阅读说明：本技术 有机化合物、发光元件、发光装置、电子设备以及照明装置 (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 濑尾哲史 于 2018-11-08 设计创作，主要内容包括：提供一种新颖有机金属配合物。此外,提供一种耐热性高的新颖有机金属配合物。另外,提供一种色纯度高的新颖有机金属配合物。提供一种由下述通式(G1)表示的有机金属配合物,其中配位于Ir的嘧啶环具有至少一个具有氰基的苯基作为取代基,且具有氰基的苯基与嘧啶环的6位键合。<Image he="362" wi="700" file="DDA0002493356590000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(式中,R<Sup>1</Sup>至R<Sup>4</Sup>分别独立地表示氢、碳原子数为1至6的烷基、形成环的碳原子数为5至7的取代或未取代的环烷基、形成环的碳原子数为6至13的取代或未取代的芳基或者形成环的碳原子数为3至12的取代或未取代的杂芳基中的任意个。R<Sup>5</Sup>至R<Sup>9</Sup>分别独立地表示氢、碳原子数为1至6的烷基、形成环的碳原子数为6至13的取代或未取代的芳基、形成环的碳原子数为3至12的取代或未取代的杂芳基或氰基中的任意个,至少一个表示氰基。L表示单阴离子配体。此外,n表示1至3的整数。)。(A novel organometallic complex is provided. Further, a novel organometallic complex having high heat resistance is provided. In addition, a novel organometallic complex having high color purity is provided. An organometallic complex represented by the following general formula (G1) is provided, in which a pyrimidine ring coordinated to Ir has at least one phenyl group having a cyano group as a substituent, and the phenyl group having a cyano group is bonded to the 6-position of the pyrimidine ring. (in the formula, R 1 To R 4 Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms in a ring, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring. R 5 To R 9 Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring, or a cyano group, and at least one represents a cyano group. L represents a monoanionic ligand. Further, n represents an integer of 1 to 3. ).)

1. An organometallic complex represented by a general formula (G1).

[ chemical formula 1]

(in the general formula (G1), R¹To R⁴Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms in a ring, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring. R⁵To R⁹Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring, or a cyano group, and at least one represents a cyano group. L represents a monoanionic ligand. Further, n represents an integer of 1 to 3. )

2. An organometallic complex represented by a general formula (G1).

[ chemical formula 2]

(in the general formula (G1), R¹To R⁴Each independently represents hydrogen or a carbon atom number of 1 to 6Any of an alkyl group, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms in a ring, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring. R⁵To R⁹Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring, or a cyano group. Furthermore, R⁶To R⁸Any one of them represents a cyano group. L represents a monoanionic ligand. Further, n represents an integer of 1 to 3. )

3. The organometallic complex according to claim 1 or 2,

wherein said n is 2.

4. The organometallic complex according to any one of claims 1 to 3,

wherein the monoanionic ligand is any of a monoanionic bidentate chelate ligand having a β -diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, a monoanionic bidentate chelate ligand having a phenolic hydroxyl group, a monoanionic bidentate chelate ligand in which both ligand elements are nitrogen, and an aromatic heterocyclic bidentate ligand which forms a metal-carbon bond with iridium by cyclometallation.

5. The organometallic complex according to any one of claims 1 to 3,

wherein the monoanionic ligand is an organometallic complex of any of the following general formulae (L1) to (L8).

[ chemical formula 3]

(in the formula, R⁷¹To R⁷⁷And R⁸⁷To R¹³¹Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a cyclic carbon number of 5A substituted or unsubstituted cycloalkyl group having 1 to 6 carbon atoms, a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. Furthermore, A¹To A³Each independently represents sp bonded to nitrogen or hydrogen²Hybridized carbon or substituted sp²And a hybrid carbon, wherein the substituent represents any one of an alkyl group having 1 to 6 carbon atoms, a halogen group, a haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. )

6. The organometallic complex according to claim 1 or 2,

wherein said n is 3.

7. An organometallic complex represented by a general formula (G2).

[ chemical formula 4]

(in the general formula (G2), R¹To R⁴Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms in a ring, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring. R⁵To R⁹Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring, and a cyano group, and at least one represents a cyano group. R⁷¹And R⁷³Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted carbon atomAn alkoxy group having a number of 1 to 6, a substituted or unsubstituted alkylthio group having a carbon number of 1 to 6, or a substituted or unsubstituted aryl group having a carbon number of 6 to 13 forming a ring. )

8. An organometallic complex represented by a general formula (G2).

[ chemical formula 5]

(in the general formula (G2), R¹To R⁴Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms in a ring, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring. R⁵To R⁹Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring, or a cyano group. R⁶To R⁸Any one of them represents a cyano group. R⁷¹And R⁷³Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms in a ring, a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring. )

9. An organometallic complex represented by the following structural formula (100).

[ chemical formula 6]

10. A light-emitting element using the organometallic complex according to any one of claims 1 to 9.

11. A light-emitting device is provided with a light-emitting element,

wherein an EL layer is provided between a pair of electrodes,

and the EL layer contains the organometallic complex according to any one of claims 1 to 9.

