阅读说明：本技术 有机化合物、发光元件、发光装置、电子设备及照明装置 (Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device ) 是由 山口知也 吉住英子 木户裕允 渡部智美 渡部刚吉 濑尾哲史 于 2018-06-08 设计创作，主要内容包括：提供一种新颖的有机化合物。尤其是,提供一种能够提高发光元件的元件特性的新颖的有机化合物。此外,提供一种发光效率、驱动电压及可靠性优良的新颖的发光元件。本发明的一个方式是一种具有苯并呋喃并[2,3-b]吡啶骨架或苯并噻吩并[2,3-b]吡啶骨架,在苯并呋喃并[2,3-b]吡啶骨架或苯并噻吩并[2,3-b]吡啶骨架的吡啶环一侧和苯环一侧双方具有至少一个取代基的有机化合物。此外,还提供一种包含该有机化合物的发光元件。该有机化合物特别适用于蓝色磷光元件。(Novel organic compounds are provided. In particular, a novel organic compound which can improve element characteristics of a light-emitting element is provided. Further, a novel light-emitting element excellent in light-emitting efficiency, driving voltage, and reliability is provided. An embodiment of the present invention is an organic compound having a benzofuro [2,3-b ] pyridine skeleton or a benzothieno [2,3-b ] pyridine skeleton, and having at least one substituent on both the pyridine ring side and the benzene ring side of the benzofuro [2,3-b ] pyridine skeleton or the benzothieno [2,3-b ] pyridine skeleton. Further, a light-emitting element including the organic compound is provided. The organic compound is particularly suitable for a blue phosphor element.)

1. An organic compound represented by the following general formula (G0).

(in the general formula (G0), X represents oxygen or sulfur, Ar ¹Represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, R ¹To R ⁵Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, A represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 3 to 30 carbon atoms, n represents an integer of 1 to 4,Ht ¹represents a substituted or unsubstituted fused heteroaromatic ring,

the fused heteroaromatic ring contains any one or more selected from a carbazole skeleton, a dibenzofuran skeleton and a dibenzothiophene skeleton,

the number of carbon atoms of the fused heteroaromatic ring is 12 or more and 30 or less. )

2. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of,

wherein A represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms,

and the aromatic hydrocarbon group having 6 to 30 carbon atoms has at least one condensed ring.

3. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of,

wherein the Ht ¹Is any of the groups represented by the following general formulae (Ht-1) to (Ht-4).

(in the general formulae (Ht-1) to (Ht-4), R ⁹To R ¹⁴Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. R ⁶To R ⁹And/or R ¹⁰To R ¹³Each of which may be bonded to each other to form a saturated ring or an unsaturated ring. )

4. An organic compound represented by the following general formula (G1).

(in the general formula (G1), X represents oxygen or sulfur, Ar ¹And Ar ²Each independently represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, R ¹To R ⁵Are respectively independentRepresents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, n represents an integer of 1 to 4, l represents an integer of 0 to 4, Ht ¹And Ht ²Each independently represents a substituted or unsubstituted fused heteroaromatic ring,

the fused heteroaromatic ring contains any one or more selected from a carbazole skeleton, a dibenzofuran skeleton and a dibenzothiophene skeleton,

the fused heteroaromatic ring has 12 to 30 carbon atoms. )

5. The organic compound according to claim 4, wherein the organic compound is represented by the following general formula (G2).

6. The organic compound according to claim 4, wherein the organic compound is represented by the following general formula (G3).

7. The organic compound according to claim 4, wherein the organic compound is represented by the following general formula (G4).

8. The organic compound according to claim 4, wherein the organic compound is represented by the following general formula (G5).

9. The organic compound according to claim 4, wherein the organic compound is a compound represented by formula (I),

wherein the Ht ¹And the Ht ²Each independently is any one of groups represented by the following general formulae (Ht-1) to (Ht-4).

