of 0 to 5, and when a is 2 or more, R1s are the same as or different from each other.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 2-1 and 2-3 to 2-6 below.

In an exemplary embodiment of the present specification, Formula 1 is represented by any one of Formulas 2-7 to 2-10 below.

[Formula 2-7]

[Formula 2-8]

[Formula 2-9]

[Chemical Formula 2-10]

In Formula 2-7 to Formula 2-10,

The definitions of L2, Y2, R1, R2, Rx, Ry, Rz, a and b are the same as those defined in Formula 1.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 3.

[Formula 3]

In Chemical Formula 3,

The definitions of L2, Y2, R1, R2, Rx, Ry, Rz and a are the same as those defined in Formula 1,

b is an integer of 0 to 3, and when b is 2 or more, R2 is the same as or different from each other,

m1 and m2 are each an integer of 1 to 10.

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

In the exemplary embodiment of the present specification, m2 is 1.

In the exemplary embodiment of the present specification, when n1 is 1 and n2 is 0, (1) Y1 is a heterocyclic ketone group; Carbocyclic ketone group; Monocyclic or polycyclic aryl groups; Monocyclic or polycyclic aliphatic heterocyclic group; Or a monocyclic or polycyclic aromatic heterocyclic group, or (2) Formula 1 is represented by the following Formula 5.

[Formula 5]

In Formula 5,

Y1 is a cycloalkyl group; Or a monocyclic or polycyclic aliphatic hydrocarbon ring group,

e1 is an integer from 0 to 5, and when e1 is 2 or more, R1 is the same as or different from each other,

e2 is an integer of 0 to 2, and when e2 is 2, R2 is the same as or different from each other,

G1 and G2 are the same as or different from each other, and each independently an alkyl group,

The definitions of L1, R1, R2, Rx, Ry, and Rz are as defined in Formula 1.

In the exemplary embodiment of the present specification, when n1 is 1 and n2 is 0, (1) Y1 is a heterocyclic ketone group; Carbocyclic ketone group; Monocyclic or polycyclic aryl groups; Or a monocyclic or polycyclic aromatic heterocyclic group, or (2) Formula 1 is represented by the following Formula 6.

[Formula 6]

In Formula 6,

Y1 is a cycloalkyl group; Monocyclic or polycyclic aliphatic hydrocarbon ring groups; Or a monocyclic or polycyclic aliphatic heterocyclic group,

c1 is an integer from 0 to 5, and when c1 is 2 or more, R1 is the same as or different from each other,

c2 is an integer of 0 to 2, and when c2 is 2, R2 is the same as or different from each other,

G1 and G2 are the same as or different from each other, and each independently an alkyl group,

The definitions of L1, R1, R2, Rx, Ry, and Rz are as defined in Formula 1.

In the exemplary embodiment of the present specification, when n1 is 1 or more, Y1 is a heterocyclic ketone group; Carbocyclic ketone group; Monocyclic or polycyclic aryl groups; Monocyclic or polycyclic aliphatic heterocyclic group; Or a monocyclic or polycyclic aromatic heterocyclic group.

In the exemplary embodiment of the present specification, when n1 is 1 or more, Y1 is a heterocyclic ketone group; Carbocyclic ketone group; Monocyclic or polycyclic aryl groups; Or a monocyclic or polycyclic aromatic heterocyclic group.

In the exemplary embodiment of the present specification, when n1 is 1 and n2 is 0, Formula 1 is represented by the following Formula 7.

[Formula 7]

In Formula 7,

d1 is an integer of 0 to 5, and when d1 is 2 or more, R1 is the same as or different from each other,

d2 is an integer of 0 to 2, and when d2 is 2, R2 is the same as or different from each other,

G3 and G4 are the same as or different from each other, and each independently an alkyl group,

The definitions of L1, Y1, R1, R2, Rx, Ry, and Rz are as defined in Formula 1.

