CN107973786B - Novel compound and organic light-emitting element using same - Google Patents

Abstract

The present invention provides a compound represented by chemical formula 1 and an organic light emitting element using the same. In the formula, X₁Is O or S, Y₁To Y₃Is N or CR₃，Y₁To Y₃Is N, L₁And L₂Is a bond, C_6‑60Arylene radicals or C_2‑60Heteroarylene radical, Ar₁And Ar₂Is C_6‑60Aryl or C_2‑60Heteroaryl group, Ar₃Is N (Ar)₁₁)(Ar₁₂) Or C_2‑60Heteroaryl, with L₂The bound atom being a hetero atom, Ar₁₁And Ar₁₂Is C_6‑60Aryl or C_2‑60Heteroaryl radical, R₁To R₃Is hydrogen, deuterium, halogen, cyano, amino, C_1‑60Alkyl radical, C_1‑60Haloalkyl, C_1‑60Alkoxy radical, C_1‑60Haloalkoxy, C_3‑60Cycloalkyl radical, C_2‑60Alkenyl radical, C_6‑60Aryl radical, C_6‑60Aryloxy radical or C_2‑60Heterocyclyl, a1 and a2 are integers from 0 to 3. Chemical formula 1

Description

Novel compound and organic light-emitting element using same

Technical Field

Cross reference to related applications

The present application claims priority based on korean patent application No. 10-2016-0139260, 25/10/2016 and korean patent application No. 10-2017-0128262, 29/9/2017, 2016, the entire contents of which are incorporated herein by reference.

The present invention relates to a novel compound and an organic light emitting element including the same.

Background

In general, the organic light emission phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic substance. An organic light emitting element using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research has been conducted.

An organic light-emitting element generally has a structure including an anode and a cathode, and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting element, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With such a structure of the organic light emitting element, if a voltage is applied between two electrodes, holes are injected from an anode into an organic layer, electrons are injected from a cathode into the organic layer, an exciton (exiton) is formed when the injected holes and electrons meet, and light is emitted when the exciton falls back to a ground state.

For organic materials used in the organic light emitting devices described above, development of new materials is continuously demanded.

Disclosure of Invention

The present invention relates to a novel compound and an organic light emitting element including the same.

The present invention provides a compound represented by the following chemical formula 1:

[ chemical formula 1]

In the chemical formula 1 described above,

X₁is O or S, and is a compound of,

Y₁to Y₃Each independently is N or CR₃，Y₁To Y₃At least one of which is N,

L₁and L₂Each independently is a bond, substituted or unsubstituted C_6-60Arylene, or substituted or unsubstituted C containing one or more heteroatoms selected from O, N, Si and S_2-60A hetero-arylene group,

Ar₁and Ar₂Each independently is substituted or unsubstituted C_6-60Aryl, or substituted or unsubstituted C containing 1 to 3 heteroatoms selected from N, O and S_2-60(ii) a heteroaryl group, wherein,

Ar₃is N (Ar)₁₁)(Ar₁₂) Or substituted or unsubstituted C containing 1 to 3 heteroatoms selected from N, O and S_2-60Heteroaryl with the above-mentioned L₂The bonded atoms are heteroatoms such as, for example,

wherein Ar is₁₁And Ar₁₂Each independently is substituted or unsubstituted C_6-60Aryl, or substituted or unsubstituted C containing 1 to 3 heteroatoms selected from N, O and S_2-60(ii) a heteroaryl group, wherein,

R₁to R₃Each independently hydrogen, deuterium, halogen, cyano, amino, substituted or unsubstituted C_1-60Alkyl radical, C_1-60Haloalkyl, substituted or unsubstituted C_1-60Alkoxy, substituted or unsubstituted C_1-60Haloalkoxy, substituted or unsubstituted C_3-60Cycloalkyl, substituted or unsubstituted C_2-60Alkenyl, substituted or unsubstituted C_6-60Aryl, substituted or unsubstituted C_6-60Aryloxy, or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S_2-60A heterocyclic group,

a1 and a2 are each independently an integer from 0 to 3.

In addition, the present invention provides an organic light emitting element including: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include a compound represented by the chemical formula 1.

The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting element, thereby enabling improvement of efficiency, low driving voltage, and/or lifetime characteristics in the organic light emitting element. In particular, the compound represented by the above chemical formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.

Drawings

Fig. 1 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

Fig. 2 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4.

Drawings

1: substrate 2: anode

3: light-emitting layer 4: cathode electrode

5: hole injection layer 6: hole transport layer

7: light-emitting layer 8: an electron transport layer.

Detailed Description

Hereinafter, the present invention will be described in more detail to assist understanding thereof.

In the context of the present specification,

represents a bond to another substituent, and a single bond means that no other atom is present in the moiety represented by L.

The term "substituted or unsubstituted" in the present specification means a compound selected from deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphinoxide group, an alkoxy group, an aryloxy group, an alkylthio group(s) ((R))

Alkyl thio), arylthio(s) ((R)

Aryl thio), alkyl sulfoxide group(s) ((s)

Alkyl sulfonyl), aryl sulfoxide group(s) ((s)

Aryl sulfo xy), silyl, boryl, alkyl, cycloalkyl, alkenyl, Aryl, aralkylThe substituent group may be one or more substituents selected from an alkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a heterocyclic group containing one or more atoms selected from N, O and S, or may be one or more substituents formed by connecting 2 or more substituents selected from the above-mentioned substituents. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, as for the ester group, an oxygen atom in the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be represented by the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

In the present specification, the boron group includes specifically a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group and the like, but is not limited thereto.

In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine, or iodine.

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 one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a2, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadiene, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (diphenylen-1-yl) ethen-1-yl, stilbenyl, and styryl.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,

And a fluorenyl group, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above-mentioned fluorenyl group is substituted, it may be

And the like. But is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,

Azolyl group,

Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl

Examples of the heterocyclic group include, but are not limited to, an azole group, a thiadiazole group, a phenothiazine group, and a dibenzofuran group.

In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group is the same as the above-mentioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned examples of the alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above-mentioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned examples of the alkenyl group. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, the heteroarylene group is a 2-valent group, and in addition to this, the above description about the heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group, and is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic group is not a 1-valent group, and is formed by combining 2 substituents, and in addition to this, the above description of the heterocyclic group can be applied.

