IP Library Granted Patent US 9,899,600
Granted Patent B2
US 9,899,600 · App. 14/090,648 · Granted Feb 20, 2018

Multicyclic aromatic compound and organic light emitting device using the same

Inventors: Do-Hyung Lee (Yongin, KR); Dong-Jun Kim (Osan, KR); Young-Seok No (Cheongwon-gun, KR); Hyundong Chun (Seoul, KR); Joo-Dong Lee (Seongnam, KR)
Assignee: Heesung Material Ltd.
H01L51/0054C07C13/62C07C13/66C07C211/54C07D209/08C07D209/86C07D263/57C07D277/66C07F7/0818C09B1/00C09B57/00C09B57/001C09B57/008C09K11/06H01L51/0058H05B33/14C07B2200/05C07C2602/08C07C2603/18C07C2603/20C07C2603/24C07C2603/26C07C2603/28C07C2603/40C07C2603/50C07C2603/54C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1033
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Quick Facts
Patent No.
US 9,899,600
App. No.
14/090,648
Granted
Feb 20, 2018
Kind
B2
Abstract

The present specification describes a multicyclic aromatic ring compound having a novel structure and an organic light emitting device using the same.

Claims (106)

1. A compound of the following Chemical Formula 1:

wherein, in Chemical Formula 1,

R 1 and R 2 are different from each other,

R 1 and R 2 are each independently anthracenyl; phenanthrenyl; pyrenyl; triphenylenyl; phenyl-or alkyl-substituted fluorenyl; phenyl-substituted or unsubstituted carbazolyl; naphthyl, arylamine or dimethylfluorenyl-substituted or unsubstituted phenyl; biphenyl; alkyl- substituted or unsubstituted indenyl; acenaphthylenyl; fluoranthenyl; phenyl-substituted naphthyl; indolyl; benzoxazolyl; or benzothiazolyl,

at least one of R 1 or R 2 is a substituent having seven or more carbons in ring members, or a substituent including two or more rings,

R 3 to R 10 are each independently hydrogen or a monovalent organic substituent; and

R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 or R 9 and R 10 may form a monocyclic or multicyclic aliphatic ring, or a monocyclic or multicyclic aromatic ring, by being linked through C 3 -C 30 alkylene or C 3 -C 30 alkenylene that does or does not include a fused ring.

2. The compound of claim 1 , wherein R 3 to R 10 are each independently

hydrogen,

halogen,

substituted or unsubstituted C 1 -C 30 alkyl,

substituted or unsubstituted C 6 -C 30 aryl,

substituted or unsubstituted C 6 -C 30 aryl in which one or more of substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 3 -C 30 heteroaryl and substituted or unsubstituted 5-membered to 7-membered heterocycloalkyl are fused,

substituted or unsubstituted C 3 -C 30 heteroaryl,

substituted or unsubstituted C 3 -C 30 heteroaryl in which one or more of substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 6 -C 30 aromatic ring and substituted or unsubstituted 5-membered to 7-membered heterocycloalkyl are fused,

substituted or unsubstituted 5-membered to 7-membered heterocycloalkyl,

substituted or unsubstituted 5-membered to 7-membered heterocycloalkyl in which one or more of substituted or unsubstituted C 3 -C 30 heterocycloalkyl, a substituted or unsubstituted C 6 -C 30 aromatic ring and substituted or unsubstituted C 3 -C 30 heteroaryl are fused,

substituted or unsubstituted C 3 -C 30 cycloalkyl,

substituted or unsubstituted C 3 -C 30 cycloalkyl in which one or more of substituted or unsubstituted C 3 -C 30 heterocycloalkyl, a substituted or unsubstituted C 6 -C 30 aromatic ring and substituted or unsubstituted C 3 -C 30 heteroaryl are fused,

cyano,

—NR 11 R 12 ,

—SiR 13 R 14 R 15 ,

—OR 16 ,

—SR 17 ,

substituted or unsubstituted (C 6 -C 30 )ar(C 1 -C 30 )alkyl,

substituted or unsubstituted C 1 -C 30 alkylamino, C 3 -C 30 heteroaryl in which —SiR 18 R 19 R 20 is substituted,

substituted or unsubstituted C 6 -C 30 arylamino,

substituted or unsubstituted C 2 -C 30 alkenyl,

substituted or unsubstituted C 2 -C 30 alkynyl,

carboxyl,

nitro or

hydroxy,

or form a monocyclic or multicyclic aliphatic ring, or a monocyclic or multicyclic aromatic ring, by being linked to an adjacent substituent through C 3 -C 30 alkylene or C 3 -C 30 alkenylene that does or does not include a fused ring,

R 11 to R 20 are each independently hydrogen; substituted or unsubstituted C 1 -C 30 alkyl; substituted or unsubstituted C 6 -C 30 aryl; or substituted or unsubstituted C 3 -C 30 heteroaryl.