In the exemplary embodiment of the present specification, when n1 is 1 and n2 is 0, Chemical Formula 1 is represented by Chemical Formula 7, and in Chemical Formula 7, Y1 is a heterocyclic ketone group; Carbocyclic ketone group; Monocyclic or polycyclic aryl groups; Monocyclic or polycyclic aliphatic heterocyclic group; Or a monocyclic or polycyclic aromatic heterocyclic group.

In the exemplary embodiment of the present specification, when n1 is 1 and n2 is 0, Chemical Formula 1 is represented by Chemical Formula 7, and in Chemical Formula 7, Y1 is a heterocyclic ketone group; Carbocyclic ketone group; Monocyclic or polycyclic aryl groups; Or a monocyclic or polycyclic aromatic heterocyclic group.

In the exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently deuterium; Or an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently deuterium; Or an alkyl group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently deuterium; Or it is a C1-C3 alkyl group.

In the exemplary embodiment of the present specification, G1 and G2 are each methyl.

In the exemplary embodiment of the present specification, G3 and G4 are the same as or different from each other, and each independently deuterium; Or an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, G3 and G4 are the same as or different from each other, and each independently deuterium; Or an alkyl group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, G3 and G4 are the same as or different from each other, and each independently deuterium; Or it is a C1-C3 alkyl group.

In the exemplary embodiment of the present specification, G3 and G4 are each methyl.

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

In the exemplary embodiment of the present specification, the compound represented by Formula 1 may be prepared according to the method of Formula 1 below.

[General Formula 1]

In General Formula 1, the definitions of L1, L2, Y1, Y2, R1, R2, Rx, Ry, Rz, a, b, n1 and n2 are the same as those defined in Formula 1.

Formula 1 is an example of a method of forming a compound represented by Formula 1, and the method for synthesizing the compound represented by Formula 1 is not limited to Formula 1, and some synthesis steps are known in the art. It can be done by way.

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

An exemplary embodiment of the present specification is an organic light emitting device including a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the compound represented by Formula 1 is It provides an organic light-emitting device that is included in one or more of the one or more organic material layers.

The organic light emitting device of the present specification may include a single layer or a multilayer organic material layer between the first electrode and the second electrode. For example, the organic material layer included in the organic light emitting device of the present invention includes a hole injection layer, a hole transport layer, a layer for simultaneously transporting and injecting holes, a hole controlling layer, a light emitting layer, an electron controlling layer, an electron transport layer, an electron injection layer, and an electron transport layer. It may be one or more of the layers simultaneously injected.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is included in at least one layer of the at least one emission layer.

In the exemplary embodiment of the present specification, the emission layer including the compound represented by Formula 1 is a red emission layer.

In the exemplary embodiment of the present specification, when one or more emission layers are included in the organic light emitting device, each emission layer may exhibit a different color.

In the exemplary embodiment of the present specification, the organic light-emitting device including the compound represented by Formula 1 is a red organic light-emitting device.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is included in an amount of 1 part by weight or more and 10 parts by weight or less based on 100 parts by weight of the total light emitting layer including the compound.

In the exemplary embodiment of the present specification, the emission layer including the compound represented by Chemical Formula 1 further includes a host material.

In the exemplary embodiment of the present specification, the host material included in the light emitting layer including the compound represented by Formula 1 is a carbazole derivative compound or an aromatic polycyclic compound containing N.

In the exemplary embodiment of the present specification, the emission layer including the compound represented by Formula 1 further includes a host compound represented by the following Formula H.

[Formula H]

In the formula H,

G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Alkyl group; Cycloalkyl group; Silyl group; Aryl group; Or a heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,

G3 and G4 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; Or a heterocyclic group unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group,

b1 is an integer from 0 to 7, and when b1 is 2 or more, a plurality of G1s are the same or different from each other,

b2 is an integer of 0 to 7, and when b2 is 2 or more, a plurality of G2s are the same or different from each other.

In the exemplary embodiment of the present specification, G1 is combined with an adjacent group to form a benzene ring.

In the exemplary embodiment of the present specification, G4 is a heterocyclic group that is unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group and includes N.

In the exemplary embodiment of the present specification, G4 is a heterocyclic group which is unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group, and includes a 6-membered ring including N.

