KR102201559B1 - 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

A compound and an organic light-emitting device containing the same TECHNICAL FIELD

The present invention 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. 10-2018-0062377 filed with the Korean Intellectual Property Office on May 31, 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. 10-2008-0096733

An object of the present specification is to provide an organic light-emitting device having a low driving voltage, high luminous efficiency, or good lifetime characteristics by including the compound represented by Formula 1.

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

[Formula 1]

In Formula 1,

X is O, S or Se,

L1 and L2 are the same as or different from each other, and each independently an arylene group,

Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group,

m1 and m2 are each independently 0 or 1, and the sum of m1 and m2 is 1,

n1 is an integer of 0 to 4, and when n1 is 2 or more, L1 is the same as or different from each other,

n2 is an integer of 0 to 4, and when n2 is 2 or more, L2 is the same as 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 one or more organic material layers provided between the first electrode and the second electrode, wherein the organic material layer is represented by Formula 1 above. It provides an organic light-emitting device comprising the compound to be displayed.

The compounds described herein can be used as a material for an organic material layer of an organic light-emitting device. In one embodiment, the compound described in the present specification may be used as a material of any one of hole injection, hole transport, hole control, light emission, electron control, electron transport, and electron injection material, particularly a light emitting material.

In an exemplary embodiment, the organic light-emitting device including the compound represented by Formula 1 improves efficiency, lowers driving voltage, or improves lifespan characteristics.

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 hole transport layer 6, a hole control layer 7, a light emitting layer 8, an electron transport layer 9, and an electron injection layer 10. And an example of an organic light-emitting device including the cathode 4 is shown.
3 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 7, a light emitting layer 8, an electron control layer 11, an electron injection and transport layer ( 12) and a cathode 4 are shown.
4 shows a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6a, a second hole transport layer 6b, a light emitting layer 8, an electron control layer 11, and electron injection. And an example of an organic light-emitting device including the transport layer 12 and the cathode 4 is shown.

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.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 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, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, Cyclopentylmethyl, cycloheptylmethyl, octyl, 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, and the like, but are not limited thereto.

In the present specification, an aryl group means wholly or partially unsaturated substituted or unsubstituted monocyclic or polycyclic. Although the number of carbon atoms is not particularly limited, it is preferably 6 to 60 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 40 carbon 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 a phenyl group, a biphenyl group, and a terphenyl group, but are not limited thereto. The polycyclic aryl group is a naphthyl group, anthracenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenalenyl group, pyrenyl group, tetracenyl group, chrysenyl group, pentacenyl group , Fluorenyl group, indenyl group, acenaphthalenyl group, benzofluorenyl group, spirofluorenyl group, 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.

The substituted fluorenyl group may be, for example, any one selected from the following structures, but is not limited thereto.

In the present specification, the heteroaryl group is a cyclic group including at least one of N, O and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the heteroaryl group has 2 to 20 carbon atoms. Examples of the heteroaryl group include a thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, Triazinyl group, triazolyl group, acridinyl group, carbolinyl group, acenaphthoquinoxalinyl group, indenoquinazolinyl group, indenoisoquinolinyl group, indenoquinolinyl group, pyridoindolyl group, pyridazinyl group , Pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyradinyl group, pyrazinopyrazinyl group, isoquinolinyl group, indolyl group, carbazolyl group , Benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, phenanthrolinyl group, isoxazolyl group, thia Diazolyl group, benzothiazolyl group, phenoxazinyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, the arylene group refers to a divalent aryl group, and the description of the aryl group may be applied except that it is divalent.

In the present specification, the heteroarylene group refers to a divalent heteroaryl group, and the description of the heteroaryl group may be applied except that it is divalent.

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

The compound represented by Formula 1 has excellent electron injection ability by including a triazinyl group, and high stability against electrons by including dibenzofuran in which at least one benzene ring is condensed.

In the compound represented by Formula 1, one benzene ring is condensed to a dibenzofuranyl group (the sum of m1 and m2 is 1), thereby forming a dibenzofuranyl group (m1 = 0, m2 = 0) in which the benzene ring is not condensed. Compared to the containing compound, electrons are easily transferred in the compound and the stability to electrons is high.

In the exemplary embodiment of the present specification, X is O.

In the exemplary embodiment of the present specification, X is S.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently an arylene group having 6 to 25 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 an arylene group having 6 to 18 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 an arylene group having 6 to 13 carbon atoms.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each is a phenylene group.

In the exemplary embodiment of the present specification, L1 is an m-phenylene group or a p-phenylene group.

In the exemplary embodiment of the present specification, L2 is a p-phenylene group.

In the exemplary embodiment of the present specification, n1 is 0.

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

In the exemplary embodiment of the present specification, n2 is 0.

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

In the exemplary embodiment of the present specification, when n1 is 1 and n2 is 2, L1 is an m-phenylene group and L2 is a p-phenylene group.

In the exemplary embodiment of the present specification, n1 is 1, n2 is 1, (1) L1 is an m-phenylene group, L2 is a p-phenylene group, or (2) L1 is a direct bond, m-phenyl It is a ene group or a p-phenylene group, and L2 is a direct bond.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 25 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 and Ar2 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, Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 13 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 is a phenyl group.

In the exemplary embodiment of the present specification, Ar2 is a phenyl group.

In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 2.

[Formula 2]

In Formula 2,

The definitions of X, L1, L2, Ar1, Ar2, n1, and n2 are as defined in Chemical 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 X, L1, L2, Ar1, Ar2, n1, and n2 are as defined in Chemical Formula 1.