In addition, the present invention provides a compound represented by the above chemical formula 1.

In the chemical formula 1 described above,

Y₁and Y₂Is N, Y₃Is CR₃(ii) a Or

Y₁And Y₃Is N, Y₂Is CR₃(ii) a Or

Y₁、Y₂And Y₃May be N.

For example,

Y₁and Y₂Is N, Y₃Is CH; or

Y₁And Y₃Is N, Y₂Is CH; or

Y₁、Y₂And Y₃May be N.

In addition, L₁And L₂Each independently may be a bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

For example, L₁And L₂Each independently may be a bond, or any one selected from the following groups:

specifically, for example, L₁And L₂Each independently may be a bond, or any one selected from the following groups:

in addition, Ar₁And Ar₂Each independently may be any one selected from the following groups:

in the above-mentioned description,

Z₁and Z₂Each independently isHydrogen, deuterium, halogen radical, cyano, amino, C_1-20Alkyl radical, C_1-20Haloalkyl, or C_6-20An aryl group, a heteroaryl group,

c1 and c2 are each independently an integer from 0 to 3. .

Wherein Z is₁And Z₂Each independently may be hydrogen, or phenyl, and c1 and c2 each independently may be 0 or 1.

For example, Ar₁And Ar₂Each independently may be any one selected from the following groups:

in addition, Ar₃Is N (Ar)₁₁)(Ar₁₂) Or substituted or unsubstituted C containing 1 to 3 heteroatoms selected from N, O and S_2-60Heteroaryl with the above-mentioned L₂The bonded atom may be a heteroatom, and more specifically, may be N.

More specifically, Ar is₃May be any one selected from the following groups:

in the above-mentioned groups, the compounds of formula,

X₂and X₃Each independently is O, S, NZ₁₃Or CZ₁₄Z₁₅，

Ar₁₁And Ar₁₂Each independently is substituted or unsubstituted C_6-20Aryl, or substituted or unsubstituted C containing 1 to 3 heteroatoms selected from N, O and S_2-20(ii) a heteroaryl group, wherein,

Z₁₁to Z₁₅Each independently is hydrogen, deuterium, halogen, cyano, amino, C_1-20Alkyl radical, C_1-20Haloalkyl, or C_6-20An aryl group, a heteroaryl group,

n1 and n2 are each independently an integer from 0 to 3.

Wherein Ar is₁₁And Ar₁₂Is phenyl, Z₁₁To Z₁₅Each independently can be hydrogen, methyl, or phenyl, and n1 and n2 each independently can be 0 or 1.

For example, Ar₃May be any one selected from the following groups:

in addition, R₁To R₃Each independently may be hydrogen, deuterium, a halogen group, cyano, amino, methyl, or phenyl, and each independently a1 and a2 may be 0 or 1.

For example, R₁To R₃May be hydrogen.

In this case, a1 represents R₁When a1 is 2 or more, 2 or more R₁May be the same or different from each other. The descriptions of a2, c1, c2, n1, and n2 can be understood with reference to the description of a1 above and the structure of the above formula.

Further, the compound may be any one selected from the following compounds:

the compound represented by the above chemical formula 1 has a structure in which a 6-membered heterocyclic group containing one or more N atoms and the Ar3 substituent described above are connected to a specific position of the core of dibenzofuran or dibenzothiophene, and thus an organic light-emitting element using the compound can have high efficiency, low driving voltage, high luminance, long life, and the like.

The compound represented by the above chemical formula 1 can be produced, for example, by a production method of the following reaction formula. The above-described manufacturing method can be further embodied in the manufacturing examples described later.

[ reaction formula 1]

In the above-mentioned reaction formula 1,

a and E are each independently a halogen group such as chlorine, bromine or the like,

d is a boron (B) -containing organic group such as a boronic acid group, a boronic ester group, or a boronic acid pinacol ester group,

X₁、Y₁to Y₃、L₁、L₂、R₁、R₂、a₁And a₂Is as defined above.

Specifically, the compound (I) of chemical formula 1 can be produced by the following production method. The manufacturing method comprises the following steps: a step (S1) of subjecting the organoboron compound (II) to a suzuki coupling reaction with the halide (III) in the presence of a base and a palladium-based catalyst to produce a compound of formula (IV); and a step (S2) of reacting the compound of formula (IV) with the compound of formula (V).

In the step (S1) for producing the compound of formula (IV), sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, or the like may be used as the base, and tetrakis (triphenylphosphine) palladium (Pd (PPH) may be used as the palladium-based catalyst₃)₄) Palladium acetate, and the like. The reaction can be carried out in an organic solvent such as Tetrahydrofuran (THF), N-Dimethylformamide (DMF), dimethyl sulfoxide (DMSO), or tolueneAnd (4) applying.

In addition, the Suzuki coupling reaction described above may be carried out at a temperature ranging from 80 ℃ to 120 ℃.

In addition, in the step (S2) for producing the compound of the above formula (I), or further in the presence of, for example, Pd (Pt-Bu)₃)₂(Bis (tri-tert-butylphosphine) palladium (0), Bis (tri-tert-butylphosphine) palladium (0)) and the like [ M (Pt-Bu)₃)₂]In the presence of a catalyst of (M ═ Pd, Pt), in a nonpolar solvent such as xylene. In addition, in the above reaction, a base may be added, specifically, a non-nucleophilic base such as NaOt-Bu (Sodium tert-butoxide).

Referring to the structures of reaction formula 1 and chemical formula 1, the organometallic compound (I) represented by chemical formula 1 to be produced can be produced by appropriately substituting the compound (II) and the compound (III) as starting materials and the compound (V).

In addition, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting element, comprising: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include a compound represented by the following chemical formula 1.

The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light-emitting element is not limited to this, and a smaller number of organic layers may be included.

The organic layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or the layer that simultaneously injects and transports holes may include the compound represented by chemical formula 1.

In addition, the organic layer may include a light emitting layer, and the light emitting layer may include the compound represented by chemical formula 1.

The electron transport layer, the electron injection layer, or the layer that simultaneously transports and injects electrons may include the compound represented by chemical formula 1.

In addition, the organic layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include the compound represented by chemical formula 1.