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

[Formula H-1]

In the formula H-1,

The definitions of G1 to G4 and b2 are the same as those defined in Formula H,

b3 is an integer of 0 to 9, and when b3 is 2 or more, a plurality of G1s are the same or different.

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

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is included in at least one of a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes, and a hole control layer.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is included in at least one of an electron injection layer, an electron transport layer, a layer that simultaneously injects and transports electrons, and an electron control layer.

In the exemplary embodiment of the present specification, 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.

In the exemplary embodiment of the present specification, the organic light emitting device may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

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

The organic light emitting device according to an exemplary embodiment of the present invention may include a substrate 1, an anode 2, an organic material layer 3, and a cathode 4, as shown in FIG. 1. In an exemplary embodiment, the compound represented by Formula 1 is included in the organic material layer (3).

The organic light emitting device according to an exemplary embodiment of the present invention includes a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6, and a second hole transport layer 7, as shown in FIG. 2. ), a light emitting layer 8, an electron transport layer 9, an electron injection layer 10, and a cathode 4. In an exemplary embodiment, the compound represented by Formula 1 is included in the light-emitting layer 8.

3 is a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, a light emitting layer 8, an electron injection and transport layer 11 and a cathode. An example of the organic light-emitting device made of (4) is shown. In an exemplary embodiment, the compound represented by Formula 1 is included in the light-emitting layer 8.

However, the structure of the organic light-emitting device according to the exemplary embodiment of the present specification is not limited to FIGS. 1 to 3 and may be any one of the following structures.

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

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

(3) Anode/Hole Transport Layer/Light-Emitting Layer/Electron Transport Layer/Anode

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

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

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

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

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

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

(10) Anode/Hole injection layer/Hole transport layer/Hole control layer/Light emitting layer/Electron transport layer/Electron injection layer/Anode

(11) Anode/Hole Transport Layer/Light-Emitting Layer/Electron Control Layer/Electron Transport Layer/Anode

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

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

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

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

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

In addition, the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution 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 (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

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.

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

The hole injection 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 prevents the movement 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 the emission 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, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion.

The hole control layer is a layer that prevents the flow of electrons into the light emitting layer to the anode and controls the flow of holes flowing into the light emitting layer to control the performance of the entire device. The hole control material is preferably a compound having the ability to prevent the inflow of electrons from the light-emitting layer to the anode and to control the flow of holes injected into the light-emitting layer or the light-emitting material. In an exemplary embodiment, an arylamine-based organic material may be used as the hole control layer, but is not limited thereto.

The light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding 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 include a host material and a dopant material.

The host material may be a condensed aromatic ring derivative or a heterocyclic-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 dibenzofuran derivatives, ladder furan compounds, And pyrimidine derivatives, but are not limited thereto.

Examples of the dopant material for the light emitting layer include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. 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.

The electron control layer is a layer that blocks the inflow 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 electron controlling material is preferably a compound having the ability to prevent the inflow of holes from the light emitting layer to the cathode and to control electrons injected into the light emitting layer or the light emitting material. As the electron controlling material, a suitable material may be used according to the configuration of the organic material layer used in the device. The electron control 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 is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons well from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Examples of the electron transport material include Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired negative electrode material as used according to the prior art. In one embodiment, the negative electrode material is a material having a low work function; And an aluminum layer or a silver layer. Examples of the material having the low work function include cesium, barium, calcium, ytterbium, and samarium, and an aluminum layer or a silver layer may be formed on the layer after forming a layer with the material.

The electron injection layer is a layer for injecting electrons received from an electrode into the light emitting layer. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and transfer of excitons generated in the light emitting layer to the hole injection layer or the hole injection material In addition, it is preferable to use a compound having excellent thin film forming ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, benzimidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. Derivatives thereof, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

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

Hereinafter, for a detailed understanding of the present invention, a method of manufacturing the compound of the present invention and an organic light-emitting device including the same will be described.

