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Electronic device comprising an organic semiconducting material

a semiconducting material and electronic device technology, applied in semiconductor devices, solid-state devices, other domestic articles, etc., can solve the problems of reduced contact resistance, difficult injection of etl with very high lumo, etc., to achieve good lumo position of organic light-emitting devices, good conductivity and charge carrier mobility, and high thermal stability

Active Publication Date: 2020-08-11
NOVALED GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The materials provide high thermal stability, good dopability, conductivity, and charge carrier mobility, along with high transparency and ease of synthesis, making them suitable for organic electronic devices such as OLEDs and field-effect transistors, with a glass transition temperature of over 100°C and reduced operating voltage.

Problems solved by technology

In the case of light-emitting diodes, the ohmic losses in the charge transport layers during operation are associated with their conductivity.
Furthermore, depending on the charge carrier concentration in the organic layers, a bending of the band in the vicinity of a metal contact results which simplifies the injection of charge carriers and can therefore reduce the contact resistance.
Additionally, analogous to the experience with inorganic semiconductors, applications can be anticipated which are precisely based on the use of p- and n-doped layers in a component and otherwise would be not conceivable.
There is a technical challenge to provide electron transport materials (ETM) and emitter host (EMH) materials that have a sufficiently low laying LUMO level so that they can be doped, and still have a high enough laying LUMO level which can efficiently transfer charge to emitter host (in case of an ETM) and transfer energy to the emitter dopant (in case of EMH).
The limitation for high laying LUMO level of the ETL is given by the dopability, since the n-dopants with very high HOMO tend to be unstable; also the injection is difficult for very high LUMO of the ETL.

Method used

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  • Electronic device comprising an organic semiconducting material
  • Electronic device comprising an organic semiconducting material
  • Electronic device comprising an organic semiconducting material

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of

[0064]

[0065]First Step:

[0066]Synthesis of 2-benzylidene-3,4-dihydronaphthalen-1(2H)-one (1). All manipulations were carried out in air, without any further purification of commercial solvents / chemicals.

[0067]

[0068]A 250 mL flask was charged with tetralone (4 g, 27.4 mmol) and benzaldehyde (3.88 g, 36.6 mmol). This was dissolved in warm tetrahydrofuran (15 mL), and to this yellow solution was slowly added a 4 wt % solution of KOH in methanol (125 mL). The reaction was stirred for 4 days at room temperature. The solvent was then removed under reduced pressure, and it was poured into 150 mL of water and extracted with methylene chloride. The organic extract was dried over magnesium sulfate and filtered, and the solvent was removed at reduced pressure to afford 4.1 g (64%) as white powder.

[0069]NMR: 1H NMR (500 MHz, CD2Cl2) δ 8.01 (dd, J=64.7, 65.4, 2H), 7.71-6.92 (m, 8H), 3.39-2.64 (m, 4H).

[0070]Second Step:

[0071]Synthesis of 7-phenyl-5,6,8,9-tetrahydrodibenzo[c,h]acridine ...

example 2

Synthesis of

[0079]

[0080]First Step:

[0081]Synthesis of (E)-2-(4-bromobenzylidene)-3,4-dihydronaphthalen-1(2H)-one (4). All manipulations were carried out in air, without any further purification of commercial solvents / chemicals.

[0082]

[0083]A 250 mL flask was charged with tetralone (3.22 g, 22 mmol) and 4-bromobenzaldehyde (5.3 g, 28.6 mmol). This was dissolved in warm tetrahydrofuran (12 mL), and to this yellow solution was slowly added a 4 wt % solution of KOH in methanol (100 mL). The reaction was stirred for 4 days at room temperature. The mixture was concentrated and reduced to approx 10% vol. The residue was filtered and washed with MTBE (3*50 mL), dried, to afford a light yellow powder (6.61 g, 96%).

[0084]Second Step:

[0085]Synthesis of 7-(4-bromophenyl)-5,6,8,9-tetrahydrodibenzo[c,h]acridine (5). All manipulations were carried out under argon.

[0086]

[0087]4 (6.54 g, 20.9 mmol) and tetralone (2.93 g, 20.0 mmol) are introduced in a flask together with BF3.Et2O (3 mL, 23.7 mmol). T...

example 3

Synthesis of

[0099]

[0100]First Step:

[0101]Synthesis of (E)-2-(3-bromobenzylidene)-3,4-dihydronaphthalen-1(2H)-one (8). All manipulations were carried out in air, without any further purification of commercial solvents / chemicals.

[0102]

[0103]A 250 mL flask was charged with tetralone (5.2 g, 35.6 mmol) and 3-bromobenzaldehyde (8.51 g, 56 mmol). This was dissolved in warm tetrahydrofuran (20 mL), and to this yellow solution was slowly added a 4 wt % solution of KOH in methanol (160 mL). The reaction was stirred for 4 days at room temperature. The mixture was concentrated and reduced to approx 10% vol. The residue was filtered and washed with MTBE (3*50 mL), dried, to afford a light yellow powder (10.3 g, 92%).

[0104]NMR: 1H NMR (500 MHz, CD2Cl2) δ 8.01 (dd, J=64.7, 65.4, 2H), 7.71-6.92 (m, 8H), 3.39-2.64 (m, 4H).

[0105]Second Step:

[0106]Synthesis of 7-(3-bromophenyl)-5,6,8,9-tetrahydrodibenzo[c,h]acridine (9). All manipulations were carried out under argon.

[0107]

[0108]4 (10.2 g, 32.6 mmol)...

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Abstract

The present invention relates to an electronic device comprising at least one organic semiconducting material according to the following formula (I): wherein R1-4 are independently selected from H, halogen, CN, substituted or unsubstituted C1-C20-alkyl or heteroalkyl, C6-C20-aryl or C5-C20-heteroaryl, C1-C20-alkoxy or C6-C20-aryloxy, Ar is selected from substituted or unsubstituted C6-C20-aryl or C5-C20-heteroaryl, and R5 is selected from substituted or unsubstituted C6-C20-aryl or C5-C20-heteroaryl, H, F or formula (II).

Description

[0001]The present invention relates to an organic semiconducting layer, preferably an electronic device, comprising at least one organic semiconducting material.FIELD OF THE INVENTION[0002]Conjugated organic compounds have different applications. One important field comprises organic semiconductors. Organic semiconductors can be used to fabricate simple electronic components e.g. resistors, diodes, field effect transistors, and also optoelectronic components like organic light emitting devices (e.g. OLED), and many others. The industrial and economical significance of the organic semiconductors and their devices is reflected in the increased number of devices using organic semiconducting active layers and the increasing industry focus on the subject.[0003]A simple OLED is demonstrated in U.S. Pat. No. 4,356,429A. There, between conductive electrodes, two semiconductive organic layers are brought together: one transporting holes and the other one transporting electrons. The recombina...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): H01L51/00H01L51/50H10K99/00
CPCH01L51/0072H01L51/5028H01L51/0054H01L51/0069Y10S428/917H01L51/5052H01L51/5048H10K85/6572H10K50/14H10K50/155H10K50/165H10K71/30H10K85/622H10K85/656H10K50/11H10K50/121
Inventor FADHEL, OMRANEPRETSCH, RAMONA
Owner NOVALED GMBH
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