Organic electroluminescent compounds, layers and organic electroluminescent device using the same

Patent metadata

Field	Value
Publication number	US-9287512-B2
Application number	US-201514825517-A
Country	US
Kind code	B2
Filing date	Aug 13, 2015
Priority date	Mar 8, 2011
Publication date	Mar 15, 2016
Grant date	Mar 15, 2016

Abstract

The present invention relates to a novel organic electroluminescent compound, layer and an organic electroluminescent device using the same. Said organic luminescent compound provides an organic light emitting layer and/or device which has high luminous efficiency and a long operation lifetime and requires a low driving voltage improving power efficiency and power consumption.

First claim

What is claimed is:

1. A light emitting layer, comprising:
an organic electroluminescent compound as a host material in the layer; and
an iridium complex dopant,
wherein the organic electroluminescent compound is represented by the following Formula 1; and the iridium complex dopant is represented by the following Formula 2:

wherein:
L 1 represents a single bond;
X 1 represents N;
Y represents —NR 13 —;
Ar 1 represents a single bond, a substituted or unsubstituted 5- to 30-membered heteroarylene group, a substituted or unsubstituted (C6-C30)arylene group;
Ar 2 represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group;
R 1 to R 5 each independently represent hydrogen, deuterium, a halogen, as substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group fused with at least one (C3-C30)cycloalkyl group, a 5- or 7-membered heterocycloalkyl group fused with at least one substituted or unsubstituted (C6-C30)aromatic ring, (C3-C30)cycloalkyl group fused with at least one substituted or unsubstituted (C6-C30)aromatic ring, —NR 14 R 15 , —SiR 16 R 17 R 18 , —SR 19 , —OR 20 , a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a cyano group, a nitro group, or a hydroxyl group; or are linked to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene group or a substituted or unsubstituted (C3-C30)alkenylene group to form a mono- or polycyclic alicyclic ring or a mono- or polycyclic aromatic ring whose carbon atom(s) may be substituted by at least one hetero atom selected from nitrogen, oxygen and sulfur;
R 13 to R 20 have the same meaning as one of R 1 to R 5 ,
a, b and e each independently represent an integer of 1 to 4; where a, b or e is an integer of 2 or more, each of R 1 , each of R 2 or each of R 5 is the same or different;
c and d each independently represent an integer of 1 to 3; where c or d is an integer of 2 or more, each of R 3 or each of R 4 is the same or different; and
the heterocycloalkyl group and the heteroaryl(ene) group contain at least one hetero atom selected from B, N, O, S, P(═O), Si and P, and
M 1 L 101 L 102 L 103   [Formula 2]

wherein
M 1 is Ir;
L 101 and L 102 are the same and represent

 and
L 103 represents

wherein R 201 to R 203 each independently represent hydrogen, deuterium, or a (C1-C30)alkyl group;
R 206 to R 208 , R 210 , and R 212 to R 215 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group; and
R 209 and R 211 each independently represent a substituted or unsubstituted (C1-C30)alkyl group.

2. The light emitting layer of claim 1 , wherein R 209 and R 211 each independently represent unsubstituted (C1-C10)alkyl group, and wherein R 207 , R 208 , R 210 , R 214 and R 215 each independently represent hydrogen or deuterium.

3. The light emitting layer of claim 1 , wherein the iridium complex dopant is selected from:

4. The light emitting layer of claim 1 , wherein the iridium complex dopant is:

5. The light emitting layer of claim 1 , wherein R 13 is a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group, a substituted or unsubstituted (C6-C30)aryl group fused with at least one (C3-C30)cycloalkyl group, a 5- or 7-membered heterocycloalkyl group fused with at least one substituted or unsubstituted (C6-C30)aromatic ring, or a (C3-C30)cycloalkyl group fused with at least one substituted or unsubstituted (C6-C30)aromatic ring.

6. The light emitting layer of claim 2 , wherein R 13 is a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group.

7. The light emitting layer of claim 2 , wherein R 13 is substituted or unsubstituted (C6-C30)aryl group.

8. The light emitting layer of claim 1 , wherein the organic electroluminescent compound as a host material is selected from the following compounds C-1, C-5, C-9, or C-77:

9. The light emitting layer of claim 3 , wherein the organic electroluminescent compound as a host material is selected from the following compounds C-1, C-5, C-9, or C-77:

10. The light emitting layer of claim 1 , wherein the organic electroluminescent compound as a host material is selected from the following compounds C-135, C-136 or C-137:

11. The light emitting layer of claim 4 , wherein the organic electroluminescent compound as a host material is selected from the following compounds C-135, C-136 of C-137:

12. The light emitting layer of claim 3 , wherein one of (a) R 1 to R 5 each independently represent hydrogen or a substituted or unsubstituted (C6-C30)aryl group; (b) R 3 represents a substituted or unsubstituted (C6-C30)aryl group; or (c) R 4 represents a substituted or unsubstituted (C6-C30)aryl group.

13. The light emitting layer of claim 4 , wherein one of (a) R 1 to R 5 each independently represent hydrogen or a substituted or unsubstituted (C6-C30)aryl group; (b) R 3 represents a substituted or unsubstituted (C6-C30)aryl group; or (c) R 4 represents a substituted or unsubstituted (C6-C30)aryl group.

14. The light emitting layer of claim 3 , wherein a ratio of an amount by weight of the host material to the iridium complex ranges from about 100:1 to about 10:1.

15. The light emitting layer of claim 14 , wherein the layer luminesces red upon application of a driving voltage, and wherein the light emitting layer exhibits a peak intensity at a wavelength within a range of about 600 nm to about 700 nm and the host exhibits a glass transition temperature (T g ) of at least about 80° C.

16. The light emitting layer of claim 4 , wherein a ratio of an amount by weight of the host material to the iridium complex ranges from about 100:1 to about 10:1.

17. The light emitting layer of claim 16 , wherein the layer luminesces red upon application of

Assignees

• Rohm & Haas Elect Mat

Inventors

• Ahn Hee-Choon
• Cho Young-Jun
• Kwon Hyuck Joo
• Kim Bong-Ok
• Yoon Seok Keun
• Moon Doo-Hyeon
• Kim Hee Sook
• Lee Su-Hyun
• Shin Hyo-Nim
• Lee Kyung Joo
• Park Kyoung-Jin
• Kim Nam-Kyun

Classifications

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title