Preparation Example 1: Synthesis of Compound 1

(1) Synthesis of Intermediate 2-A

Compound 1-A (18.9g, 60mmol), IrCl ₃ (6.847g, 22.95mmol), 2-ethoxyethanol 225ml and DI-Water 75ml were added to a round bottom flask under nitrogen and refluxed for a day. After the reaction was completed, the temperature was lowered, filtered under reduced pressure, and washed with methanol to prepare compound 2-A. (9.8g, yield 49%)

(2) Synthesis of compound 1

Compound 2-A (9g, 5.25mmol), potassium carbonate (7.26g, 52.53mmol), and pentane-2,4-dione (5.26) in a round bottom flask under nitrogen g, 52.53mmol) and 300ml of 2-ethoxyethanol were added and stirred at room temperature for 48 hours. The resulting precipitate was filtered under reduced pressure and washed with methanol. Compound 1 was prepared by separation through column chromatography. (4g, yield 41%, MS:[M+H] ⁺ =921)

Preparation Example 2: Synthesis of Compound 2

(1) Synthesis of Intermediate 2-B

Compound 1-B (18.9g, 60mmol), IrCl ₃ (6.847g, 22.95mmol), 2-ethoxyethanol 225ml and DI-Water 75ml were added to a round bottom flask under nitrogen and refluxed for a day. After the reaction was completed, the temperature was lowered, filtered under reduced pressure, and washed with methanol to prepare compound 2-B. (9.1 g, yield 46%)

(2) Synthesis of compound 2

Compound 2-B (9 g, 5.25 mmol), potassium carbonate (7.26 g, 52.53 mmol), and pentane-2,4-dione (5.26) in a round bottom flask under nitrogen. g, 52.53mmol) and 300ml of 2-ethoxyethanol were added and stirred at room temperature for 48 hours. The resulting precipitate was filtered under reduced pressure and washed with methanol. Separated through column chromatography to prepare compound 2. (3.8g, yield 39%, MS:[M+H] ⁺ =921)

Preparation Example 3: Synthesis of Compound 3

(1) Synthesis of Intermediate 2-C

Compound 1-C (18.9g, 60mmol), IrCl ₃ (6.847g, 22.95mmol), 2-ethoxyethanol 225ml and DI-Water 75ml were added to a round bottom flask under nitrogen and refluxed for a day. After the reaction was completed, the temperature was lowered, filtered under reduced pressure, and washed with methanol to prepare compound 2-C. (9.4g, yield 47%)

(2) Synthesis of compound 3

Compound 2-C (9g, 5.25mmol), potassium carbonate (7.26g, 52.53mmol), pentane-2,4-dione (5.26) in a round bottom flask under nitrogen g, 52.53mmol) and 300ml of 2-ethoxyethanol were added and stirred at room temperature for 48 hours. The resulting precipitate was filtered under reduced pressure and washed with methanol. Separated through column chromatography to prepare compound 3. (4.1g, yield 42%, MS:[M+H] ⁺ =921)

Preparation Example 4: Synthesis of Compound 4

(1) Synthesis of Intermediate 2-D

Compound 1-D (20.65g, 60mmol), IrCl ₃ (6.847g, 22.95mmol), 2-ethoxyethanol 225ml and DI-Water 75ml were added to a round bottom flask under nitrogen and refluxed for a day. After completion of the reaction, the temperature was lowered, filtered under reduced pressure, and washed with methanol to prepare compound 2-D. (8.7g, yield 41%)

(2) Synthesis of compound 4

Compound 2-D (8g, 4.37mmol), potassium carbonate (6.045g, 43.74mmol), pentane-2,4-dione (4.38) in a round bottom flask under nitrogen g, 43.74mmol), and 300ml of 2-ethoxyethanol were added and stirred at room temperature for 48 hours. The resulting precipitate was filtered under reduced pressure and washed with methanol. Separated through column chromatography to prepare compound 4. (3.7 g, yield 43%, MS: [M+H] ⁺ =979)

Preparation Example 5: Synthesis of Compound 5

(1) Synthesis of Intermediate 2-E

Compound 1-E (20.65g, 60mmol), IrCl ₃ (6.847g, 22.95mmol), 2-ethoxyethanol 225ml and DI-Water 75ml were added to a round bottom flask under nitrogen and refluxed for one day. After the reaction was completed, the temperature was lowered, filtered under reduced pressure, and washed with methanol to prepare compound 2-E. (9g, 43% yield)