12. A light-emitting device is provided with a light-emitting element,

wherein an EL layer is provided between a pair of electrodes,

the EL layer includes a light-emitting layer,

and, the light-emitting layer contains the organometallic complex according to any one of claims 1 to 9.

13. A light-emitting device is provided with a light-emitting element,

wherein an EL layer is provided between a pair of electrodes,

the EL layer includes a light-emitting layer,

the light-emitting layer includes a plurality of organic compounds,

and one of the plurality of organic compounds is the organometallic complex according to any one of claims 1 to 9.

14. A light emitting device comprising:

the light-emitting element according to any one of claims 10 to 13; and

a transistor or a substrate.

15. An electronic device, comprising:

the light-emitting device according to claim 14; and

microphone, camera, operating buttons, external connections or speaker.

16. An illumination device, comprising:

the light-emitting device according to claim 14; and

a housing, cover, or support.

Technical Field

One embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, an electronic device, and a lighting device. One embodiment of the present invention is not limited to this. That is, one embodiment of the present invention relates to an object, a method, a manufacturing method, or a driving method. In addition, one embodiment of the present invention relates to a process (process), a machine (machine), a product (manufacture), or a composition (machine). Specifically, a semiconductor device, a display device, a liquid crystal display device, and the like can be given as examples.

Background

Since a light-emitting element (also referred to as an organic EL element) including an EL layer between a pair of electrodes has characteristics such as thinness, lightness in weight, high-speed response to an input signal, and low power consumption, a display using the light-emitting element is expected to be used as a next-generation flat panel display.

In the light-emitting element, when a voltage is applied between a pair of electrodes, electrons and holes injected from the respective electrodes are recombined in the EL layer, and a light-emitting substance (organic compound) included in the EL layer is brought into an excited state, and light is emitted when the excited state returns to a ground state. Further, as the kind of excited state, a singlet excited state (S) may be mentioned^＊) And triplet excited state (T)^＊) In this case, light emission from a singlet excited state is referred to as fluorescence, and light emission from a triplet excited state is referred to as phosphorescence. In addition, in the light-emitting element, the statistical generation ratio of the singlet excited state and the triplet excited state is considered to be S^＊： T^＊＝1：3。

Among the above-mentioned light-emitting substances, a compound capable of converting energy in a singlet excited state into light emission is referred to as a fluorescent compound (fluorescent material), and a compound capable of converting energy in a triplet excited state into light emission is referred to as a phosphorescent compound (phosphorescent material).

Therefore, based on the above generation ratio, the theoretical limit of the internal quantum efficiency (the ratio of generated photons to injected carriers) of the light-emitting element using a fluorescent material is considered to be 25%, and the theoretical limit of the internal quantum efficiency of the light-emitting element using a phosphorescent material is considered to be 75%.

In other words, a light-emitting element using a phosphorescent material can obtain higher efficiency than a light-emitting element using a fluorescent material. Therefore, in recent years, various phosphorescent materials have been actively researched and developed. In particular, an organometallic complex having iridium or the like as a central metal has been attracting attention because of its high phosphorescence quantum yield (for example, see patent document 1).

[ Prior Art document ]

[ patent document ]

[ patent document 1] Japanese patent application laid-open No. 2009-023938

Disclosure of Invention

Technical problem to be solved by the invention

As reported in patent document 1, although the development of phosphorescent materials having excellent characteristics has been advanced, the development of novel materials having more excellent characteristics is desired.

Accordingly, one embodiment of the present invention provides a novel organometallic complex. One embodiment of the present invention provides a novel organometallic complex having high heat resistance. One embodiment of the present invention provides a novel organometallic complex that is not easily decomposed upon sublimation. One embodiment of the present invention provides a novel organometallic complex having high color purity. One embodiment of the present invention provides a novel organometallic complex having high molecular orientation. One embodiment of the present invention provides a novel organometallic complex which can be used for a light-emitting element. One embodiment of the present invention provides a novel organometallic complex which can be used for an EL layer of a light-emitting element. One embodiment of the present invention can provide a novel light-emitting element with high efficiency and high reliability using the novel organometallic complex according to one embodiment of the present invention. One embodiment of the present invention provides a novel light-emitting device, a novel electronic device, or a novel lighting device. 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. Other objects than the above can be understood and extracted from the description of the specification, drawings, claims, and the like.

Means for solving the problems

One embodiment of the present invention is an organometallic complex represented by the following general formula (G1), in which a pyrimidine ring coordinated to Ir has at least one phenyl group having a cyano group as a substituent, and the phenyl group having a cyano group is bonded to the 6-position of the pyrimidine ring.

[ chemical formula 1]

Note that, in the general formula (G1), R¹To R⁴Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms in a ring, or a C6 to C13 substituent in a ringAny of substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms forming a ring. R⁵To R⁹Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring, or a cyano group, and at least one represents a cyano group. L represents a monoanionic ligand. Further, n represents an integer of 1 to 3.

