Sulfone group-containing compound, an organic light emitting diode (OLED) device having the same, and a method of fabricating the OLED device

• US 9,397,301 B2
• Filed: 06/25/2013
• Issued: 07/19/2016
• Est. Priority Date: 05/06/2013
• Status: Active Grant

• Current Assignee: Shenzhen China Star Optoelectronics Technology Co., Ltd. (TCL Technology Group Corp.)
• Original Assignee: Shenzhen China Star Optoelectronics Technology Co., Ltd. (TCL Technology Group Corp.)
• Inventors: Zou, Qinghua
• Primary Examiner(s): GARRETT, DAWN L
• Application Number:
  US13/985,938
• Publication Number:
  US 20150357584A1
• Time in Patent Office: 1,120 Days
• US Class Current: 1/1
• CPC Class Codes: C07D 333/76 Dibenzothiophenes
• CPC Class Codes: C07D 409/14 containing three or more hetero rings
• CPC Class Codes: C07F 7/0812 comprising a heterocyclic ring
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 71/00 Manufacture or treatment specially adapted for the organic devices covered by this subclass
• CPC Class Codes: H10K 71/164 using vacuum deposition
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

The present invention provides a sulfone group-containing compound, an organic light emitting diode (OLED) device using the sulfone group-containing compound, and a method of fabricating the OLED device. The sulfone group-containing compound has formula as

wherein the bridging unit R is capable of connecting to three or more than three fluorene sulfur oxide units; and the unit R₁, R₂ and R₃ respectively connected to the fluorene sulfur oxide units are selected from alkyl chains, aromatic groups or heterocyclic groups. According to the present invention, the sulfone group-containing compound connects to three or more than three fluorene sulfur oxide units with a bridging unit to form a novel star-shaped molecular structure. The sulfone groups-containing compound combines electron affinity and transport properties of the fluorene sulfur oxide units and spatial characteristics of the star-shaped molecular structure, so that efficiency and lifetime of an OLED device using the same can be enhanced.

Claims

1. A sulfone group-containing compound having three or four fluorene sulfur oxide groups, wherein a formula of the sulfone group-containing compound having three fluorene sulfur oxide groups is as:

2. The sulfone group-containing compound according to claim 1, wherein the alkyl chains are selected from a branched alkyl chain or straight alkyl chains.

3. The sulfone group-containing compound according to claim 2, wherein the branched alkyl chain is

4. The sulfone group-containing compound according to claim 1, wherein the aromatic groups are selected from

5. The sulfone group-containing compound according to claim 1, wherein the heterocyclic groups are selected from

6. An organic light emitting diode (OLED) device having a sulfone group-containing compound, comprising:

a transparent substrate;

an anode, disposed above the transparent substrate;

a hole transport layer, disposed above the anode;

a light emitting layer, disposed above the hole transport layer;

an electron transport layer, disposed above the light emitting layer; and

a cathode, disposed above the electron transport layer, wherein at least the electron transport layer or the light emitting layer comprises a sulfone group-containing compound having three or four fluorene sulfur oxide groups, wherein a formula of the sulfone group-containing compound having three fluorene sulfur oxide groups is as

7. The OLED device according to claim 6, when the light emitting layer comprises the sulfone group-containing compound, the sulfone group-containing compound is used as single host material of the light emitting layer or a component of host materials of the light emitting layer, whereas the sulfone group-containing compound is used as the component of host materials of the light emitting layer, a weight ratio of the sulfone group-containing compound to the light emitting layer is 1%˜

99%;

when the electron transport layer comprises the sulfone group-containing compound, the sulfone group-containing compound is used as single material of the electron transport layer or a component of materials of the electron transport layer, whereas the sulfone group-containing compound is used as the component of materials of the electron transport layer, a weight ratio of the sulfone group-containing compound to the electron transport layer is 1%˜

99%.

8. A method of fabricating the OLED device according to claim 6, comprising steps as follows:

Step 1, providing a transparent substrate;

Step 2, forming an anode above the transparent substrate;

Step 3, forming one or more than one hole transport layer;

Step 4, forming one or more than one light emitting layer above the hole transport layer;

Step 5, forming one or more than one electron transport layer above the light emitting layer; and

Step 6, forming a cathode above the electron transport layer, wherein at least one of the light emitting layer or the electron transport layer comprises the sulfone group-containing compound according to claim 7.

9. The method of fabricating the OLED device according to claim 8, wherein Step 4 comprises forming the sulfone group-containing compound above the hole transport layer with a vacuum evaporation deposition, the sulfone group-containing compound is used as single host material of the light emitting layer or a component of host materials of the light emitting layer, whereas the sulfone group-containing compound is used as the component of host materials of the light emitting layer, a weight ratio of the sulfone group-containing compound to the light emitting layer is 1%˜

99%.

10. The method of fabricating the OLED device according to claim 8, wherein Step 5 comprises forming the sulfone group-containing compound above the light emitting layer with a vacuum evaporation deposition, and the sulfone group-containing compound is used as single material of the electron transport layer or a component of materials of the electron transport layer, whereas the sulfone group-containing compound is used as the component of materials of the electron transport layer, a weight ratio of the sulfone group-containing compound to the electron transport layer is 1%˜

99%.