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

[Formula 2-A]

[Formula 2-B]

[Formula 2-C]

In Formula 2-A to Formula 2-C,

The definitions of X, L1, L2, Ar1, Ar2, n1, and n2 are as defined in Chemical Formula 1.

In the exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 3-A to 3-C.

[Formula 3-A]

[Formula 3-B]

[Chemical Formula 3-C]

In Formula 3-A to Formula 3-C,

The definitions of X, L1, L2, Ar1, Ar2, n1, and n2 are as defined in Chemical Formula 1.

In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 4.

[Formula 4]

In Formula 4,

The definitions of X, L2, Ar1, Ar2, m1, m2, n1 and n2 are as defined in Formula 1.

In an exemplary embodiment of the present specification, Chemical Formula 4 is represented by the following Chemical Formula 4-1 or Chemical Formula 4-2.

[Formula 4-1]

[Formula 4-2]

In Formula 4-1 and Formula 4-2,

The definitions of X, L2, Ar1, Ar2, m1, m2, n1 and n2 are as defined in Chemical Formula 4.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 5.

[Formula 5]

In Formula 5,

The definitions of X, L1, Ar1, Ar2, m1, m2, n1, and n2 are as defined in Chemical Formula 1.

In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 6.

[Formula 6]

In Formula 6,

The definitions of X, L1, L2, Ar1, Ar2, m1, m2, n1, and n2 are as defined in Formula 1.

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

The compound represented by Formula 1 according to the present specification may be prepared as shown in the following General Formula 1.

[General Formula 1]

In General Formula 1, the definitions of X, L1, L2, Ar1, Ar2, n1, n2, m1, and m2 are the same as those defined in Formula 1.

In an exemplary embodiment, the compound represented by Formula 1 is: a) Intermediate 1 is synthesized with dibenzofuran or dibenzothiophene having two halogen groups through a Suzuki reaction, and b) halogen remaining after the reaction After substituting a group with borate, it can be synthesized through Suzuki reaction.

However, the general formula 1 is an example of a method of forming the compound represented by the formula 1, the synthesis method of formula 1 is not limited to the general formula 1, it may be by a method known in the art. .

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 organic material layer is represented by the aforementioned Formula 1 It provides an organic light emitting device containing the compound.

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 invention is an organic material layer, which is a hole injection layer, a hole transport layer, a layer that simultaneously injects and transports holes, a hole control layer, a light-emitting layer, an electron control layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer It may include a layer and the like.

In one embodiment of the present specification, that the organic material layer includes the compound represented by Formula 1 means that when the organic light emitting device includes one or more organic material layers, the compound represented by Formula 1 is one of the one or more organic material layers. It means that it can be included in more than one layer. In this case, the compounds represented by Formula 1 included in two or more organic material layers may be the same or different from each other.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is included in any one organic material layer among one or more organic material layers.

In the exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, a layer for simultaneously injecting and transporting electrons or an electron controlling layer, and simultaneously performing the electron injection layer, the electron transport layer, and electron injection and transport. The layer or the electron controlling layer includes the compound represented by Formula 1.

In the 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.

In the exemplary embodiment of the present specification, the organic material layer includes one or two or more emission layers. When the organic material layer includes two or more emission layers, each of the emission layers may have the same or different colors. In an exemplary embodiment, the organic material layer includes two or more emission layers, and the compound represented by Formula 1 is included in any one emission layer.

In one embodiment of the present specification, two or more light emitting layers may be provided vertically or horizontally.

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 as a host.

In the exemplary embodiment of the present specification, the light emitting layer including the compound represented by Formula 1 further includes at least one host material.

In an exemplary embodiment of the present specification, the content of the compound represented by Formula 1 is 20 parts by weight or more and 100 parts by weight or less based on the total 100 parts by weight of the emission layer; Or 50 parts by weight to 100 parts by weight or less.

In the exemplary embodiment of the present specification, when the emission layer further includes at least one host material in addition to the compound represented by Formula 1, the sum of parts by weight of the compound represented by Formula 1 and the at least one host material is the total amount of the emission layer. 50 parts by weight or more and 100 parts by weight or less based on 100 parts by weight, and the total amount of the compound represented by Formula 1 is 20 parts by weight or more and 95 parts by weight or less based on the total 100 parts by weight of the light emitting layer.

In the exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, a layer for simultaneously transporting and injecting holes, or a layer for controlling holes, and performing the hole injection layer, a hole transport layer, and a hole transporting and injection simultaneously. The layer or hole control layer includes the compound represented by Chemical Formula 1.

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes a compound represented by any one of Formulas 11 to 21 below; And a compound represented by Formula 1 above.

[Formula 11]

In Formula 11,

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

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

G1 to G4 are the same as or different from each other, and each independently an aryl group,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Aryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group,

b1 and b2 are each independently 0 or 1, and the sum of b1 and b2 is 1,

a1 is an integer of 0 to 8, and when a1 is 2 or more, a plurality of R1s are the same or different from each other,

a2 is an integer of 0 to 8, and when a2 is 2 or more, a plurality of R2s are the same as or different from each other,

[Formula 12]

In Formula 12,

X2 is O or N,

L11 is a direct bond; Or an arylene group,

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

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

[Formula 13]

In Formula 13,

X3 is O or S,

L12 is a direct bond or an arylene group,

G7 is an aryl group,

G8 is a heteroaryl group containing O, S or N,

[Formula 14]

