Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9711730-B2
Application number	US-201514985837-A
Country	US
Kind code	B2
Filing date	Dec 31, 2015
Priority date	Jan 25, 2015
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

This invention discloses novel light-emitting materials. These materials comprise a side chain which contains at least two Si or Ge atoms, such as bis(trimethylsilyl)methyl, or a side chain that includes Si—F bond, or a side chain that includes a fluorine-containing alkyl chain. This new side chain could fine tune emission color, reduce the stacking of the light-emitting materials, maintain good lifetime, and result in high PLQY.

First claim

We claim:

1. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a first compound;
wherein the first compound is capable of functioning as a fluorescent emitter in an organic light emitting device at room temperature;
wherein the first compound has at least one aromatic ring comprising at least one substituent R;
wherein each of the at least one R is an organic group selected from the group consisting of (a) a group having at least two atoms of X, (b) a group having at least one X—F bond, and (c) partially fluorinated alkyl, partially fluorinated cycloalkyl, or combinations thereof;
wherein each X is independently selected from the group consisting of Si and Ge;
wherein each of the at least one R is directly bonded to one of the aromatic rings; and
wherein in each of the at least one R, the C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.

2. The OLED of claim 1 , wherein X is directly bonded to the aromatic ring.

3. The OLED of claim 1 , wherein X is separated by at least one carbon atom from the aromatic ring.

4. The OLED of claim 1 , wherein X connects to its adjacent atoms by X—C or X—F bond only.

5. The OLED of claim 1 , wherein when each of the at least one R is (b) or (c), the first compound does not have any F atoms other than in the at least one R.

6. The OLED of claim 1 , wherein when each of the at least one R is (c), each of the at least one R contains at least one CF 3 group.

7. The OLED of claim 1 , wherein when each of the at least one R is (c), none of the at least one R contain any CF 3 groups.

8. The OLED of claim 1 , wherein each of the at least one R is independently selected from the group consisting of partially or fully silylated alkyl, partially or fully silylated cycloalkyl, partially or fully germanylated alkyl, partially or fully germanylated cycloalkyl, and combinations thereof.

9. The OLED of claim 1 , wherein each of the at least one R is selected from the group consisting of:

wherein R u , R v , R w , R x , R y , and R z are each independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, and combinations thereof.

10. The OLED of claim 1 , wherein each of the at least one R is independently selected from the group consisting of:

11. The OLED of claim 1 , wherein each of the at least one R is independently selected from the group consisting of:

12. The OLED of claim 1 , wherein each of the at least one R is independently selected from the group consisting of:

13. The OLED of claim 1 , wherein the first compound comprises at least one organic group selected from the group consisting of:

and aza analogues thereof;
wherein A is selected from the group consisting of O, S, Se, NR′ and CR′R″;
wherein R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein two adjacent substituents of R′ and R″ are optionally joined to form a ring.

14. The OLED of claim 1 , wherein the first compound is selected from the group consisting of:

wherein R 1 to R 5 each independently represent from one to the maximum number of substitutions available, or no substitution;
wherein R 1 to R 5 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and
wherein at least one of R 1 -R 5 is R.

15. The OLED of claim 1 , wherein the first compound is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Xia Chuanjun
• Lin Chun

Classifications

• C07D491/052

  the oxygen-containing ring being six-membered · CPC title

• H01L51/006

  Electricity · mapped topic

• H05B33/14 Primary

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• H01L51/0071

  Electricity · mapped topic