(2) Synthesis of compound 5

Compound 2-E (9g, 4.92mmol), potassium carbonate (6.8g, 49.21mmol), and pentane-2,4-dione (4.93) in a round bottom flask under nitrogen. g, 49.21 mmol) and 300 ml of 2-ethoxyethanol were added and stirred at room temperature for 48 hours. The resulting precipitate was filtered under reduced pressure and washed with methanol. Separated through column chromatography to prepare compound 5. (4.1g, yield 43%, MS:[M+H] ⁺ =979)

Preparation Example 6: Synthesis of Compound 6

(1) Synthesis of Intermediate 2-F

Compound 1-F (20g, 58mmol), IrCl ₃ (6.847g, 22.95mmol), 2-ethoxyethanol 225ml and DI-Water 75ml were added to a round bottom flask under nitrogen and refluxed for a day. After the reaction was completed, the temperature was lowered, filtered under reduced pressure, and washed with methanol to prepare compound 2-F. (8.2 g, yield 39%)

(2) Synthesis of compound 6

Compound 2-F (8 g, 4.4 mmol), calcium carbonate (6.07 g, 43.93 mmol), and pentane-2,4-dione (4.4) in a round bottom flask under nitrogen. g, 43.93mmol) and 300ml of 2-ethoxyethanol were added and stirred at room temperature for 48 hours. The resulting precipitate was filtered under reduced pressure and washed with methanol. Separated through column chromatography to prepare compound 6. (3.4g, yield 39%, MS:[M+H] ⁺ =975)

Preparation Example 7: Synthesis of Compound 7

(1) Synthesis of Intermediate 2-G

Compound 1-G (20g, 69mmol), IrCl- ₃ (6.847g, 22.95mmol), 2-ethoxyethanol 225ml, and DI-Water 75ml were added to a round bottom flask under nitrogen and refluxed for a day. After the reaction was completed, the temperature was lowered, filtered under reduced pressure, and washed with methanol to prepare compound 2-G. (5.4 g, yield 46%)

(2) Synthesis of compound 7

Compound 2-G (5g, 4.86mmol), potassium carbonate (6.72g, 48.63mmol), and pentane-2,4-dione (4.86mmol) in a round bottom flask under nitrogen g, 48.63mmol), and 300ml of 2-ethoxyethanol were added and stirred at room temperature for 48 hours. The resulting precipitate was filtered under reduced pressure and washed with methanol. Separated through column chromatography to prepare compound 7. (3.2g, yield 38%, MS:[M+H] ⁺ =865)

Preparation Example 8: Synthesis of Compound 8

(1) Synthesis of Intermediate 2-H

Compound 1-H (20g, 63.2mmol), IrCl ₃ (6.847g, 22.95mmol), 2-ethoxyethanol 225ml and DI-Water 75ml were added to a round bottom flask under nitrogen and refluxed for a day. After the reaction was completed, the temperature was lowered, filtered under reduced pressure, and washed with methanol to prepare compound 2-H. (8.1 g, yield 41%)

(2) Synthesis of compound 8

Compound 2-H (8g, 4.71mmol), potassium carbonate (4.03g, 29.12mmol), pentane-2,4-dione (2.92) in a round bottom flask under nitrogen g, 29.12mmol), and 300ml of 2-ethoxyethanol were added and stirred at room temperature for 48 hours. The resulting precipitate was filtered under reduced pressure and washed with methanol. Compound 8 was prepared by separation through column chromatography. (1.9g, yield 35%, MS:[M+H] ⁺ =923)

Preparation Example 9: Synthesis of Compound 9

Compound 9 was synthesized in the same manner as in Preparation Example 1, except that 2,6-dimethylheptane-3,5-dione was used instead of acetylacetone. (MS:[M+H] ⁺ =977)