In Formula 14,

X4 is a direct bond; Or CRcRd,

Rc and Rd are the same as or different from each other, and each independently hydrogen; Alkyl group; Or an aryl group, or spiro bonded to each other to form a hydrocarbon ring,

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,

a9 is an integer from 0 to 7, and when a9 is 2 or more, a plurality of G9s are the same or different from each other,

a10 is an integer from 0 to 8, and when a10 is 2 or more, a plurality of G10s are the same or different from each other,

[Formula 15]

In Formula 15,

L13 is an arylene group unsubstituted or substituted with a heteroaryl group; Or a heteroarylene group,

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

b13 is an integer of 1 to 3, and when b13 is 2 or more, a plurality of L13s are the same or different from each other,

[Formula 16]

In Formula 16,

X5 and X6 are each independently O or S,

Y1 to Y4 are each independently N or CH,

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

b14 is an integer of 0 to 4, and when b14 is 2 or more, a plurality of L14s are the same or different from each other,

[Formula 17]

In Formula 17,

X7 and X8 are each independently O or S,

G13 to G15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an aryl group,

[Formula 18]

In Formula 18,

L15 and L16 are each independently a direct bond; Arylene group; Or a heteroarylene group,

G16 is a carbazolyl group unsubstituted or substituted with an aryl group; Or an aryl group substituted or unsubstituted indolopyridinyl group,

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

b16 is 1 or 2, and when b16 is 2, two -L16-G16s are the same as or different from each other,

[Formula 19]

[Formula 20]

In Formula 20,

L17 is an arylene group,

X9 is S or O,

[Formula 21]

G18-L19-G19

In Formula 21,

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, Ra and Rb are each a phenyl group.

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

In the exemplary embodiment of the present specification, G1 to G4 are the same as or different from each other, and each independently a phenyl group; Or a biphenyl group.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Aryl group having 6 to 18 carbon atoms; Or it is a C2-C24 heteroaryl group.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Biphenyl group; Or a benzo[4,5]-thieno[3,2-d]pyrimidinyl group.

In the exemplary embodiment of the present specification, b1 is 0 and b2 is 1.

In the exemplary embodiment of the present specification, b1 is 1 and b2 is 0.

In the exemplary embodiment of the present specification, a1 is 0 or 1.

In the exemplary embodiment of the present specification, a2 is 0 or 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; Phenylene group; Or a biphenylene group.

In the exemplary embodiment of the present specification, G5 is a C2-C24 heteroaryl group containing 2 or more N and 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 and unsubstituted or substituted with an aryl group having 6 to 12 carbon atoms.

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

In the exemplary embodiment of the present specification, G6 is an aryl group having 6 to 18 carbon atoms or an aryl group having 6 to 18 carbon atoms unsubstituted or substituted with a (aryl having 6 to 18 carbon atoms) silyl 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 or an aryl group having 6 to 12 carbon atoms unsubstituted or substituted with a (aryl having 6 to 12 carbon atoms) silyl group; Or it is a C2-C12 heteroaryl group.

In the exemplary embodiment of the present specification, G6 is a phenyl group substituted with a triphenylsilyl group; Phenyl group; Biphenyl 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, L12 is a direct bond; Phenylene group; Or a biphenylene group.

In the exemplary embodiment of the present specification, G8 is a heteroaryl group having 2 to 16 carbon atoms including O, S or N.

In the exemplary embodiment of the present specification, G8 is a carbazolyl 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; heavy hydrogen; An aryl group having 6 to 12 carbon atoms unsubstituted or substituted with a cyano group; Or it is a C2-C16 heteroaryl group.

In the exemplary embodiment of the present specification, Rc and Rd are the same as or different from each other, and each independently hydrogen; An alkyl group having 1 to 6 carbon atoms; Or an aryl group having 6 to 12 carbon atoms, or spiro bonded to each other to form a hydrocarbon ring having 2 to 16 carbon atoms.

In the exemplary embodiment of the present specification, Rc and Rd are the same as or different from each other, and each independently hydrogen; Methyl group; Or a phenyl group, each is a phenyl group and is spiro bonded to each other to form a fluorene ring.

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

In the exemplary embodiment of the present specification, a9 is 0 or 1.

In the exemplary embodiment of the present specification, a10 is 0 or 1.

In the exemplary embodiment of the present specification, L13 is an arylene group having 6 to 16 carbon atoms unsubstituted or substituted with a heteroaryl group having 2 to 16 carbon atoms; Or a C2-C16 heteroarylene group.

In the exemplary embodiment of the present specification, L13 is an arylene group having 6 to 12 carbon atoms unsubstituted or substituted with a heteroaryl group having 2 to 12 carbon atoms; Or it is a C2-C12 heteroarylene group.

In the exemplary embodiment of the present specification, L13 is a biphenylene group unsubstituted or substituted with a dibenzofuranyl group; Divalent dibenzofuranyl group; Or a divalent pyridinyl 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, G11 and G12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it is a C2-C16 heteroaryl group containing O or S.

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

In the exemplary embodiment of the present specification, L14 is a direct bond; An arylene group having 6 to 16 carbon atoms unsubstituted or substituted with a heteroarylene group having 2 to 16 carbon atoms; Or a C2-C16 heteroarylene 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 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; 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, X7 and X8 are each O.

In the exemplary embodiment of the present specification, X7 and X8 are each S.

In the exemplary embodiment of the present specification, G13 and G14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or 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 each independently hydrogen; heavy hydrogen; Or 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 hydrogen; heavy hydrogen; Phenyl group; 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 and L16 are the same as or different from each other, and each independently a direct bond; Arylene group; Or it is a heteroarylene group containing N.