The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure including, as an organic layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode, in addition to the light-emitting layer. However, the structure of the organic light emitting element is not limited thereto, and fewer or more organic layers may be included.

The organic light-emitting element of the present invention may be an organic light-emitting element having a structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate (normal type). The organic light-emitting device of the present invention may be an inverted (inverted) type organic light-emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, fig. 1 and 2 show an example of the structure of the organic light emitting device according to the embodiment of the present invention.

Fig. 1 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In this structure, the compound represented by the above chemical formula 1 may be contained in the above light emitting layer.

Fig. 2 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4. In this structure, the compound represented by the above chemical formula 1 may be contained in 1 or more layers selected from the above hole injection layer, hole transport layer, light emitting layer and electron transport layer.

The organic light-emitting device according to the present invention can be produced by a material and a method known in the art, except that 1 or more of the organic layers contain the compound represented by chemical formula 1. In the case where the organic light-emitting element includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

For example, the organic light-emitting element of the present invention can be manufactured by stacking a first electrode, an organic layer, and a second electrode in this order on a substrate. In this case, the following production can be performed: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a Physical Vapor Deposition (PVD) method such as sputtering or electron beam evaporation (e-beam evaporation) to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting element.

In addition, the compound represented by chemical formula 1 may be formed into an organic 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, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light-emitting element can be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.

As an example, the first electrode is an anode, and the second electrode is a cathode; or the first electrode is a cathode and the second electrode is an anode.

The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO Al or SNO₂A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.

The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO₂And a multilayer structure material such as Al, but not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: the organic light-emitting device has the ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film formation ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a material having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and a substance having a high quantum efficiency with respect to fluorescence or phosphorescence is preferable. As an example, there is 8-hydroxy-quinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzo (b) is

Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.

The light-emitting layer may contain a host material and a dopant material as described above. The host material may further include an aromatic fused ring derivative, a heterocyclic ring-containing compound, or the like, in addition to the compound represented by chemical formula 1. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds

Pyrimidine derivatives, etc., but are not limited thereto.

More specifically, the following compound (H2) can be used in a mixing ratio of 10:90 to 90:10, more specifically, in a mixing ratio of 40:60 to 60: 40.

As the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, or the like having an arylamine group,

And diindenopyrene (Periflanthene), and the like, as the styrylamine compound, a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and which is substituted or unsubstituted with one or two or more substituents selected from an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport layer is a substance that can favorably receive electrons from the cathode and transfer the electrons to the light-emitting layer, and is preferably a substance having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃The organic radical compound, the hydroxyl brass-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the usual substances having a low work function and accompanying an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium are included in each of the substances, and are associated with an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: has electron transporting ability, electron injection effect from the cathode, excellent electron injection effect for the light-emitting layer or the light-emitting material, prevention of transfer of excitons generated in the light-emitting layer to the hole-injecting layer, and thin film shapeThe forming ability is excellent. Specifically, there are fluorenone, anthraquinone dimethane (Anthraquinodimethane), diphenoquinone, thiopyran dioxide, and,

Azole,

Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives, metal complexes, nitrogen-containing 5-membered ring derivatives, and the like thereof, but are not limited thereto.

Examples of the metal complexes include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.

The organic light-emitting element of the present invention may be of a top emission type, a bottom emission type, or a bidirectional emission type depending on the material used.

The compound represented by chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light-emitting element.

The production of the compound represented by the above chemical formula 1 and the organic light emitting device comprising the same is specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

[ production example ]

Production example 1: synthesis of intermediates A1 and A2 Compounds

(1) Production of intermediate A1

Nitrogen gas2-iodobenzene-1,3-diol (2-iodobenzene-1,3-diol) (100g,0.42mol) and (3-chloro-2-fluorophenyl) boronic acid ((3-chloro-2-fluorophenyl) boronic acid) (81.3g,0.47mol) were dissolved in 1000mL of tetrahydrofuran under an atmosphere in a 2000mL round-bottomed flask, and then an aqueous solution of potassium carbonate (175g,1.27mol) dissolved in 500mL of water was added, followed by Bis (tri-tert-butylphosphine) palladium (0) (Bis (tri-tert-butylphosphine) palladium (0)) (2.17g,4.23mmol), followed by stirring with heating for 1 hour. The temperature was lowered to room temperature, the aqueous layer was separated and removed, and then dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized from hexane, and dried to produce the above intermediate A1(80.2g, yield 79%, MS: [ M + H ]]⁺＝239)。

(2) Production of intermediate A2

Intermediate A1(80.2g,0.33mol) and potassium carbonate (139g,1.01mol) were dissolved in 400mL of N-methyl-2-pyrrolidone, and then stirred with heating for 1 hour. Cooling to normal temperature, and performing reverse precipitation

Into water and filtered. The intermediate A2(53.2g, yield 72%, MS: [ M + H ] was obtained by dissolving the resulting product in methylene chloride completely, washing the resulting product with water, drying the product over anhydrous magnesium sulfate, concentrating the product under reduced pressure, recrystallizing the product with ethanol, and drying the product]⁺＝219)。

Production example 2: synthesis of intermediates A3 and A4 Compounds

(1) Production of intermediate A3

After intermediate A2(53.2g,0.23mol) was dissolved in Acetonitrile (Acetonitrile)75mL, calcium carbonate (47.3g,0.34mol) was dissolved in 100mL of water, and nonafluorobutanesulfonyl fluoride (45.2mL,0.25mol) was slowly added dropwise at 0 ℃ for 25 minutes. Then, the mixture was stirred at room temperature for 3 hours. Filtering after the reaction is finished, completely dissolving in dichloromethane, washing with water, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, recrystallizing with ethanol, and drying to obtain the intermediateForm A3(83.3g, 73% yield MS: [ M + H ]]⁺＝501)。

(2) Production of intermediate A4

Intermediate A3(83.3g,0.17mol), 4,5,5-tetramethyl- [1,3, 2-]Dioxaborane (4,4,5, 5-tetramethyi- [1,3, 2)]-dioxaboralane)(46.5g,0.18mol)、Pd(dppf)Cl₂(1.22g,1.66mmol) KOAc (49.0g,0.50mol) was added to 900mL of bis

