Fluoro group-containing compound, fluoro group-containing polymer, organic light emitting device including the polymer, and method of manufacturing the device

Patent metadata

Field	Value
Publication number	US-9419224-B2
Application number	US-82383210-A
Country	US
Kind code	B2
Filing date	Jun 25, 2010
Priority date	Nov 20, 2009
Publication date	Aug 16, 2016
Grant date	Aug 16, 2016

Abstract

A fluoro group-containing compound, a fluoro group-containing polymer, an organic light emitting device including the polymer, and a method of manufacturing the organic light emitting device are provided.

First claim

What is claimed is:

1. A fluoro group-containing polymer represented by Formula 11 below:

wherein T 1 is a substituted or unsubstituted C 6 -C 30 aromatic ring;
T 2 is a bivalent linking group represented by —[C(R 1 )(R 2 )] q —, wherein R 1 and R 2 are a hydrogen atom, q is 10, and i) one of —C(R 1 )(R 2 )— is replaced —O— or a substituted or unsubstituted C 6 -C 30 arylene group; two of —C(R 1 )(R 2 )— are each independently replaced —O— or a substituted or unsubstituted C 6 -C 30 arylene group; or iii) three of —C(R 1 )(R 2 )— are each independently replaced —O— or a substituted or unsubstituted C 6 -C 30 arylene group;
T 3 is represented by —(R 3 ) r —R 4 , wherein R 3 is selected from a fluoro group-containing C 6 -C 30 arylene group, R 4 is selected from a halogen atom, and r is 1, wherein the R 3 s may be same or different from each other;
p is 2;
Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted C 3 -C 30 heteroarylene group;
a, b, and c are each independently a real number satisfying 0<a≦0.99, 0<b≦0.99, and c−0, and a+b+c−1; and
each “*” indicates a point of attachment to the same or a different polymeric unit represented by Formula 11.

2. The fluoro group-containing polymer of claim 1 , wherein T 1 is an anthracene ring, a fluorene ring, a pyrene ring, or a chrysene ring.

3. The fluoro group-containing polymer of claim 1 , wherein T 2 is represented by Formula 2A or 2B below:

wherein * is a binding site to T 1 of Formula 1, *′ is a binding site to T 3 of Formula 1, and n in Formula 2A is 9 and n in Formula 2B is 7.

4. The fluoro group-containing polymer of claim 1 , wherein R 3 is a fluoro group-containing phenylene group, a fluoro group-containing naphthylene group, or a fluoro group-containing anthrylene group.

5. The fluoro group-containing polymer or claim 1 , wherein the fluorination degree of T 3 ranges from 50% to 100%.

6. The fluoro group-containing polymer of claim 1 , wherein Ar 1 and Ar 2 are each independently substituted or unsubstituted pyrrolylene, substituted or unsubstituted imidazolylene, substituted or unsubstituted pyrazolylene, substituted or unsubstituted pyridinylene, substituted or unsubstituted pyrazinylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted pyridazinylene, substituted or unsubstituted isoindolylene, substituted or unsubstituted indolylene, substituted or unsubstituted indazolylene, substituted or unsubstituted purinylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted benzoquinolinylene, substituted or unsubstituted phthalazinylene, substituted or unsubstituted naphthyridinylene, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted cinnolinylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted phenanthridinylene, substituted or unsubstituted acridinylene, substituted or unsubstituted phenanthrolinylene, substituted or unsubstituted phenazinylene, substituted or unsubstituted benzothiazolylene, substituted or unsubstituted benzooxazolylene, substituted or unsubstituted benzoimidazolylene, substituted or unsubstituted puranylene, substituted or unsubstituted benzopuranylene, substituted or unsubstituted thiophenylene, substituted or unsubstituted benzothiophenylene, substituted or unsubstituted thiazolylene, substituted or unsubstituted isothiazolylene, substituted or unsubstituted isoxazolylene, substituted or unsubstituted oxazolylene, substituted or unsubstituted benzo-oxazolylene, or any one of groups represented by Formulae 12A to 12E and 12G:

wherein X 1 to X 5 are each independently selected from O, S, C(—O), N(R 25 ), and C(R 25 )(R 26 ); R 21 , R 22 , R 25 and R 26 are each independently a hydrogen atom, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, or a substituted or unsubstituted aryl group; and
x and y are each independently an integer ranging from 1 to 4;
wherein
at least one of X 1 and X 2 in Formula 12A is O, S or N(R 25 ),
at least one of X 1 to X 3 in Formula 12B is O, S or N(R 25 ),
at least one of X 1 to X 5 in Formula 12C is O, S or N(R 25 ),
at least one of X 1 and X 4 in Formula 12 is O, S or N(R 25 )
X 1 in Formula 12E is O, S or N(R 25 ), and
each “*” indicates a point of attachment to T 1 , Ar 1 or Ar 2 in Formula 11.

7. The fluoro group-containing polymer of claim 1 , wherein Ar 1 and Ar 2 are each independently any one of groups represented by Formulae 13A through 13K and 13M below

wherein R 21 , R 22 , and R 25 are each independently a hydrogen atom; a C 1 -C 10 alkyl group; a C 1 -C 10 alkoxy group; a C 6 -C 14 aryl group; or a C 6 -C 14 aryl group substituted with at least one C 1 -C 30 alkyl group, C 1 -C 30 alkoxy group, C 2 -C 30 alkenyl group, or C 6 -C 30 aryl group; x is an integer ranging from 1 to 4; R 11 is a C 1 -C 10 alkyl group or a C 6 -C 14 aryl group; and each “*” indicates a point of attachment to T 1 , Ar 1 or Ar 2 in Formula 11.

8. The fluoro group-containing polymer of claim 1 , wherein Ar 1 is represented by Formula 14A below:

wherein R 31 to R 35 are each independently a hydrogen atom, a C 1 -C 30 alkyl group, a C 1 -C 30 alkoxy group, a C 2 -C 30 alkenyl group, or a C 6 -C 30 aryl group and each “*” indicates a point of attachment to T 1 or Ar 2 in Formula 11.

9. A fluoro group-containing polymer of claim 1 , wherein the polymer is represented by Formula 11A below:

wherein in Formula 11A,
T 2 is represented by Formula 2A or 2B;
R 31 to R 35 are each independently a hydrogen atom, a C 1 -C 30 alkyl group, a C 1 -C 30 alkoxy group, a C 2 -C 30 alkenyl group, or a C 6 -C 30 aryl group;
a and b are each independently a real number satisfying 0<a≦0.99 and 0<b≦0.99, and a+b−1; and
each “*” indicates a point of attachment to the same or a different polymeric unit represented by Formula 11A:

wherein * in Formulae 2A and 2B is a binding site to a fluorene of Formula 11A, *′ in Formulae 2A and 2B is a binding site to Formula 3A in Formula 11A and * in Formula 3A is a binding site to T 2 of Formula 11A and n in Formula 2A is 9 and n in Formula 2B is 7.

10. An organic light emitting device comprising:
a substrate; a first electrode; a second electrode; an intermediate layer that is interposed between the first electrode and the second electrode and comprising a fluoro group-containing polymer according to claim 1 ; and an emission layer (EML) that is formed close to the intermediate layer.

Assignees

• Son Jhun-Mo
• Joo Won-Jae
• Kang Ho-Suk
• Yang Hye-Yeon
• Samsung Electronics Co Ltd

Inventors

• Son Jhun-Mo
• Joo Won-Jae
• Kang Ho-Suk
• Yang Hye-Yeon

Classifications

• C08G2261/146

  Side-chains containing halogens · CPC title

• C07C43/225 Primary

  containing halogen · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C08G2261/3245

  containing nitrogen and oxygen as heteroatoms · CPC title

• H01L51/0039 Primary

  Electricity · mapped topic