(in the general formulae (Ht-1) to (Ht-4), R ⁹To R ¹⁴Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. R ⁶To R ⁹And/or R ¹⁰To R ¹³Each of which may be bonded to each other to form a saturated ring or an unsaturated ring. )

10. An organic compound represented by the following general formula (G6).

(in the general formula (G6), X, Z ¹And Z ²Each independently represents oxygen or sulfur. )

11. The organic compound according to claim 10, wherein the organic compound is represented by the following structural formula (100).

12. A light-emitting element using the organic compound according to claim 4.

13. A display device, comprising:

the light-emitting element according to claim 12; and

at least one of a color filter and a transistor.

14. An electronic device, comprising:

the display device of claim 13; and

at least one of the frame and the touch sensor.

15. An illumination device, comprising:

the light-emitting element according to claim 12; and

at least one of the frame and the touch sensor.

Technical Field

One embodiment of the present invention relates to a novel organic compound. In addition, one embodiment of the present invention relates to an organic compound having a benzofuro [2,3-b ] pyridine skeleton or a benzothieno [2,3-b ] pyridine skeleton. Another embodiment of the present invention relates to a light-emitting element, a light-emitting device, an electronic device, and a lighting device each including the organic compound.

Note that one embodiment of the present invention is not limited to the above-described technical field. One embodiment of the invention relates to an object, a method, or a method of manufacture. In addition, the present invention relates to a process (process), machine (machine), product (manufacture) or composition (matter). In particular, one embodiment of the present invention relates to a semiconductor device, a light-emitting device, a display device, an illumination device, a light-emitting element, and methods for manufacturing the same. In addition, one embodiment of the present invention relates to a method for synthesizing a novel organic compound having a benzofuro [2,3-b ] pyridine skeleton or a benzothieno [2,3-b ] pyridine skeleton. Therefore, as an example of one embodiment of the present invention disclosed in the present specification, a light-emitting element, a light-emitting device, an electronic device, and a lighting device each containing the organic compound, and methods for manufacturing the light-emitting element, the light-emitting device, the electronic device, and the lighting device can be given.

Background

In recent years, light-emitting elements (organic EL elements) utilizing Electroluminescence (EL) using organic compounds have been actively put into practical use. In the basic structure of these light-emitting elements, an organic compound layer (EL layer) containing a light-emitting material is interposed between a pair of electrodes. By applying a voltage to the element, carriers are injected, and light emission from the light-emitting material can be obtained by recombination energy of the carriers.

Such a light-emitting element is a self-light-emitting type light-emitting element, and when it is used as a pixel of a display, there are advantages such as high visibility and no need for a backlight. Therefore, the light-emitting element is suitable for a flat panel display element. In addition, a display using the light emitting element can be manufactured to be thin and light is also a great advantage. Also, the extremely high response speed is one of the characteristics.

Since the light-emitting layers of such a light-emitting element can be formed continuously in two dimensions, planar light emission can be obtained. This is a feature that is difficult to obtain in a point light source typified by an incandescent lamp or an LED or a line light source typified by a fluorescent lamp. Further, by selecting a material, the light emission of the organic compound can be made to be light emission not containing ultraviolet light, and thus the organic compound also has a high utility value as a surface light source applicable to illumination and the like.

As described above, displays and lighting devices using organic EL elements are applied to various electronic devices, and research and development are actively conducted in pursuit of light-emitting elements having higher efficiency and longer element life. In particular, since organic compounds are mainly used in the EL layer and have a large influence on the element characteristics of the light-emitting element, research and development of various novel organic compounds have been carried out.

In the case of a light-emitting element using an organic compound, many factors affect the element life and characteristics, and particularly, the element life and characteristics of the light-emitting element greatly differ depending on the material used for a light-emitting layer. As main materials for the light-emitting layer, there are a host material and a guest material.

Organic compounds having various skeletons have been proposed as host materials. Although the characteristics and reliability of light-emitting elements using these organic compounds have been improved, they are not sufficient to meet the high demands for various characteristics such as efficiency and durability. (for example, patent document 1).