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

[ chemical formula 2]

Note that, in the general formula (G1), R¹To R⁴Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms in a ring, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring. R⁵To R⁹Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring, or a cyano group. R⁶To R⁸Any one of them represents a cyano group. L represents a monoanionic ligand. Further, n represents an integer of 1 to 3.

In the structure represented by the above general formula (G1), n is 2.

In each of the above structures, the monoanionic ligand is any of a monoanionic bidentate chelate ligand having a β -diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, a monoanionic bidentate chelate ligand having a phenolic hydroxyl group, a monoanionic bidentate chelate ligand in which both ligand elements are nitrogen, and an aromatic heterocyclic bidentate ligand which forms a metal-carbon bond with iridium by cyclometallation.

In each of the above structures, the monoanionic ligand is any of the following general formulae (L1) to (L8).

[ chemical formula 3]

Note that, in the above general formulae (L1) to (L8), R⁷¹To R⁷⁷And R⁸⁷To R¹³¹Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms in a ring, a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring. A. the¹To A³Each independently represents sp bonded to nitrogen or hydrogen²Hybridized carbon or substituted sp²And a hybrid carbon, wherein the substituent represents any of an alkyl group having 1 to 6 carbon atoms, a halogen group, a haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group.

In the structure represented by the above general formula (G1), n is 3.

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

[ chemical formula 4]

Note that, in the general formula (G2), R¹To R⁴Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms in a ring, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring. R⁵To R⁹Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a salt thereofAny of a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms or a cyano group, at least one of which represents a cyano group. R⁷¹And R⁷³Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms in a ring, a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring.

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

[ chemical formula 5]

Note that, in the general formula (G2), R¹To R⁴Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms in a ring, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring. R⁵To R⁹Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms in a ring, or a cyano group. R⁶To R⁸Any one of them represents a cyano group. R⁷¹And R⁷³Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms in a ring, a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring.

Another embodiment of the present invention is an organometallic complex in which a pyrimidine ring coordinated to Ir has at least one phenyl group having a cyano group as a substituent, and a phenyl group having a cyano group at a para-position or a meta-position is bonded to the 6-position of the pyrimidine ring.

Another embodiment of the present invention is an organometallic complex represented by structural formula (100).

[ chemical formula 6]

Another embodiment of the present invention is a light-emitting element using an organometallic complex, in which a pyrimidine ring provided with Ir has at least one phenyl group having a cyano group as a substituent, and the phenyl group having a cyano group is bonded to the 6-position of the pyrimidine ring. Note that a light-emitting element containing an organic compound other than the organometallic complex is also included in one embodiment of the present invention.

Another embodiment of the present invention is a light-emitting element using the organometallic complex according to one embodiment of the present invention. Note that one embodiment of the present invention also includes a light-emitting element in which the organometallic complex according to one embodiment of the present invention is used for an EL layer between a pair of electrodes or a light-emitting layer in the EL layer. In addition, a light-emitting device including a transistor, a substrate, or the like in addition to a light-emitting element is also included in the scope of the invention. Also, in addition to the above-described light-emitting device, an electronic apparatus and a lighting device including a microphone, a camera, an operation button, an external connection portion, a housing, a cover, a stand, a speaker, or the like are included in the scope of the invention.

The organometallic complex according to one embodiment of the present invention can be used in a light-emitting layer of a light-emitting element in combination with another organic compound. That is, light emission from the triplet excited state can be obtained from the light-emitting layer, and thus the light-emitting element can be highly efficiently provided. Thus, one embodiment of the present invention includes a light-emitting element in which a combination of the organometallic complex according to one embodiment of the present invention and another organic compound is used for a light-emitting layer. Furthermore, the light-emitting layer may also comprise a tertiary-substance.

In addition, one embodiment of the present invention includes not only a light-emitting device including a light-emitting element but also a lighting 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 light-emitting device further includes the following modules: a module that connects a connector such as FPC (Flexible printed circuit) or TCP (Tape Carrier Package) to the light emitting device; a module for arranging the printed circuit board at the end 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

One embodiment of the present invention can provide a novel organometallic complex. One embodiment of the present invention can provide a novel organometallic complex having high heat resistance. One embodiment of the present invention can provide a novel organometallic complex which is not easily decomposed upon sublimation. One embodiment of the present invention can provide a novel organometallic complex having high color purity. One embodiment of the present invention can provide a novel organometallic complex having high molecular orientation. One embodiment of the present invention can provide a novel organometallic complex which can be used for a light-emitting element. One embodiment of the present invention can provide a novel organometallic complex which can be used for an EL layer of a light-emitting element. One embodiment of the present invention can provide a novel light-emitting element with high efficiency and high reliability using the novel organometallic complex according to one embodiment of the present invention. One embodiment of the present invention can provide a novel light-emitting device, a novel electronic device, or a novel lighting device. Note that the description of these effects does not hinder the existence of other effects. One embodiment of the present invention does not necessarily have all the effects described above. Effects other than the above can be understood and extracted from the descriptions of the specification, the drawings, the claims, and the like.