Alkane (dioxane), and then stirred under reflux for 10 hours. The temperature is reduced to normal temperature, and then the solvent is decompressed and concentrated. Dissolving the concentrated solution in CHCl completely₃Thereafter, the reaction mixture was washed with water, and the resultant solution was concentrated under reduced pressure and then purified by column chromatography to obtain intermediate A4(95.2g, yield 86%, MS: [ M + H ]]⁺＝329)。

Production example 3: synthesis of intermediate A5 Compound

After intermediate A4(30.0g,0.09mol) and 2-chloro-4, 6-diphenyltriazine (2-chloro-4,6-diphenyl-1,3,5-triazine) (24.4g,0.091mmol) were dissolved in 300mL of tetrahydrofuran, potassium carbonate (37.9g,0.27mol) dissolved in 120mL of water was added, and tetrakis (triphenylphosphine) palladium (1.05g,0.91mmol) was added, followed by stirring with heating for 9 hours. After the temperature was lowered to room temperature, the aqueous layer was separated and removed, followed by drying over anhydrous magnesium sulfate, concentration under reduced pressure, recrystallization from dichlorobenzene (dichlorobenzzene), and drying, thereby producing the above-mentioned intermediate A5(32.1g, yield 81%, MS: [ M + H ]: M + H)]⁺＝433)。

Production example 4: synthesis of intermediate A6 Compound

Intermediate a6 was produced in the same manner as in the production of intermediate a5, except that 2-chloro-4- (dibenzo [ b, d ] furan-4-yl) -6-phenyl-1,3,5-triazine (2-chloro-4- (dibenzo [ b, d ] furan-4-yl) -6-phenyl-1,3,5-triazine) was used instead of 2-chloro-4, 6-diphenyltriazine.

Production example 5: synthesis of intermediate A7 Compound

Intermediate a7 was produced in the same manner as in the production of intermediate a5, except that 2-chloro-4- (dibenzo [ b, d ] furan-1-yl) -6-phenyl-1,3,5-triazine (2-chloro-4- (dibenzo [ b, d ] furan-1-yl) -6-phenyl-1,3,5-triazine) was used instead of 2-chloro-4, 6-diphenyltriazine.

Production example 6: synthesis of intermediate A8 Compound

Intermediate A8 was produced in the same manner as in the production of intermediate a5, except that 2-chloro-4- (dibenzo [ b, d ] furan-2-yl) -6-phenyl-1,3,5-triazine (2-chloro-4- (dibenzo [ b, d ] furan-2-yl) -6-phenyl-1,3,5-triazine) was used instead of 2-chloro-4, 6-diphenyltriazine.

Production example 7: synthesis of intermediate A9 Compound

Intermediate a9 was produced in the same manner as in the production of intermediate a5, except that 2-chloro-4- (dibenzo [ b, d ] furan-3-yl) -6-phenyl-1,3,5-triazine (2-chloro-4- (dibenzo [ b, d ] furan-3-yl) -6-phenyl-1,3,5-triazine) was used instead of 2-chloro-4, 6-diphenyltriazine.

Production example 8: synthesis of intermediate A10 Compound

Intermediate a10 was produced in the same manner as in the production of intermediate a5, except that 2-chloro-4- (dibenzo [ b, d ] thiophen-4-yl) -6-phenyl-1,3,5-triazine (2-chloro-4- (dibenz [ b, d ] thiophen-4-yl) -6-phenyl-1,3,5-triazine) was used instead of 2-chloro-4, 6-diphenyltriazine.

Production example 9: synthesis of intermediate A11 Compound

Intermediate a11 was produced in the same manner as in the production of intermediate a5, except that 2-chloro-4- (dibenzo [ b, d ] thiophen-3-yl) -6-phenyl-1,3,5-triazine (2-chloro-4- (dibenz [ b, d ] thiophen-3-yl) -6-phenyl-1,3,5-triazine) was used instead of 2-chloro-4, 6-diphenyltriazine.

Production example 10: synthesis of intermediate A12 Compound

Intermediate a12 was produced in the same manner as in the production of intermediate a5, except that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2- (4-bromophenyl) -4, 6-diphenyl1, 3,5-triazine) was used in place of 2-chloro-4, 6-diphenyltriazine.

Production example 11: synthesis of intermediate A13 Compound

Intermediate a13 was produced in the same manner as in the production of intermediate a5, except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2- (3-bromophenyl) -4, 6-diphenyl1, 3,5-triazine) was used in place of 2-chloro-4, 6-diphenyltriazine.

Production example 12: synthesis of intermediate A14 Compound

Intermediate a14 was produced in the same manner as intermediate a5 except that 2-chloro-4,6-diphenylpyrimidine (2-chloro-4,6-diphenylpyrimidine) was used instead of 2-chloro-4, 6-diphenyltriazine.

Production example 13: synthesis of intermediate A15 Compound

Intermediate a15 was produced in the same manner as intermediate a5 except that 4-chloro-2,6-diphenylpyrimidine (4-chloro-2, 6-diphenylpyrinidine) was used instead of 2-chloro-4, 6-diphenyltriazine.

[ examples ]

Example 1: synthesis of Compound 1

Under a nitrogen atmosphere, intermediate A5(10.0g,0.023mol) and diphenylamine (3.90g,0.19mol), Bis (tri-tert-butylphosphine) palladium (0) (Bis (tri-tert-butylphosphine) palladium (0)) (0.12g,0.23mmol), sodium tert-butoxide (3.32g,0.035mol) were added to 110ml of xylene, and heated and stirred for 9 hours. Cooling to room temperature, filtering to remove salt, concentrating xylene under reduced pressure, dissolving with dichlorobenzene (dichlorobenzzene), washing with water, and MgSO₄Water was removed and solvent was removed. Then, the compound 1 is produced by recrystallization from N-methyl-2-pyrrolidone. (9.2g, yield 70%, MS: [ M + H ]]⁺＝567)

Example 2: synthesis of Compound 2

Use two([1,1' -Biphenyl)]-4-yl) amine (di ([1,1' -biphenyl)]-4-yl) amine) in place of diphenylamine, compound 2 was produced by the same method as that for producing compound 1. (yield 74%, MS: [ M + H ]]⁺＝719)