[ Prior Art document ]

[ patent document ]

[ patent document 1] Japanese patent application laid-open No. 2011-

Disclosure of Invention

Technical problem to be solved by the invention

There are various requirements for the characteristics of light-emitting elements, and development of light-emitting elements with high reliability is particularly desired. Since the characteristics of the host material affect the reliability of the light-emitting element, the development of a host material having high reliability is actively performed. In particular, development of a host material that can be used for a blue phosphor element and has high reliability is urgent.

Accordingly, an object of one embodiment of the present invention is to provide a novel organic compound. In particular, an organic compound which can be used for a light-emitting element is provided. Another object of one embodiment of the present invention is to provide a novel electron-transporting material. Another object of one embodiment of the present invention is to provide a light-emitting element with high reliability. Another object of one embodiment of the present invention is to provide a light-emitting element with high light-emitting efficiency. Another object of one embodiment of the present invention is to provide a light-emitting element with low driving voltage.

Another object of the present invention is to provide a light-emitting element, a light-emitting device, and an electronic apparatus with high reliability. Another object of the present invention is to provide a light-emitting element, a light-emitting device, and an electronic apparatus with low power consumption.

Note that the description of these objects does not hinder the existence of other objects. It is not necessary for one embodiment of the invention to achieve all of the above objectives. The above-described objects can be clearly seen from the descriptions of the specification, the drawings, the claims, and the like, and the objects can be extracted from the descriptions of the specification, the drawings, the claims, and the like.

Means for solving the problems

One embodiment of the present invention is an organic compound represented by the following general formula (G0).

[ chemical formula 1]

In the general formula (G0), X represents oxygen or sulfur, Ar ¹Represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, R ¹To R ⁵Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, A represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaromatic hydrocarbon group having 3 to 30 carbon atoms, n represents an integer of 1 to 4, Ht ¹Represents a substituted or unsubstituted fused heteroaromatic ring containing any one or more selected from a carbazole skeleton, a dibenzofuran skeleton and a dibenzothiophene skeleton, and the number of carbon atoms of the fused heteroaromatic ring is 12 to 30.

In the above structure, it is preferable that a is an aromatic hydrocarbon group having 6 to 30 carbon atoms, the aromatic hydrocarbon group having 6 to 30 carbon atoms having at least one condensed ring. By adopting this structure, an electrochemically stable organic compound can be obtained.

Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[ chemical formula 2]

In the general formula (G1), X represents oxygen or sulfur, Ar ¹And Ar ²Each independently represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, R ¹To R ⁵Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, n represents an integer of 1 to 4, l represents an integer of 0 to 4, Ht ¹And Ht ²Each independently represents a substituted or unsubstituted fused heteroaromatic ring containing any one or more selected from a carbazole skeleton, a dibenzofuran skeleton and a dibenzothiophene skeleton, and the number of carbon atoms of the fused heteroaromatic ring is 12 to 30.

Another embodiment of the present invention is an organic compound represented by the following general formula (G2).

[ chemical formula 3]

In the general formula (G2), X represents oxygen or sulfur, Ar ¹And Ar ²Each independently represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, R ¹To R ⁵Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, n represents an integer of 1 to 4, l represents an integer of 0 to 4, Ht ¹And Ht ²Each independently represents a substituted or unsubstituted fused heteroaromatic ring containing any one or more selected from a carbazole skeleton, a dibenzofuran skeleton and a dibenzothiophene skeleton, and the number of carbon atoms of the fused heteroaromatic ring is 12 to 30.

Another embodiment of the present invention is an organic compound represented by the following general formula (G3).

[ chemical formula 4]

In the general formula (G3), X represents oxygen or sulfur, Ar ¹And Ar ²Each independently represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, R ¹To R ⁵Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, n represents an integer of 1 to 4, l represents an integer of 0 to 4, Ht ¹And Ht ²Each independently represents a substituted or unsubstituted fused heteroaromatic ring containing any one or more selected from a carbazole skeleton, a dibenzofuran skeleton and a dibenzothiophene skeleton, and the number of carbon atoms of the fused heteroaromatic ring is 12 to 30.

