Organic compound, organic light-emitting element, display device, photoelectric conversion device, electronic device, illumination device, and exposure light source

A technology of organic light-emitting elements and organic compounds, which is applied in the field of exposure light sources and can solve problems such as luminous efficiency problems

Pending Publication Date: 2022-06-28
CANON KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] When Compound 1-a disclosed in US Patent Application Publication No. 2012 / 0001537 or Compound 2-a disclosed in Chinese Patent Application Publication No. 108383847 is used for the light-emitting layer in an organic light-emitting element, there is still a problem of luminous efficiency

Method used

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  • Organic compound, organic light-emitting element, display device, photoelectric conversion device, electronic device, illumination device, and exposure light source
  • Organic compound, organic light-emitting element, display device, photoelectric conversion device, electronic device, illumination device, and exposure light source
  • Organic compound, organic light-emitting element, display device, photoelectric conversion device, electronic device, illumination device, and exposure light source

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0243] Example 1 (Synthesis of Exemplary Compound A1)

[0244] Exemplary compound A1 was synthesized according to the following scheme. The following scheme is the above reaction scheme in which the compound E1 in which X is an oxygen atom is used as the compound (a).

[0245]

[0246] (1) Synthesis of compound E3

[0247] Place the following reagents and solvents in a 300ml recovery bottle.

[0248] Compound E1: 5.0 g (27.3 mmol)

[0249] Compound E2: 7.7 g (27.3 mmol)

[0250] Pd 2 (dba) 3 : 0.7g (0.8mmol)

[0251] P(t-Bu) 3 : 0.6g (2.7mmol)

[0252] NaO-t-Bu: 5.2 g (54.6 mmol)

[0253] Toluene: 100ml

[0254] Next, the reaction solution was stirred with heating at 100° C. for 12 hours under nitrogen flow. After heating and stirring, the resultant was extracted with toluene, and the organic layer was concentrated and dried to obtain a solid. The obtained solid was purified by silica gel column chromatography (mixture of toluene and heptane) to obtain 6.5 g of ...

Embodiment 23

[0278] In this example, an organic EL element having a bottom emission structure in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode are produced was produced are sequentially formed on the substrate.

[0279] First, an ITO film is formed on a glass substrate and desirably patterned, thereby forming an ITO electrode (anode). At this time, an ITO electrode was formed so as to have a thickness of 100 nm. The substrate on which the ITO electrode was formed in this manner was used as an ITO substrate in the following steps. Next, organic compound layers and electrode layers shown in Table 5 below were successively formed on the ITO substrate by performing vacuum deposition by means of resistance heating in a vacuum chamber. At this time, the electrode area of ​​the electrode (metal electrode layer, cathode) facing the I...

Embodiment 24～27

[0283] Examples 24 to 27, Reference Example 28, and Comparative Examples 1 and 2

[0284] An organic light-emitting element was produced in the same manner as in Example 23, except that the materials for forming each layer were appropriately changed to the compounds shown in Table 6. For layers not listed in Table 6, the same composition as in Example 23 was used. The properties of the resulting element were measured and evaluated in the same manner as in Example 23. The measurement results are shown in Table 6 together with the measurement results of Example 23.

[0285] Table 6

[0286]

[0287] As shown in Table 6, in Examples 23 to 27, organic light-emitting elements each having a high maximum external quantum efficiency (E.Q.E.) and a long 5% degradation lifetime (LT95) were obtained. That is, in Examples 23 to 27, organic light-emitting elements having high luminous efficiency and high driving durability were obtained. In other words, the example compounds shown i...

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Abstract

The invention relates to an organic compound, an organic light-emitting element, a display device, a photoelectric conversion device, an electronic device, a lighting device, and an exposure light source. An organic compound represented by general formula [1-1]: In general formula [1-1], X represents an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom; r1 to R18 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted silyl group, and a cyano group.

Description

technical field [0001] The present invention relates to organic compounds, organic light-emitting elements, display devices, photoelectric conversion devices, electronic devices, lighting devices, moving bodies, and exposure light sources. Background technique [0002] An organic light-emitting element (hereinafter also referred to as "organic electroluminescent element" or "organic EL element") is an electronic element including a pair of electrodes and an organic compound layer disposed between the pair of electrodes. By injecting electrons and holes through the pair of electrodes, excitons of the light-emitting organic compound in the organic compound layer are generated. When the excitons return to their ground states, the organic light-emitting element emits light. [0003] Recent advances in organic light-emitting elements have attracted attention. For example, low driving voltage, various emission wavelengths, high-speed responsiveness, and thinning and weight reduc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/10C07D513/10C07D517/10C07D471/10C09K11/06H01L51/54G03F7/20
CPCC07D498/10C07D513/10C07D517/10C07D471/10C09K11/06G03F7/70008C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/104C09K2211/1011C09K2211/1044H10K85/636H10K85/615H10K85/631H10K85/654H10K85/6572H10K85/657C07D265/38H10K50/121H10K50/11C07D498/06C07D513/06C07D517/06H05B33/14G03G15/04045H10K59/38H10K59/12H10K50/12C09K2211/1018H10K2101/10
Inventor 西出洋祐镰谷淳山田直树岩胁洋伸宫下广和
Owner CANON KK
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