Example 3: synthesis of Compound 3

Using N- ([1,1' -biphenyl)]-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (N- ([1,1' -biphenyl)]Compound 3 was produced in the same manner as in the production of Compound 1, except that (E) -4-yl) -9, 9-dimethyl-9H-fluoron-2-amine) was used instead of diphenylamine. (yield 72%, MS: [ M + H ]]⁺＝759)

Example 4: synthesis of Compound 4

Compound 4 was produced by the same method as the method for producing compound 1, except that 9H-carbazole was used instead of diphenylamine. (yield 72%, MS: [ M + H ]]⁺＝565)

Example 5: synthesis of Compound 5

Using 7H-benzo [ c ]]Carbazole (7H-benzol [ c ]]carbazole) was used instead of diphenylamine, and compound 5 was produced by the same method as that for producing compound 1. (yield 77%, MS: [ M + H ]]⁺＝615)

Example 6: synthesis of Compound 6

Using 7,7-dimethyl-5,7-dihydroindeno [2,1-b ]]Carbazole (7),7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole) was used instead of diphenylamine, and compound 6 was produced by the same method as that for producing compound 1. (yield 80%, MS: [ M + H ]]⁺＝681)

Example 7: synthesis of Compound 7

Using 12,12-dimethyl-11,12-dihydroindeno [2,1-a ]]Carbazole (12,12-dimethyl-11,12-dihydroindeno [2,1-a ]]compound 7 was produced by the same method as the method for producing compound 1, except that carbazole was used instead of diphenylamine. (yield 82%, MS: [ M + H ]]⁺＝681)

Example 8: synthesis of Compound 8

Using 11-phenyl-11, 12-dihydroindeno [2,3-a ]]Carbazole (11-phenyl-11,12-dihydroindolo [2, 3-a)]carbazole) was used instead of diphenylamine, and compound 8 was produced by the same method as that for producing compound 1. (yield 82%, MS: [ M + H ]]⁺＝730)

Example 9: synthesis of Compound 9

Using 5-phenyl-5, 12-dihydroindeno [3,2-a ]]Carbazole (5-phenyl-5,12-dihydroindolo [3, 2-a)]carbazole) was used instead of diphenylamine, and compound 9 was produced by the same method as the method for producing compound 1. (yield 79%, MS: [ M + H ]]⁺＝730)

Example 10: synthesis of Compound 10

Compound 10 was produced by the same method as the method for producing compound 1, except that intermediate a6 was used instead of intermediate a 5. (yield 74%, MS: [ M + H ]]⁺＝657)

Example 11: synthesis of Compound 11

Using intermediate A6 and N-phenyl- [1,1' -biphenyl]-4-amine (N-phenyl- [1,1' -biphenyl)]-4-amine) in place of intermediate a5 and diphenylamine, compound 11 was produced by the same method as the method for producing compound 1. (yield 75%, MS: [ M + H ]]⁺＝733)

Example 12: synthesis of Compound 12

Compound 12 was produced by the same method as the method for producing compound 1, except that intermediate a6 and 9H-carbazole were used instead of intermediate a5 and diphenylamine. (yield 77%, MS: [ M + H ]]⁺＝655)

Example 13: synthesis of Compound 13

Using intermediates A6 and 11H-benzo [ a ]]Carbazole (11H-benzol [ a ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 13 was produced by the same method as the method for producing compound 1. (yield 82%, MS: [ M + H ]]⁺＝705)

Example 14: synthesis of Compound 14

Using intermediate A6 and 7,7-dimethyl-5,7-dihydroindeno [2,1-b ]]Carbazole (7,7-dimethyl-5,7-dihydroindeno [2,1-b ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 14 was produced by the same method as the method for producing compound 1. (yield 84%, MS: [ M + H ]]⁺＝771)

Example 15: synthesis of Compound 15

Using intermediate A6 and 12-phenyl-5, 12-indolino [3,2-a ]]Carbazole (12-phenyl-5,12-dihydroindolo [3, 2-a)]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 15 was produced by the same method as the method for producing compound 1. (yield 84%, MS: [ M + H ]]⁺＝820)

Example 16: synthesis of Compound 16

Compound 16 was produced by the same method as the method for producing compound 1, except that intermediate a7 was used instead of intermediate a 5. (yield 71%, MS: [ M + H ]]⁺＝657)

Example 17: synthesis of Compound 17

Using intermediate A7 and N- ([1,1' -biphenyl)]-4-yl) - [1,1' -biphenyl]-3-amine (N- ([1,1' -biphenyl)]-4-yl)-[1,1'-biphenyl]-3-amine) in place of intermediate a5 and diphenylamine, compound 17 was produced by the same method as the method for producing compound 1. (yield 74%, MS: [ M + H ]]⁺＝809)

Example 18: synthesis of Compound 18

Compound 18 was produced by the same method as the method for producing compound 1, except that intermediate a7 and 9H-carbazole were used instead of intermediate a5 and diphenylamine. (yield 77%, MS: [ M + H ]]⁺＝657)

Example 19: synthesis of Compound 19

Using intermediates A7 and 7H-benzo [ c ]]Carbazole (7H-benzol [ c ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 19 was produced by the same method as the method for producing compound 1. (yield 79%, MS: [ M + H ]]⁺＝705)

Example 20: synthesis of Compound 20

Using intermediate A7 and 7,7-dimethyl-5,7-dihydroindeno [2,1-b ]]Carbazole (7,7-dimethyl-5,7-dihydroindeno [2,1-b ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 20 was produced by the same method as the method for producing compound 1. (yield 83%, MS: [ M + H ]]⁺＝771)

Example 21: synthesis of Compound 21

Using intermediate A7 and 5-phenyl-5, 12-dihydroindeno [3,2-a]Carbazole (5-phenyl-5,12-dihydroindolo [3, 2-a)]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 21 was produced by the same method as the method for producing compound 1. (yield 83%, MS: [ M + H ]]⁺＝820)

Example 22: synthesis of Compound 22

Intermediate A8 and bis ([1,1' -biphenyl ] yl)]-4-yl) amine (di ([1,1' -biphenyl)]-4-yl) amine) in place of intermediate a5 and diphenylamine, compound 22 was produced by the same method as the method for producing compound 1. (yield 73%, MS: [ M + H ]]⁺＝809)