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

In the exemplary embodiment of the present specification, L16 is a direct bond or a biphenylene group.

In the exemplary embodiment of the present specification, G17 is hydrogen; Aryl group having 6 to 22 carbon atoms; Or a C2 to C16 heteroaryl group unsubstituted or substituted with a C2 to C12 aryl group.

; 또는

이다.In the exemplary embodiment of the present specification, G17 is hydrogen; Carbazolyl group; Dibenzofuranyl group; Triphenylenyl group;

; or

to be.

In the exemplary embodiment of the present specification, X9 is S.

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 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, G18 is an aryl group; Or a heteroaryl group containing O or S.

In the exemplary embodiment of the present specification, G18 is a phenyl group; Biphenyl group; Terphenyl group; Or a triphenylenyl 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, G19 is an aryl group; Or a heteroaryl group containing O or S.

In the exemplary embodiment of the present specification, G19 is a phenyl group; Biphenyl group; Dibenzofuranyl group; Or a dibenzothiophenyl 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, L19 is a direct bond; Phenylene group; Biphenylene group; Or terphenylene group.

In the exemplary embodiment of the present specification, the compound represented by Formula 11 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Formula 12 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Formula 13 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Formula 14 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Formula 15 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Formula 16 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Formula 17 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Formula 18 is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the compound represented by Formula 19 is any one selected from the following compounds.

In an exemplary embodiment of the present specification, the compound represented by Formula 20 is the following compound.

In the exemplary embodiment of the present specification, the compound represented by Formula 21 is any one selected from the following compounds.

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 an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 4.

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 hole transport layer 6, a hole control layer 7, and a light emitting layer, as shown in FIG. (8), the electron transport layer 9, the electron injection layer 10 and may be made of a cathode (4). In an exemplary embodiment, the compound represented by Formula 1 is included in the light-emitting layer 8. In another exemplary embodiment, the compound represented by Formula 1 is included in one or more layers of the hole transport layer 5, the hole transport layer 6, and the hole control layer 7. In another exemplary embodiment, the compound represented by Formula 1 is included in at least one of the electron transport layer 9 and the electron injection layer 10.

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 hole transport layer 6, a hole control layer 7, as shown in FIG. The emission layer 8, the electron control layer 11, the electron injection and transport layer 12, and the cathode 4 may be formed. In an exemplary embodiment, the compound represented by Formula 1 is a hole injection layer 5, a hole transport layer 6, a hole control layer 7, a light-emitting layer 8, an electron control layer 11, or an electron injection and transport layer. Can be included in (12).

The organic light emitting device according to an exemplary embodiment of the present invention is a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6a, and a second hole transport layer, as shown in FIG. 4. 6b), a light emitting layer 8, an electron control layer 11, an electron injection and transport layer 12 and a cathode 4 may be formed. In an exemplary embodiment, the compound represented by Formula 1 is a hole injection layer 5, a first hole transport layer 6a, a second hole transport layer 6b, a light emitting layer 8, an electron control layer 11, or an electron It may be included in the injection and transport layer 12.

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 4 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 multilayered 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 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 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.

In the exemplary embodiment of the present specification, the organic light emitting device includes two or more hole transport layers, and materials of the two or more hole transport layers are the same or different from each other.

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 one embodiment, an arylamine-based organic material may be used for 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. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. 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. The electron transport material is a material capable of receiving electrons from the cathode and transferring them to the light emitting 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 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, the present invention will be described in more detail through examples according to the present invention and comparative examples not according to the present invention, but the scope of the present invention is not limited by the examples presented below.

<Production Example>

The compound represented by Formula 1 1) prepares dibenzofuran or dibenzothiophene substituted with two types of halide, 2) introduces boronic acid into one halide, and 3) the other halide It can be prepared from the process of introducing a'substituent including a triazinyl group' after substitution with borate through borylation. 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-bromo-6-chlorodibenzo[b,d]furan 30g (106.6mmol), naphtho[1,2-b]benzofuran-5-ylboronic acid 107mmol, tetrahydrofuran 200mL and water 100mL Mixed and heated to 60°C. Potassium carbonate (319.8 mmol) and tetrakistriphenylphosphine palladium (1.1 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 40.6 g of compound 1-A. (Yield 91%, MS[M+H] ⁺ = 419)

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

Synthesis of Compound 1-A, except that naphtho[2,1-b]benzofuran-10-ylboronic acid was used instead of naphtho[1,2-b]benzofuran-5-ylboronic acid Compound 1-B 41.5g was obtained by the same method as the method. (Yield 93%, MS[M+H] ⁺ = 419)

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

Synthesis of Compound 1-A, except that naphtho[2,3-b]benzofuran-4-ylboronic acid was used instead of naphtho[1,2-b]benzofuran-5-ylboronic acid Compound 1-C 40.2g was obtained by the same method as the method. (Yield 90%, MS[M+H] ⁺ = 419)

Preparation Example 1-4: Synthesis of Compound 1-D

Except that (3-(naphtho[1,2-b]benzofuran-5-yl)phenyl)boronic acid was used instead of naphtho[1,2-b]benzofuran-5-ylboronic acid. , Compound 1-D 46.4g was obtained by the same method as the synthesis method of compound 1-A. (Yield 88%, MS[M+H] ⁺ = 495)

Preparation Example 1-5: Synthesis of Compound 1-E

Except that (3-(naphtho[2,1-b]benzofuran-10-yl)phenyl)boronic acid was used instead of naphtho[1,2-b]benzofuran-5-ylboronic acid. , Compound 1-E 45.9g was obtained by the same method as the synthesis method of compound 1-A. (Yield 87%, MS[M+H] ⁺ = 495)