3. The compound of claim 2 , wherein, in “substituted or unsubstituted” of R 1 to R 10 , substituted means being each independently further substituted with one or more selected from the group consisting of deuterium, halogen, C 1 -C 30 alkyl in which halogen is substituted or unsubstituted, C 6 -C 30 aryl, C 3 -C 30 heteroaryl in which C 6 -C 30 aryl is substituted or unsubstituted, 5-membered to 7-membered heterocycloalkyl, 5-membered to 7-membered heterocycloalkyl in which one or more aromatic rings are fused, C 3 -C 30 cycloalkyl, C 3 -C 30 cycloalkyl in which one or more aromatic rings are fused, tri(C 1 -C 30 )alkylsilyl, di(C 1 -C 30 )alkyl(C 6 -C 30 )arylsilyl, tri(C 6 -C 30 )arylsilyl, C 2 -C 30 alkenyl, C 2 -C 30 alkynyl, cyano, carbazolyl, —NR 31 R 32 , —SiR 33 R 34 R 35 , —OR 36 , —SR 37 , (C 6 -C 30 )ar(C 1 -C 30 )alkyl, (C 1 -C 30 )alkyl(C 6 -C 30 )aryl, C 1 -C 30 alkyloxy, C 1 -C 30 alkylthio, C 6 -C 30 aryloxy, C 6 -C 30 arylthio, carboxyl, nitro or hydroxy, and R 31 to R 37 are each independently hydrogen, C 1 -C 30 alkyl, C 6 -C 30 aryl or C 3 -C 30 heteroaryl, or form a monocyclic or multicyclic aliphatic ring, or a monocyclic or multicyclic aromatic ring, by being linked to an adjacent substituent through C 3 -C 30 alkylene or C 3 -C 30 alkenylene that does or does not include a fused ring.

4. The compound of claim 1 , wherein R 3 to R 10 are each independently selected from the group consisting of

hydrogen,

halogen,

methyl,

ethyl,

propyl,

butyl,

pentyl,

hexyl,

ethylhexyl,

heptyl,

octyl,

phenyl,

naphthyl,

fluorenyl,

biphenyl,

phenanthryl,

terphenyl,

pyrenyl,

furylenyl,

spirobifluorenyl,

fluoranthenyl,

crycenyl,

triphenylenyl,

1,2-dihydroacenaphthyl,

dibenzothiophenyl,

dibenzofuryl,

carbazolyl,

pyridyl,

furyl,

thienyl,

quinolyl,

triazinyl,

pyrimidinyl,

pyridazinyl,

quinoxalinyl,

phenanthrolinyl,

benzopyrolidino,

benzopiperidino,

dibenzomorpholino,

dibenzoazepino,

amino substituted by phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, furylenyl, spirobifluorenyl, fluoranthenyl, crycenyl, triphenylenyl, dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl or phenanthrolinyl,

biphenyloxy,

biphenylthio,

biphenylmethyl,

triphenylmethyl,

carboxyl,

nitro and

hydroxy.

5. The compound of claim 1 , wherein Chemical Formula 1 is represented by any one of Chemical Formulae 2 to 9:

wherein, in Chemical Formulae 2 to 9,

R 1 , R 2 , R 3 and R 4 are the same as those defined in claim 1 ,

p and q each independently represent an integer of 1 to 4,

Y1 to Y4 represent one of substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 3 -C 30 heteroaryl, substituted or unsubstituted 5-membered to 7-membered heterocycloalkyl and substituted or unsubstituted C 6 -C 30 aryl, or a ring in which two or more of these rings are fused.

6. The compound of claim 1 selected from the group consisting of the following structural formulae:

7. An organic light emitting device comprising:

a first electrode;

a second electrode; and

one or more organic material layers provided between the first electrode and the second electrode,

wherein one or more layers of the organic material layers include the compound of Chemical Formula 1 of claim 1 .

8. The organic light emitting device of claim 7 , wherein the one or more organic material layers that includes the compound of Chemical Formula 1 is a light emitting layer.

9. The organic light emitting device of claim 7 , wherein the one or more organic material layers that includes the compound of Chemical Formula 1 further includes a fluorescent dopant.

10. The organic light emitting device of claim 7 , wherein the one or more organic material layers that includes the compound of Chemical Formula 1 further includes a blue fluorescent dopant.

11. The organic light emitting device of claim 7 , wherein the one or more organic material layers that includes the compound of Chemical Formula 1 further includes a phosphorescent dopant.

12. The organic light emitting device of claim 7 , wherein the one or more organic material layers that includes the compound of Chemical Formula 1 further includes one or more compounds selected from the group consisting of arylamine-based compounds or styrylarylamine-based compounds.

13. The organic light emitting device of claim 7 , wherein the one or more organic material layers that includes the compound of Chemical Formula 1 further includes one or more metals or complex compounds selected from the group consisting of group 1, group 2, period 4 and period 5 transition metals, lanthanide-series metals, and organic metals of d-transition atoms.

14. The organic light emitting device of claim 7 , further comprising:

one or more organic materials emitting blue, red or green light, in addition to the compound of Chemical Formula 1.

15. The organic light emitting device of claim 7 , further comprising:

one or more organic material layers emitting blue, red or green light, in addition to the organic material layer including the compound of Chemical Formula 1.

16. The organic light emitting device of claim 7 , which emits white light.

Assignments (2)
CHANGE OF NAME Recorded Feb 13, 2020
From: HEESUNG MATERIAL LTD.
To: LT MATERIALS CO., LTD.
Reel/Frame 051926/0419 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 27, 2013
From: LEE, DO-HYUNG; KIM, DONG-JUN; NO, YOUNG-SEOK; CHUN, HYUNDONG; LEE, JOO-DONG
To: HEESUNG MATERIAL LTD.
Reel/Frame 031688/0172 →
Priority Claims (1)
KR 10-2012-0134761 · Nov 26, 2012 · national
Continuity (1)
Related Publication 20140145169A1 · May 29, 2014