Example 23: synthesis of Compound 23

Compound 23 was produced by the same method as the method for producing compound 1, except that intermediate A8 and 9H-carbazole were used instead of intermediate a5 and diphenylamine. (yield 72%, MS: [ M + H ]]⁺＝655)

Example 24: synthesis of Compound 24

Using intermediates A8 and 5H-benzo [ b ]]Carbazole (5H-benzol [ b ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 24 was produced by the same method as the method for producing compound 1. (yield 79%, MS: [ M + H ]]⁺＝705)

Example 25: synthesis of Compound 25

Using intermediate A8 and 7,7-dimethyl-7,12-dihydroindeno [1,2-a ]]Carbazole (7,7-dimethyl-7,12-dihydroindeno [1,2-a ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 25 was produced by the same method as the method for producing compound 1. (yield 79%, MS: [ M + H ]]⁺＝771)

Example 26: synthesis of Compound 26

Using intermediate A8 and 12-phenyl-5, 12-dihydroindeno [3,2-a]Carbazole (12-phenyl-5,12-dihydroindolo [3, 2-a)]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 26 was produced by the same method as the method for producing compound 1. (yield 85%, MS: [ M + H ]]⁺＝820)

Example 27: synthesis of Compound 27

Using intermediates A8 and 13,13-dimethyl-11, 13-dihydrobenzopyrano [3,2-b]Carbazole (13,13-dimethyl-11,13-dihydrochromeno [3,2-b ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 27 was produced by the same method as the method for producing compound 1. (yield 80%, MS: [ M + H ]]⁺＝787)

Example 28: synthesis of Compound 28

Using intermediate A9 and N- ([1,1' -biphenyl)]-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (N- ([1,1' -biphenyl)]Compound 28 was produced by the same method as the method for producing compound 1, except that-4-yl) -9, 9-dimethyl-9H-fluoron-2-amine) was used instead of intermediate a5 and diphenylamine. (yield 77%, MS: [ M + H ]]⁺＝849)

Example 29: synthesis of Compound 29

Using intermediate A9 and 12,12-dimethyl-5,12-Dihydroindeno [1,2-c ]]Carbazole (12,12-dimethyl-5,12-dihydroindeno [1,2-c ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 29 was produced by the same method as the method for producing compound 1. (yield 79%, MS: [ M + H ]]⁺＝771)

Example 30: synthesis of Compound 30

Using intermediate A9 and 12-phenyl-5, 12-dihydroindeno [3,2-a]Carbazole (12-phenyl-5,12-dihydroindolo [3, 2-a)]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 30 was produced by the same method as the method for producing compound 1. (yield 80%, MS: [ M + H ]]⁺＝820)

Example 31: synthesis of Compound 31

Using intermediate A9 and 13,13-dimethyl-7, 13-dihydrobenzopyrano [2,3-b ]]Carbazole (13,13-dimethyl-7,13-dihydrochromeno [2,3-b ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 31 was produced by the same method as the method for producing compound 1. (yield 82%, MS: [ M + H ]]⁺＝787)

Example 32: synthesis of Compound 32

Intermediate A10 and bis ([1,1' -biphenyl ] yl)]-4-yl) amine (di ([1,1' -biphenyl)]-4-yl) amine) was prepared by the same method as the method for preparing compound 1 except that intermediate a5 and diphenylamine were replaced. (yield 73%, MS: [ M + H ]]⁺＝825)

Example 33: synthesis of Compound 33

Using intermediates A10 and 5H-benzo [ b ]]Carbazole (5H-benzol [ b ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 33 was produced by the same method as the method for producing compound 1. (yield 77%, MS: [ M + H ]]⁺＝721)

Example 34: synthesis of Compound 34

Using intermediate A10 and 11,11-dimethyl-5,11-dihydroindeno [1,2-b ]]Carbazole (11,11-dimethyl-5,11-dihydroindeno [1,2-b ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 34 was produced by the same method as the method for producing compound 1. (yield 75%, MS: [ M + H ]]⁺＝787)

Example 35: synthesis of Compound 35

Using intermediate A10 and 5-phenyl-5, 12-dihydroindeno [3,2-a]Carbazole (5-phenyl-5,12-dihydroindolo [3, 2-a)]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 35 was produced by the same method as the method for producing compound 1. (yield 79%, MS: [ M + H ]]⁺＝836)

Example 36: synthesis of Compound 36

Using intermediate A11 and N-phenyl- [1,1' -biphenyl]-4-amine (N-phenyl- [1,1' -biphenyl)]-4-amine) in place of intermediate a5 and diphenylamine, compound 36 was produced by the same method as the method for producing compound 1. (yield 70%, MS: [ M +)H]⁺＝749)

Example 37: synthesis of Compound 37

Compound 37 was produced by the same method as the method for producing compound 1, except that intermediate a11 and 9H-carbazole were used instead of intermediate a5 and diphenylamine. (yield 73%, MS: [ M + H ]]⁺＝671)

Example 38: synthesis of Compound 38

Using intermediate A11 and 7,7-dimethyl-5,7-dihydroindeno [2,1-b ]]Carbazole (7,7-dimethyl-5,7-dihydroindeno [2,1-b ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 38 was produced by the same method as the method for producing compound 1. (yield 76%, MS: [ M + H ]]⁺＝787)

Example 39: synthesis of Compound 39

Using intermediate A11 and 8,8-dimethyl-5,8-dihydroindeno [2,1-c ]]Carbazole (8,8-dimethyl-5,8-dihydroindeno [2, 1-c)]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 39 was produced by the same method as the method for producing compound 1. (yield 79%, MS: [ M + H ]]⁺＝787)

Example 40: synthesis of Compound 40

Using intermediate A11 and 5-phenyl-5, 12-dihydroindeno [3,2-a]Carbazole (5-phenyl-5,12-dihydroindolo [3, 2-a)]carbazole) generationCompound 40 was produced by the same method as the method for producing compound 1, except that intermediate a5 and diphenylamine were replaced. (yield 77%, MS: [ M + H ]]⁺＝836)

Example 41: synthesis of Compound 41

Compound 41 was produced by the same method as the method for producing compound 1, except that intermediate a12 was used instead of intermediate a 5. (yield 69%, MS: [ M + H ]]⁺＝643)