Preparation Example 1-6: Synthesis of Compound 1-F

Except that (4-(naphtho[2,3-b]benzofuran-4-yl)phenyl)boronic acid was used instead of naphtho[1,2-b]benzofuran-5-ylboronic acid. , Compound 1-F 46.9g was obtained by the same method as the synthesis method of compound 1-A. (Yield 89%, MS[M+H] ⁺ = 495)

Preparation Example 1-7: Synthesis of Compound 1-G

4-bromo-6-chlorodibenzo[b,d]thiophene 31.7g (106.6mmol), naphtho[1,2-b]benzofuran-5-ylboronic acid 107mmol, tetrahydrofuran 200mL and water 100 mL were mixed and heated to 60°C. Potassium carbonate (319.8 mmol) and tetrakistriphenylphosphine palladium (1.1 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 39.9 g of compound 1-G. (Yield 86%, MS[M+H] ⁺ = 435)

Preparation Example 1-8: Synthesis of Compound 1-H

Synthesis of Compound 1-G, except that naphtho[2,1-b]benzofuran-10-ylboronic acid was used instead of naphtho[1,2-b]benzofuran-5-ylboronic acid Compound 1-H 40.3g was obtained by the same method as the method. (Yield 87%, MS[M+H] ⁺ = 435)

Preparation Example 1-9: Synthesis of Compound 1-I

Synthesis of Compound 1-G, except that naphtho[2,3-b]benzofuran-4-ylboronic acid was used instead of naphtho[1,2-b]benzofuran-5-ylboronic acid Compound 1-I 39.4g was obtained by the same method as the method. (Yield 85%, MS[M+H] ⁺ = 435)

Preparation Example 1-10: Synthesis of Compound 1-J

Except that (3-(naphtho[1,2-b]benzofuran-5-yl)phenyl)boronic acid was used instead of naphtho[1,2-b]benzofuran-5-ylboronic acid. , Compound 1-J 47.4g was obtained in the same manner as the synthesis method of compound 1-G. (Yield 87%, MS[M+H] ⁺ = 511)

Preparation Example 1-11: Synthesis of Compound 1-K

Except that (3-(naphtho[2,1-b]benzofuran-10-yl)phenyl)boronic acid was used instead of naphtho[1,2-b]benzofuran-5-ylboronic acid. , Compound 1-K 45.8g was obtained in the same manner as the synthesis method of compound 1-G. (Yield 84%, MS[M+H] ⁺ = 511)

Preparation Example 1-12: Synthesis of Compound 1-L

Except that (4-(naphtho[2,3-b]benzofuran-4-yl)phenyl)boronic acid was used instead of naphtho[1,2-b]benzofuran-5-ylboronic acid. , Compound 1-L 46.8g was obtained by the same method as the synthesis method of compound 1-G. (Yield 86%, MS[M+H] ⁺ = 511)

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

Compound 1-A 12.6 g (30 mmol), bis (pinacolato) diboron (Bis (pinacolato) diboron) 33 mmol, potassium acetate 90 mmol and 1,4-dioxane 130 mL were mixed and heated to 100 °C. 1mmol% of palladium acetate was added thereto, and the mixture was stirred for 12 hours in a reflux state. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified by column chromatography with chloroform/hexane to obtain 13.5 g of compound 2-A. (Yield 88%, MS[M+H] ⁺ = 511)

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

13.8 g of compound 2-B was obtained in the same manner as the synthesis method of compound 2-A, except that compound 1-B was used instead of compound 1-A. (Yield 90%, MS[M+H] ⁺ = 511)

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

13.3 g of compound 2-C was obtained in the same manner as the synthesis method of compound 2-A, except that compound 1-C was used instead of compound 1-A. (Yield 87%, MS[M+H] ⁺ = 511)

Preparation Example 2-4: Synthesis of Compound 2-D

14.6g of compound 2-D was obtained by the same method as the synthesis method of compound 2-A, except that compound 1-D was used instead of compound 1-A. (Yield 83%, MS[M+H] ⁺ = 587)

Preparation Example 2-5: Synthesis of Compound 2-E

14.2 g of compound 2-E was obtained in the same manner as the synthesis method of compound 2-A, except that compound 1-E was used instead of compound 1-A. (Yield 81%, MS[M+H] ⁺ = 587)

Preparation Example 2-6: Synthesis of Compound 2-F

14.6g of compound 2-F was obtained by the same method as the synthesis method of compound 2-A, except that compound 1-F was used instead of compound 1-A. (Yield 83%, MS[M+H] ⁺ = 587)

Preparation Example 2-7: Synthesis of Compound 2-G

13.4 g of compound 2-G was obtained in the same manner as the synthesis method of compound 2-A, except that compound 1-G was used instead of compound 1-A. (Yield 85%, MS[M+H] ⁺ = 527)

Preparation Example 2-8: Synthesis of Compound 2-H

12.9 g of compound 2-H was obtained by the same method as the synthesis method of compound 2-A, except that compound 1-H was used instead of compound 1-A. (Yield 82%, MS[M+H] ⁺ = 527)

Preparation Example 2-9: Synthesis of Compound 2-I

12.6 g of compound 2-I was obtained in the same manner as the synthesis method of compound 2-A, except that compound 1-I was used instead of compound 1-A. (Yield 80%, MS[M+H] ⁺ = 527)