Preparation Example 10: Synthesis of Compound 10

Compound 10 was synthesized by the same method except that 2,6-dimethylheptane-3,5-dione was used instead of acetylacetone in Preparation Example 2. (MS:[M+H] ⁺ =977)

Preparation Example 11: Synthesis of Compound 11

Compound 11 was synthesized in the same manner as in Preparation Example 3, except that 2,6-dimethylheptane-3,5-dione was used instead of acetylacetone. (MS:[M+H] ⁺ =977)

Preparation Example 12: Synthesis of Compound 12

Compound 12 was synthesized in the same manner as in Preparation Example 4 except that 2,6-dimethylheptane-3,5-dione was used instead of acetylacetone. (MS:[M+H] ⁺ =1035)

Preparation Example 13: Synthesis of Compound 13

Compound 13 was synthesized in the same manner as in Preparation Example 5, except that 2,6-dimethylheptane-3,5-dione was used instead of acetylacetone. (MS:[M+H] ⁺ =1035)

Preparation Example 14: Synthesis of Compound 14

Compound 14 was synthesized in the same manner as in Preparation Example 6 except for using 2,6-dimethylheptane-3,5-dione instead of acetylacetone. (MS:[M+H] ⁺ =1031)

Preparation Example 15: Synthesis of Compound 15

Compound 15 was synthesized in the same manner as in Preparation Example 7, except that 2,6-dimethylheptane-3,5-dione was used instead of acetylacetone. (MS:[M+H] ⁺ =921)

Preparation Example 16: Synthesis of Compound 16

Compound 16 was synthesized in the same manner as in Preparation Example 8 except that 2,6-dimethylheptane-3,5-dione was used instead of acetylacetone. (MS:[M+H] ⁺ =979)

Preparation Example 17: Synthesis of Compound 17

Compound 17 was synthesized in the same manner as in Preparation Example 1 except that 3,7-diethylnonane-4,6-dione was used instead of acetylacetone. (MS :[M+H] ⁺ =1033)

Preparation Example 18: Synthesis of Compound 18

Compound 18 was synthesized in the same manner as in Preparation Example 2, except that 3,7-diethylnonane-4,6-dione was used instead of acetylacetone. (MS:[M+H] ⁺ =1033)

Preparation Example 19: Synthesis of Compound 19

Compound 19 was synthesized in the same manner as in Preparation Example 3, except that 3,7-diethylnonane-4,6-dione was used instead of acetylacetone. (MS:[M+H] ⁺ =1033)

Preparation Example 20: Synthesis of Compound 20

Compound 20 was synthesized in the same manner as in Preparation Example 4, except that 3,7-diethylnonane-4,6-dione was used instead of acetylacetone. (MS:[M+H] ⁺ =1091)

Preparation Example 21: Synthesis of Compound 21

Compound 21 was synthesized in the same manner as in Preparation Example 5, except that 3,7-diethylnonane-4,6-dione was used instead of acetylacetone. (MS:[M+H] ⁺ =1091)

Preparation 22: Synthesis of Compound 22

Compound 22 was synthesized in the same manner as in Preparation Example 6, except that 3,7-diethylnonane-4,6-dione was used instead of acetylacetone. (MS:[M+H] ⁺ =1087)

Preparation 23: Synthesis of Compound 23

Compound 23 was synthesized in the same manner as in Preparation Example 7, except that 3,7-diethylnonane-4,6-dione was used instead of acetylacetone. (MS:[M+H] ⁺ =977)

Preparation Example 24: Synthesis of Compound 24

Compound 24 was synthesized in the same manner as in Preparation Example 8, except that 3,7-diethylnonane-4,6-dione was used instead of acetylacetone. (MS:[M+H] ⁺ =1035)

Preparation Example 25: Synthesis of Compound 25

(1) Synthesis of Intermediate 2-I

Compound 1-I (18.5g, 63.9mmol), IrCl ₃ (6.847g, 22.95mmol), 2-ethoxyethanol 225ml and DI-Water 75ml were added to a round bottom flask under nitrogen and refluxed for a day. . After the reaction was completed, the temperature was lowered, filtered under reduced pressure, and washed with methanol to prepare compound 2-I. (7.9g, yield 42.7%)