Example 42: synthesis of Compound 42

Using intermediate A12 and N- ([1,1' -biphenyl)]-4-yl) - [1,1' -biphenyl]-3-amine (N- ([1,1' -biphenyl)]-4-yl)-[1,1'-biphenyl]-3-amine) in place of intermediate a5 and diphenylamine, compound 42 was produced by the same method as the method for producing compound 1. (yield 75%, MS: [ M + H ]]⁺＝795)

Example 43: synthesis of Compound 43

Compound 43 was produced by the same method as the method for producing compound 1, except that intermediate a12 and 9H-carbazole were used instead of intermediate a5 and diphenylamine. (yield 74%, MS: [ M + H ]]⁺＝641)

Example 44: synthesis of Compound 44

Using intermediate A12 and 7,7-dimethyl-5,7-dihydroindeno [2,1-b ]]Carbazole (7, 7-di)methyl-5,7-dihydroindeno[2,1-b]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 44 was produced by the same method as the method for producing compound 1. (yield 79%, MS: [ M + H ]]⁺＝757)

Example 45: synthesis of Compound 45

Using intermediate A12 and 5-phenyl-5, 12-dihydroindeno [3,2-a]Carbazole (5-phenyl-5,12-dihydroindolo [3, 2-a)]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 45 was produced by the same method as the method for producing compound 1. (yield 77%, MS: [ M + H ]]⁺＝806)

Example 46: synthesis of Compound 46

Compound 46 was produced by the same method as the method for producing compound 1, except that intermediate a13 was used instead of intermediate a 5. (yield 70%, MS: [ M + H ]]⁺＝643)

Example 47: synthesis of Compound 47

Using intermediate A13 and N- ([1,1' -biphenyl)]-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (N- ([1,1' -biphenyl)]Compound 47 was produced by the same method as the method for producing compound 1, except that-4-yl) -9, 9-dimethyl-9H-fluoron-2-amine) was used instead of intermediate a5 and diphenylamine. (yield 73%, MS: [ M + H ]]⁺＝835)

Example 48: synthesis of Compound 48

Compound 48 was produced by the same method as the method for producing compound 1, except that intermediate a13 and 9H-carbazole were used instead of intermediate a5 and diphenylamine. (yield 75%, MS: [ M + H ]]⁺＝641)

Example 49: synthesis of Compound 49

Using intermediate A13 and 12,12-dimethyl-11,12-dihydroindeno [2,1-a ]]Carbazole (12,12-dimethyl-11,12-dihydroindeno [2,1-a ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 49 was produced by the same method as the method for producing compound 1. (yield 77%, MS: [ M + H ]]⁺＝757)

Example 50: synthesis of Compound 50

Using intermediate A13 and 5-phenyl-5, 7-indolino [2,3-b ]]Carbazole (5-phenyl-5,7-dihydroindolo [2,3-b ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 50 was produced by the same method as the method for producing compound 1. (yield 75%, MS: [ M + H ]]⁺＝806)

Example 51: synthesis of Compound 51

Intermediate A14 and bis ([1,1' -biphenyl ] yl)]-4-yl) amine (di ([1,1' -biphenyl)]-4-yl) amine) in place of intermediate a5 and diphenylamine, compound 51 was produced by the same method as the method for producing compound 1. (yield 70%, MS: [ M + H ]]⁺＝718)

Example 52: synthesis of Compound 52

Compound 52 was produced by the same method as the method for producing compound 1, except that intermediate a14 and 9H-carbazole were used instead of intermediate a5 and diphenylamine. (yield 73%, MS: [ M + H ]]⁺＝564)

Example 53: synthesis of Compound 53

Using intermediates A14 and 7H-benzo [ c ]]Carbazole (7H-benzol [ c ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 53 was produced by the same method as the method for producing compound 1. (yield 72%, MS: [ M + H ]]⁺＝614)

Example 54: synthesis of Compound 54

Using intermediate A14 and 7,7-dimethyl-5,7-dihydroindeno [2,1-b ]]Carbazole (7,7-dimethyl-5,7-dihydroindeno [2,1-b ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 54 was produced by the same method as the method for producing compound 1. (yield 76%, MS: [ M + H ]]⁺＝680)

Example 55: synthesis of Compound 55

Using intermediate A14 and 5-phenyl-5, 12-indolino [3,2-a ]]Carbazole (5-phenyl-5,12-dihydroindolo [3, 2-a)]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 55 was produced by the same method as the method for producing compound 1. (yield 79%, MS: [ M + H ]]⁺＝729)

Example 56: synthesis of Compound 56

Using intermediate A15 and N- ([1,1' -biphenyl)]-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (N- ([1,1' -biphenyl)]Compound 56 was produced by the same method as the method for producing compound 1, except that-4-yl) -9, 9-dimethyl-9H-fluoron-2-amine) was used instead of intermediate a5 and diphenylamine. (yield 73%, MS: [ M + H ]]⁺＝758)

Example 57: synthesis of Compound 57

Compound 57 was produced by the same method as the method for producing compound 1, except that intermediate a15 and 9H-carbazole were used instead of intermediate a5 and diphenylamine. (yield 74%, MS: [ M + H ]]⁺＝564)

Example 58: synthesis of Compound 58

Using intermediate A15 and 12,12-dimethyl-11,12-dihydroindeno [2,1-a ]]Carbazole (12,12-dimethyl-11,12-dihydroindeno [2,1-a ]]carbazole) was used instead of intermediate a5 and diphenylamine, and compound 58 was produced by the same method as the method for producing compound 1. (yield 72%, MS: [ M + H ]]⁺＝680)

Example 59: synthesis of Compound 59

Using intermediate A15 and 5-phenyl-5, 12-indolino [3,2-a ]]Carbazole (5-phenyl-5,12-dihydroindolo [3, 2-a)]carbazole) in place of intermediate a5 and diphenylExcept for the amine, compound 59 was produced by the same method as the method for producing compound 1. (yield 72%, MS: [ M + H ]]⁺＝729)

Experimental example 1

Will be provided with

The glass substrate coated with ITO (indium tin oxide) is put into distilled water dissolved with detergent and washed by ultrasonic wave. In this case, a product of fisher corporation (Fischer Co.) was used as the detergent, and distilled water obtained by filtering 2 times with a Filter (Filter) manufactured by Millipore Co was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating 2 times with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with solvents such as isopropyl alcohol, acetone and methanol, dried and then transferred to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode thus prepared