Preparation Example 2-10: Synthesis of Compound 2-J

14.8g of compound 2-J was obtained by the same method as the synthesis method of compound 2-A, except that compound 1-J was used instead of compound 1-A. (Yield 82%, MS[M+H] ⁺ = 603)

Preparation Example 2-11: Synthesis of Compound 2-K

14.6g of compound 2-K was obtained by the same method as the synthesis method of compound 2-A, except that compound 1-K was used instead of compound 1-A. (Yield 81%, MS[M+H] ⁺ = 603)

Preparation Example 2-12: Synthesis of Compound 2-L

15.2 g of compound 2-L was obtained by the same method as the synthesis method of compound 2-A, except that compound 1-L was used instead of compound 1-A. (Yield 84%, MS[M+H] ⁺ = 603)

Preparation Example 3-1: Synthesis of Compound 1

Compound 2-A 10.2 g (20 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine 20 mmol, 1,4-dioxane 80 mL, and water 40 mL were mixed and heated to 60°C. Potassium phosphate (60 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 9.7 g of compound 1. (Yield 79%, MS[M+H] ⁺ = 616)

Preparation Example 3-2: Synthesis of Compound 2

Except that compound 2-B (20mmol) was used instead of compound 2-A, 10 g of compound 2 was obtained in the same manner as the synthesis method of compound 1. (Yield 81%, MS[M+H] ⁺ = 616)

Preparation Example 3-3: Synthesis of Compound 3

10.3 g of compound 3 was obtained by the same method as the synthesis method of compound 1, except that compound 2-C (20 mmol) was used instead of compound 2-A. (Yield 84%, MS[M+H] ⁺ = 616)

Preparation Example 3-4: Synthesis of Compound 4

11 g of compound 4 was obtained by the same method as the synthesis method of compound 1, except that compound 2-D (20 mmol) was used instead of compound 2-A. (Yield 80%, MS[M+H] ⁺ = 692)

Preparation Example 3-5: Synthesis of Compound 5

10.6 g of compound 5 was obtained by the same method as the synthesis method of compound 1, except that compound 2-E (20 mmol) was used instead of compound 2-A. (Yield 77%, MS[M+H] ⁺ = 692)

Preparation Example 3-6: Synthesis of Compound 6

10.8 g of compound 6 was obtained in the same manner as in the synthesis method of compound 1, except that compound 2-F (20 mmol) was used instead of compound 2-A. (Yield 78%, MS[M+H] ⁺ = 692)

Preparation Example 3-7: Synthesis of Compound 7

Compound 2-A 10.2g (20mmol), 2-(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine 20mmol, 1,4-dioxane 80mL and water 40mL were mixed and 60 ℃ Heated to. Potassium phosphate (60 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 recrystallized twice with chloroform and hexane to obtain 10.1 g of compound 7. (Yield 73%, MS[M+H] ⁺ = 692)

Preparation Example 3-8: Synthesis of Compound 8

10.4 g of compound 8 was obtained by the same method as the synthesis method of compound 7 except that compound 2-B (20 mmol) was used instead of compound 2-A. (Yield 75%, MS[M+H] ⁺ = 692)

Preparation Example 3-9: Synthesis of Compound 9

Compound 2-C 10.2g (20mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 20mmol, 1,4-dioxane 80mL and 40mL of water were mixed and 60℃ Heated to. Potassium phosphate (60 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 recrystallized twice with chloroform and hexane to obtain 10 g of compound 9 (yield 72%, MS[M+H] ⁺ = 692)

Preparation Example 3-10: Synthesis of Compound 10

Except for using compound 2-G (20 mmol) instead of compound 2-A, 9.7 g of compound 10 was obtained by the same method as the synthesis method of compound 1. (Yield 77%, MS[M+H] ⁺ = 632)

Preparation Example 3-11: Synthesis of Compound 11

Except for using compound 2-H (20 mmol) instead of compound 2-A, 9.5 g of compound 11 was obtained by the same method as the synthesis method of compound 1. (Yield 75%, MS[M+H] ⁺ = 632)

Preparation Example 3-12: Synthesis of Compound 12

Except for using compound 2-I (20 mmol) instead of compound 2-A, 9.2 g of compound 12 was obtained in the same manner as in the synthesis method of compound 1. (Yield 73%, MS[M+H] ⁺ = 632)

Preparation Example 3-13: Synthesis of Compound 13

10.7 g of compound 13 was obtained in the same manner as the synthesis method of compound 1, except that compound 2-J (20 mmol) was used instead of compound 2-A. (Yield 76%, MS[M+H] ⁺ = 708)

Preparation Example 3-14: Synthesis of Compound 14

11.2 g of compound 14 was obtained by the same method as the synthesis method of compound 1, except that compound 2-K (20 mmol) was used instead of compound 2-A. (Yield 79%, MS[M+H] ⁺ = 708)

Preparation Example 3-15: Synthesis of Compound 15

10.9 g of compound 15 was obtained in the same manner as the synthesis method of compound 1, except that compound 2-L (20 mmol) was used instead of compound 2-A. (Yield 77%, MS[M+H] ⁺ = 708)

Preparation Example 3-16: Synthesis of Compound 16

10.3 g of compound 16 was obtained in the same manner as the synthesis method of compound 7 except that compound 2-G (20 mmol) was used instead of compound 2-A. (Yield 73%, [M+H] ⁺ = 708)

Preparation Example 3-17: Synthesis of Compound 17

Except that compound 2-H (20mmol) was used instead of compound 2-A, 10 g of compound 17 was obtained in the same manner as the synthesis method of compound 7. (Yield 71%, MS[M+H] ⁺ = 708)

Preparation Example 3-18: Synthesis of Compound 18

10.3 g of compound 18 was obtained in the same manner as in the synthesis method of compound 9, except that compound 2-I (20 mmol) was used instead of compound 2-C. (Yield 73%, MS[M+H] ⁺ = 708)

<Example 1-1>

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 100 nm 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 washing 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 prepared ITO transparent electrode with a vacuum degree of 5.0 × 10 ^-4 Pa by vacuum deposition. First, hexanitrile hexaazatriphenylene (HAT-CN) was thermally vacuum deposited to a thickness of 50 nm on ITO to form a hole injection layer.