(2) Synthesis of compound 25

In a round bottom flask under nitrogen, compound 2-I (7 g, 4.35 mmol), calcium carbonate (6.01 g, 43.5 mmol), and pentane-2,4-dione (4.56) g, 43.51mmol) and 300ml of 2-ethoxyethanol were added and stirred at room temperature for 48 hours. The resulting precipitate was filtered under reduced pressure and washed with methanol. Separated through column chromatography to prepare compound 25. (3g, yield 39.7%, MS:[M+H] ⁺ =869)

Preparation 26: Synthesis of Compound 26

(1) Synthesis of Intermediate 2-J

Compound 1-J (20.3g, 63.9mmol), IrCl ₃ (6.847g, 22.95mmol), 2-ethoxyethanol 225ml and DI-Water 75ml were added to a round bottom flask under nitrogen and refluxed for a day. . After the reaction was completed, the temperature was lowered, filtered under reduced pressure, and washed with methanol to prepare compound 2-J. (13.2g, yield 48%)

(2) Synthesis of compound 26

Compound 2-J (7.48g, 4.35mmol), potassium carbonate (6.01g, 43.5mmol), pentane-2,4-dione (Pentane-2,4-dione) ( 4.56g, 43.51mmol) and 2-ethoxyethanol (300ml) were added and stirred at room temperature for 48 hours. The resulting precipitate was filtered under reduced pressure and washed with methanol. Compound 26 was prepared by separating through column chromatography. (1.4g, yield 35.4%, MS:[M+H] ⁺ =924)

Example 1

Fischer Co.'s product was used, and distilled water was Millipore Co. Distilled water filtered secondarily with the product's filter was used. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying. On the prepared ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT-CN) was thermally vacuum deposited to a thickness of 50Å to form a hole injection layer. The following HT1 compound for transporting holes was vacuum-deposited thereon, followed by depositing the following HT2 compound to form first (700Å) and second hole transport layers (200Å). Next, the following H1 compound and Compound 1 were vacuum-deposited so that 3 parts by weight of Compound 1 based on 100 parts by weight of the total weight of the following H1 compound and Compound 1 were deposited on the second hole transport layer to form a light emitting layer (300Å). Then, the following E0 compound was sequentially thermally vacuum deposited (300Å) as an electron injection and transport layer. Lithium fluoride (LiF) having a thickness of 12 Å and aluminum having a thickness of 2,000 Å were sequentially deposited on the electron transport layer to form a cathode, and then an organic light emitting device was manufactured. In the above process, the deposition rate of organic material was maintained at 1 Å/sec, the deposition rate of LiF was 0.2 Å/sec, and the deposition rate of aluminum was maintained at 3 Å/sec to 7 Å/sec.

Examples 2 to 10

The organic light emitting devices of Examples 2 to 10 were manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of Compound 1 as the phosphorescent dopant when forming the emission layer.

Comparative Examples 1 to 7

Organic light-emitting devices of Comparative Examples 1 to 7 were manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of Compound 1 as a phosphorescent dopant when forming the light emitting layer.

Table 1 shows the results of the organic light emitting diodes manufactured according to Examples 1 to 10 and Comparative Examples 1 to 7. Voltage, efficiency, and emission color are data at 5000nit luminance. The lifetime is the time when the initial photocurrent value is 100% and the photocurrent value is 98%.

Dopant
matter Driving voltage (V) Efficiency (cd/A) life span
(T98, h,) Example 1 One 4.6 30.2 52 Example 2 5 4.5 30.4 56 Example 3 7 4.7 31.8 50 Example 4 10 4.5 30.0 58 Example 5 12 4.6 29.5 50 Example 6 16 4.7 31.24 48 Example 7 19 4.6 31.3 52 Example 8 22 4.5 30.8 49 Example 9 25 4.6 29.5 56 Example 10 26 4.6 33.8 56 Comparative Example 1 E1 4.6 25.1 35 Comparative Example 2 E2 4.7 25.1 32 Comparative Example 3 E3 4.8 25.4 40 Comparative Example 4 E4 4.6 24.8 37 Comparative Example 5 E5 4.5 25.3 34 Comparative Example 6 E6 4.6 26.8 42 Comparative Example 7 E7 4.6 24.5 35