Another embodiment of the present invention is an organic compound represented by the following general formula (G4).

[ chemical formula 5]

In the general formula (G4), X represents oxygen or sulfur, R ¹To R ⁵Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, n represents an integer of 1 to 4, l represents an integer of 0 to 4, Ht ¹And Ht ²Each independently represents a substituted or unsubstituted fused heteroaromatic ring containing any one or more selected from a carbazole skeleton, a dibenzofuran skeleton and a dibenzothiophene skeleton, and the number of carbon atoms of the fused heteroaromatic ring is 12 to 30.

Another embodiment of the present invention is an organic compound represented by the following general formula (G5).

[ chemical formula 6]

In the above structure, it is preferable that Ht ¹And Ht ²Each independently represents any one of groups represented by the following general formulae (Ht-1) to (Ht-4). By adopting this structure, an organic compound having high electron-transporting properties and hole-transporting properties can be obtained.

[ chemical formula 7]

In the general formulae (Ht-1) to (Ht-4), R ⁹To R ¹⁴Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. Note that R ⁶To R ⁹They may be bonded to each other to form a saturated ring or an unsaturated ring.

Another embodiment of the present invention is an organic compound represented by the following general formula (G6).

[ chemical formula 8]

In the general formula (G6), X, Z ¹And Z ²Each independently represents oxygen or sulfur.

Another embodiment of the present invention is an organic compound represented by the following general formula (100).

[ chemical formula 9]

Another embodiment of the present invention is a light-emitting element including the organic compound described in any one of the above structures.

In addition, the light-emitting element having the above-described structure includes an EL layer between an anode and a cathode. Preferably, the EL layer includes at least a light-emitting layer. The EL layer may also include a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer or other functional layers.

Another embodiment of the present invention is a display device including: a light-emitting element having the above structure; and at least one of a color filter and a transistor. Another embodiment of the present invention is an electronic device including: the display device; and at least one of a housing and a touch sensor. Another aspect of the present invention is a lighting device including: a light-emitting element having the above structure; and at least one of a housing and a touch sensor. In addition, one embodiment of the present invention includes, in its scope, not only a light-emitting device including a light-emitting element but also an electronic device including a light-emitting device. Therefore, the light-emitting device in this specification refers to an image display device or a light source (including a lighting device). In addition, the following modules are also an embodiment of the present invention: a module in which a connector such as an FPC (Flexible printed circuit) or a TCP (Tape Carrier Package) is mounted in the light emitting element; a module having a printed wiring board provided in an end portion of the TCP; or a module in which an IC (integrated circuit) is directly mounted On a light-emitting element by a COG (Chip On Glass) method.

Effects of the invention

According to one embodiment of the present invention, a novel organic compound can be provided. In particular, an organic compound which can be used for a light-emitting element can be provided. In addition, according to one embodiment of the present invention, a novel electron-transporting material can be provided. In addition, according to one embodiment of the present invention, a light-emitting element with high reliability can be provided. In addition, according to one embodiment of the present invention, a light-emitting element with high light-emitting efficiency can be provided. In addition, according to one embodiment of the present invention, a light-emitting element with low driving voltage can be provided.

In addition, according to another embodiment of the present invention, a light-emitting element, a light-emitting device, and an electronic device with high reliability can be provided. In addition, according to another embodiment of the present invention, a light-emitting element, a light-emitting device, and an electronic device with low power consumption can be provided.

Note that the description of these effects does not hinder the existence of other effects. Note that one mode of the present invention is not required to achieve all the above-described effects. The effects other than the above are obvious from the descriptions of the specification, the drawings, the claims, and the like, and can be extracted from the descriptions of the specification, the drawings, the claims, and the like.