A hole transport layer (30 nm) was formed by vacuum deposition of 4-4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), which is a material for transporting holes, on the hole injection layer.

On the hole transport layer, N-([1,1'-bisphenyl]-4-yl)-N-(4-(11-([1,1'-biphenyl]-4-yl)-11H-benzo[ a]carbazole-5-yl)phenyl)-[1,1'-biphenyl]-4-amine (EB1) (10 nm) was vacuum deposited to form a hole control layer.

Subsequently, compound 1 and 4CzIPN were vacuum-deposited at a weight ratio of 70:30 on the hole control layer to form a light emitting layer (30 nm). (Compound 4CzIPN's ΔE _ST (difference between singlet energy and triplet energy) is less than 0.2 eV.)

Compound HB1 was vacuum-deposited on the emission layer with a thickness of 10 nm to form an electron control layer.

Compound ET1 and compound LiQ (Lithium Quinolate) were vacuum-deposited at a weight ratio of 1:1 on the electron controlling layer to form an electron injection and transport layer with a thickness of 30 nm. Lithium fluoride (LiF) at a thickness of 1.2 nm and aluminum at a thickness of 200 nm 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 0.04 nm/sec to 0.07 nm/sec, the deposition rate of lithium fluoride was 0.03 nm/sec, and the deposition rate of aluminum was 0.2 nm/sec. Maintaining 10 ^-7 torr to 5 × 10 ^-6 torr, an organic light emitting device was manufactured.

<Examples 1-2 to 1-18>

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

<Comparative Examples 1-1 to 1-3>

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

A current was applied to the organic light-emitting devices manufactured according to Experimental Examples 1-1 to 1-18 and Comparative Examples 1-1 to 1-3 to obtain the results shown in Table 1 below. In Table 1, the color coordinate refers to the CIE color coordinate measured under a current density of 10mA/cm ² .

division compound Voltage
(V@10mA/cm ² ) efficiency
(cd/A@10mA/cm ² ) Color coordinates
(x,y) Example 1-1 One 4.0 21 (0.34, 0.63) Example 1-2 2 4.1 20 (0.33, 0.63) Example 1-3 3 3.9 20 (0.33, 0.62) Example 1-4 4 4.0 22 (0.34, 0.62) Example 1-5 5 4.1 21 (0.34, 0.61) Example 1-6 6 4.1 21 (0.33, 0.62) Example 1-7 7 3.9 22 (0.33, 0.63) Example 1-8 8 4.0 20 (0.34, 0.62) Example 1-9 9 4.1 21 (0.34, 0.63) Example 1-10 10 3.9 20 (0.34, 0.61) Example 1-11 11 4.0 20 (0.34, 0.62) Example 1-12 12 4.0 21 (0.34, 0.63) Example 1-13 13 4.1 22 (0.33, 0.63) Example 1-14 14 4.1 21 (0.33, 0.61) Example 1-15 15 3.9 20 (0.34, 0.61) Example 1-16 16 4.0 22 (0.34, 0.62) Example 1-17 17 4.0 20 (0.34, 0.63) Example 1-18 18 4.1 21 (0.33, 0.63) Comparative Example 1-1 m-CBP 4.7 16 (0.34, 0.62) Comparative Example 1-2 GH3 4.7 16 (0.34, 0.60) Comparative Example 1-3 GH4 4.8 15 (0.34, 0.61)

As shown in Table 1, the devices of Examples 1-1 to 1-18 using the compound of Formula 1 have lower voltage and improved efficiency than the device of Comparative Example 1-1 using the compound m-CBP. I got the result.

In addition, comparing the device using the compound of Formula 1 herein with Comparative Examples 1-2 and 1-3, the compound of m1+m2=1 in Formula 1 of the present invention is m1+m2=0 or m1+m2=2 It can be seen that both the voltage and efficiency characteristics of the device are superior to that of the phosphorus compound.

It was confirmed that the compound of Formula 1 according to the present invention has excellent ability to transfer electrons and holes to a dopant and is applicable to a delayed fluorescence organic light-emitting device.

<Example 2-1>

First host; A second host that is a compound of Formula 1 according to an exemplary embodiment of the present specification; And a compound GD-1 having phosphorescent properties to form an emission layer to manufacture an organic light-emitting device.

A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 130 nm was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. 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.

A hole injection layer was formed by thermally vacuum evaporating the compound HAT-CN to a thickness of 5 nm on the ITO transparent electrode prepared as described above. The compound NPB was thermally vacuum-deposited to a thickness of 80 nm on the hole injection layer to form a first hole transport layer, and compound HT-3 was sequentially vacuum-deposited to a thickness of 50 nm to form a second hole transport layer.

Subsequently, on the second hole transport layer, compound GH-1, compound 1, and compound GD-1 as a phosphorescent dopant were vacuum-deposited at a weight ratio of 47.5:47.5:5 to form a light emitting layer having a thickness of 40 nm.