The following hexanitrile Hexaazatriphenylene (HAT) compound was thermally vacuum-evaporated to form a hole injection layer. On the hole injection layer

By thermal vacuum evaporation of HT1 compound and

the hole transport layer was formed by vacuum vapor deposition of a HT2 compound in this order. Next, on the hole transport layer, compound 1 and compound H2 of example 1 were co-evaporated with the phosphorescent dopant Dp at the weight ratio shown in table 1 as the host, to form a hole transport layer

A thick light emitting layer. On the above-mentioned luminescent layer

ET1 material was vacuum evaporated to form a hole blocking layer. An ET2 substance and LiQ (Lithium quinolinate) were vacuum-deposited on the hole-blocking layer at a weight ratio of 1:1 to form a hole-blocking layer

The electron transport layer of (1). Sequentially evaporating on the electron transport layer

A thickness of lithium fluoride (LiF) on top of it

Aluminum is evaporated to a thickness to form a cathode.

In the above process, the evaporation speed of the organic material is maintained

Sec, maintenance of lithium fluoride at the cathode

Evaporation Rate,/sec, aluminum maintenance

Deposition rate of/sec, vacuum degree maintained at 1X 10 during deposition^-7～5×10^-8torr。

The current was applied to the produced organic light-emitting element, and the voltage, efficiency and lifetime were measured, and the results are shown in table 1 below.

Experimental examples 2 to 16

Organic light-emitting elements of experimental examples 2 to 16 were produced in the same manner as in experimental example 1 except that compounds described in table 1 below were used as phosphorescent dopants in place of compound 1 in example 1. In this case, when a mixture of 2 compounds is used as a host, the brackets indicate the weight ratio between the host compounds, and the H2 substance is the same as described above.

The organic light-emitting element thus produced was subjected to current application in the same manner as in experimental example 1, and the voltage, efficiency and lifetime were measured, and the results are shown in table 1 below.

Comparative Experimental examples 1 to 5

An organic light-emitting device was produced in the same manner as in experimental example 1, except that the compound described in table 1 below was used in the amount described in table 1 instead of the compound 1 in example 1. C1 to C3 in table 1 below represent the following compounds, respectively. In this case, when a mixture of 2 compounds is used as a host, the parentheses indicate the weight ratio between the host compounds.

The organic light-emitting element thus produced was applied with a current by the same method as in experimental example 1, and the voltage, efficiency and lifetime were measured and are shown in table 1 below.

[ TABLE 1]

In table 1 above, T95 represents the time required for the luminance to reach 95% of the initial luminance.

As shown in table 1 above, it was confirmed that the compound according to the present invention is a host substance having more excellent high efficiency and long life characteristics than the compound C1 which is a conventional green light emitting host substance. Further, the compound showed a lifetime characteristic increased by about 2 times or more as compared with compound C2, and a low voltage and a long lifetime characteristic as compared with compound C3. From this, it was confirmed that the compounds of examples have different voltage and lifetime depending on the substitution position of dibenzofuran.

In addition, it was confirmed that triazine as a hetero substituent showed advantages in efficiency and life in comparison with those in comparative examples 3 and 4 when it was located at the position No. 1 of dibenzofuran, and when it was located at the position No. 2. Further, when comparative example 5 is compared with the compound of the present invention, a large voltage difference is exhibited depending on the position of the substituent, which shows an advantage of the element in terms of stability and balance in which holes and electrons from the adjacent layer of the element can be received, structurally when the substituent is located at positions No. 1 and No. 6 of dibenzofuran compared with positions No. 4 and No. 6.

The preferred examples of the present invention have been described above, but the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention, and the scope of the present invention also falls within the scope of the present invention.

Claims (9)

1. A compound represented by the following chemical formula 1:

chemical formula 1

In the chemical formula 1 described above,

X₁is O or S, and is a compound of,

Y₁to Y₃Each independently is N or CR₃，Y₁To Y₃At least one of which is N,

L₁and L₂Each independently is a bond, or is selected from any one of the following groups:

Ar₁and Ar₂Each independently is any one selected from the following groups:

in the above-mentioned groups, the compounds of formula,

Z₁and Z₂Each of which is independently hydrogen, is,

c1 and c2 are each independently an integer of 0 or 1,

Ar₃is any one selected from the following groups:

in the above-mentioned groups, the compounds of formula,

X₂is O, S, NZ₁₃Or CZ₁₄Z₁₅，

Ar₁₁And Ar₁₂Each independently being unsubstituted or substituted by methyl or phenyl_6-20An aryl group, a heteroaryl group,

Z₁₁and Z₁₂Is a hydrogen atom, and is,

Z₁₃is hydrogen or C_6-20An aryl group, a heteroaryl group,

Z₁₄and Z₁₅Each independently is hydrogen or C_1-20An alkyl group, a carboxyl group,

n1 and n2 are each independently an integer from 0 to 3,

R₁to R₃Is a hydrogen atom, and is,

a1 and a2 are each independently an integer from 0 to 3.

2. The compound of claim 1, wherein,

Y₁and Y₂Is N, Y₃Is CH;

Y₁and Y₃Is N, Y₂Is CH; or

Y₁、Y₂And Y₃Is N.

3. The compound of claim 1, wherein Ar₁And Ar₂Each independently is any one selected from the following groups:

4. the compound of claim 1, wherein Ar₃Is any one selected from the following groups:

5. the compound of claim 1, wherein the compound is any one selected from the group consisting of:

6. an organic light-emitting element comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic material layers provided between the first electrode and the second electrode,

1 or more of the organic layers comprise a compound of any one of claims 1 to 5.

7. The organic light-emitting element according to claim 6, wherein the organic layer containing the compound is a hole-injecting layer, a hole-transporting layer, or a layer in which hole injection and hole transport are performed simultaneously.

8. The organic light-emitting element according to claim 6, wherein the organic layer containing the compound is an electron injection layer, an electron transport layer, or a layer in which electron injection and electron transport are performed simultaneously.

9. The organic light-emitting element according to claim 6, wherein the organic layer containing the compound is a light-emitting layer.

Images