As can be seen from Table 1, when the compound of the present invention was used as a phosphorescent dopant material, it was confirmed that the compound of the present invention exhibited excellent properties in terms of life as compared to Comparative Examples using compounds E1 to E7. Through this, it was confirmed that the type of substituent affects the efficiency and life. In particular, it is judged that better performance was achieved through the control of π-π bonding between compounds.

1: substrate
2: anode
3: organic material layer
4: cathode
5: hole injection layer
6: first hole transport layer
7: second hole transport layer
8: light emitting layer
9: electron transport layer
10: electron injection layer
11: electron injection and transport layer

Claims (12)

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

In Formula 1,
L1 and L2 are the same as or different from each other, and are each independently a linear or branched chain alkylene group having 1 to 10 carbon atoms,
Y1 and Y2 are the same as or different from each other, and each independently a cycloalkyl group having 3 to 8 carbon atoms; A heterocyclic ketone group having 2 to 12 carbon atoms; Or a monocyclic or polycyclic aliphatic heterocyclic group having 2 to 20 carbon atoms,
R1 and Ry are each hydrogen,
R2 is hydrogen or an alkyl group having 1 to 10 carbon atoms,
Rx and Rz are the same as or different from each other, and are each independently an alkyl group having 1 to 10 carbon atoms,
n1 is 0 or 1,
n2 is 0 or 1,
the sum of n1 and n2 is 1 or more,
a is an integer from 0 to 6,
b is an integer of 0 to 4, and when b is 2 or more, a plurality of R2s are the same or different from each other. The compound of claim 1, wherein Formula 1 is represented by any one of the following Formulas 2-1 to 2-6:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

In Formulas 2-1 to 2-6,
The definitions of L1, Y1, R1, R2, Rx, Ry, Rz and b are the same as those defined in Formula 1,
a is an integer from 0 to 5. The compound of claim 1, wherein Formula 1 is represented by any one of the following Formulas 2-7 to 2-10:
[Formula 2-7]

[Formula 2-8]

[Formula 2-9]

[Chemical Formula 2-10]

In Formula 2-7 to Formula 2-10,
The definitions of L2, Y2, R1, R2, Rx, Ry, Rz and a are the same as those defined in Formula 1,
b is an integer of 0 to 3, and when b is 2 or more, R2 is the same as or different from each other. The compound of claim 1, wherein Formula 1 is represented by the following Formula 3:
[Formula 3]

In Chemical Formula 3,
The definitions of Y1, Y2, R1, R2, Rx, Ry, Rz, a, b, n1 and n2 are the same as defined in Formula 1,
m1 and m2 are each independently an integer of 1 to 10. The compound of claim 1, wherein L1 and L2 are each methylene. delete The compound of claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:

. An organic light-emitting device comprising a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the compound according to any one of claims 1 to 5 is 1 An organic light-emitting device that is included in one or more of the organic material layers of the layer or more. The organic light-emitting device of claim 8, wherein the organic material layer includes one or more emission layers, and the compound represented by Formula 1 is included in one or more layers of the one or more emission layers. The organic light-emitting device of claim 9, wherein the light-emitting layer including the compound represented by Formula 1 is a red light-emitting layer. The method according to claim 8, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes, and a hole control layer, and the compound represented by Formula 1 is the hole injection layer and the hole transport layer. An organic light-emitting device that is included in at least one of a layer for simultaneously injecting and transporting holes and a hole controlling layer. The method of claim 8, wherein the organic material layer includes at least one of an electron injection layer, an electron transport layer, a layer for simultaneously injecting and transporting electrons, and an electron controlling layer, and the compound represented by Formula 1 is the electron injection layer and the electron transport layer. , An organic light-emitting device that is included in at least one of a layer and an electron control layer for simultaneously injecting and transporting electrons.

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