Compound ET-3 was vacuum-deposited on the emission layer to a thickness of 5 nm to form an electron controlling layer, and compounds ET-4 and LiQ were vacuum-deposited on the electron controlling layer at a weight ratio of 1:1 to form an electron injection and transport layer of 25 nm. Formed. Lithium fluoride (LiF) having a thickness of 1 nm was sequentially deposited on the electron injection and transport layer, and aluminum was deposited thereon to a thickness of 100 nm to form a cathode.

In the above process, the deposition rate of organic material was maintained at 0.04 nm/sec to 0.07 nm/sec, the deposition rate of lithium fluoride was 0.03 nm/sec, and the deposition rate of aluminum was 0.2 nm/sec. Maintained 10 ^-7 torr to 5 × 10 ^-6 torr.

<Examples 2-2 to 2-18>

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that the compound of Table 2 below was used instead of Compound 1 in Example 2-1.

<Comparative Examples 2-1 to 2-3>

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that the following compounds GH-2 to GH-4 were used instead of Compound 1 in Example 2-1.

A current was applied to the organic light emitting devices fabricated in Examples 2-1 to 2-18 and Comparative Examples 2-1 to 2-3 to obtain the results shown in Table 2 below. In Table 2, the color coordinate refers to the CIE color coordinate measured under a current density of 10mA/cm ² .

division compound
(Luminescent layer) Voltage
(V@10mA/cm ² ) efficiency
(cd/A@10mA/cm ² ) Color coordinates
(x,y) Example 2-1 One 3.9 21 (0.33, 0.64) Example 2-2 2 3.9 22 (0.34, 0.64) Example 2-3 3 3.8 21 (0.34, 0.63) Example 2-4 4 4.0 23 (0.33, 0.64) Example 2-5 5 3.9 21 (0.34, 0.63) Example 2-6 6 3.9 21 (0.33, 0.63) Example 2-7 7 3.8 22 (0.34, 0.64) Example 2-8 8 4.0 23 (0.33, 0.64) Example 2-9 9 3.9 22 (0.33, 0.63) Example 2-10 10 4.0 21 (0.34, 0.64) Example 2-11 11 4.0 23 (0.33, 0.64) Example 2-12 12 3.9 22 (0.33, 0.64) Example 2-13 13 3.9 22 (0.34, 0.64) Example 2-14 14 4.0 23 (0.34, 0.63) Example 2-15 15 4.0 21 (0.34, 0.64) Example 2-16 16 3.9 23 (0.33, 0.64) Example 2-17 17 3.8 22 (0.34, 0.64) Example 2-18 18 3.9 21 (0.34, 0.63) Comparative Example 2-1 GH-2 4.4 17 (0.34, 0.63) Comparative Example 2-2 GH-3 4.4 17 (0.34, 0.62) Comparative Example 2-3 GH-4 4.5 15 (0.33, 0.61)

As shown in Table 2, all of the devices of Examples 2-1 to 2-18 using the compound of Formula 1 have lower voltage and improved efficiency than the device of Comparative Example 2-1 using the compound GH-2. I got the result.

In addition, comparing the device using the compound of Formula 1 herein with Comparative Examples 2-2 and 2-3, the compound of m1+m2=1 in Formula 1 of the present invention is m1+m2=0 or m1+m2=2 It can be seen that both the voltage and efficiency characteristics of the device are superior to that of the phosphorus compound.

It was confirmed that the compound of Formula 1 according to the present invention has excellent ability to transfer electrons and holes to a dopant and is applicable to a green phosphorescent organic light-emitting device.

Although preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and detailed description of the invention, and this also belongs to the scope of the invention. .

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

Claims (15)

Compound represented by the following formula (6):
[Formula 6]

In Formula 6,
X is O, S or Se,
L1 and L2 are the same as or different from each other, and each independently an arylene group,
Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group,
m1 and m2 are each independently 0 or 1, and the sum of m1 and m2 is 1,
n1 is an integer of 0 to 4, and when n1 is 2 or more, L1 is the same as or different from each other,
n2 is an integer of 0 to 4, and when n2 is 2 or more, L2 is the same as or different from each other. delete delete delete delete delete delete delete The compound of claim 1, wherein Ar1 and Ar2 are each a phenyl group. The compound of claim 1, wherein the compound represented by Formula 6 is any one selected from the following compounds:

. An organic light-emitting device comprising a first electrode, a second electrode, and at least one organic material layer provided between the first electrode and the second electrode, wherein the organic material layer is a chemical formula according to any one of claims 1, 9, and 10. An organic light-emitting device comprising a compound represented by 6. The method of claim 11, wherein the organic material layer includes an electron injection layer, an electron transport layer, a layer for simultaneously injecting and transporting electrons, or an electron controlling layer, and the electron injection layer, an electron transport layer, a layer for simultaneously injecting and transporting electrons, or an electron controlling layer The organic light emitting diode layer includes the compound represented by Chemical Formula 6. The organic light-emitting device of claim 11, wherein the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 6. The organic light-emitting device of claim 13, wherein the emission layer further includes a host material. The method according to claim 11, wherein the organic material layer comprises a hole injection layer, a hole transport layer, a layer for simultaneously transporting and injecting holes, or a layer for controlling holes, and the hole injection layer, a hole transport layer, a layer for simultaneously transporting and injecting holes, or controlling holes The organic light emitting diode layer includes the compound represented by Chemical Formula 6.

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