IP Library › Granted Patent US 10,256,412
Granted Patent B2
US 10,256,412 · App. 14/251,754 · Granted Apr 9, 2019

Anthracene-based compound and organic light-emitting device including the same

Inventors: Young-Kook Kim (Yongin, KR); Seok-Hwan Hwang (Yongin, KR); Hye-Jin Jung (Yongin, KR); Jun-Ha Park (Yongin, KR); Jong-Woo Kim (Yongin, KR); Eun-Young Lee (Yongin, KR); Jin-O Lim (Yongin, KR); Sang-Hyun Han (Yongin, KR); Eun-Jae Jeong (Yongin, KR); Kwang-Hyun Kim (Yongin, KR); Soo-Yon Kim (Yongin, KR)
Assignee: SAMSUNG DISPLAY CO., LTD.
H01L51/0058H01L51/0052H01L51/0054H01L51/0081H01L51/5016
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Quick Facts
Patent No.
US 10,256,412
App. No.
14/251,754
Granted
Apr 9, 2019
Kind
B2
Abstract

An anthracene-based compound and an organic light-emitting device including the anthracene-based compound, the anthracene-based compound being represented by Formula 1, below:

Claims (60)

1. An organic light-emitting device, comprising:

a first electrode;

a second electrode opposite to the first electrode; and

an organic layer between the first electrode and the second electrode, the organic layer including an emission layer, a hole-transporting region and an electron-transporting region,

wherein the emission layer includes an anthracene-based compound represented by Formula 1, below, as a host:

in Formula 1 above,

L is a phenylene group, an anthracenylene group, a pyrenylene group, or a fluorenylene group; or

a phenylene group, an anthracenylene group, a pyrenylene group, or a fluorenylene group, each substituted with hydrogen, deuterium, halogen, a hydroxyl group, a cyano group, a nitro group, an amino group, a carboxylic acid group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, or a substituted or unsubstituted C2-C30 heteroaryl group;

n is an integer of 0 to 3;

m is 2 or 3;

one of *-(L) n -Ar being position at carbon number 10 of the anthracene moiety of Formula 1,

R 1 and R 2 are each independently hydrogen, deuterium, halogen, a hydroxyl group, a cyano group, a nitro group, an amino group, a carboxylic acid group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, or a substituted or unsubstituted C 2 -C 30 heteroaryl group;

a1 and a2 are each independently an integer of 0 to 2; and

Ar group is independently selected from Formula 4-1 and 4-4 to 4-27, below:

in Formula 4-1 and 4-4 to 4-27 above,

Y 11 and Y 13 to Y 67 are each independently:

deuterium, a halogen atom, a cyano group, a nitro group, a methyl group, an ethyl group, a tert-butyl group, or —Si(Q 1 )(Q 2 )(Q 3 ), in which Q 1 to Q 3 are each independently a methyl group or a phenyl group, or

a phenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, or a cyclopentaphenanthrenyl group, each substituted with a methyl group;

b1 and b3 to b57 are each independently an integer of 0 to 2;

X 11 to X 38 are each independently a methyl group or a phenyl group; and

* is a binding site to an anthracene core or L.

2. The organic light emitting device as claimed in claim 1 , wherein L is:

a phenylene group, an anthracenylene group, a pyrenylene group, or a fluorenylene group; or

a phenylene group, an anthracenylene group, a pyrenylene group, or a fluorenylene group, each substituted with deuterium, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, or a tert-butyl group.

3. The organic light emitting device as claimed in claim 1 , wherein n is an integer of 0 to 2.

4. The organic light emitting device as claimed in claim 1 , wherein:

n is an integer of 1 to 3, and

a moiety represented by (L) n is represented by one of Formula 2-1, 2-2, 2-5, 2-8 and 2-9, below:

in Formulae 2-1, 2-2, 2-5, 2-8 and 2-9 above,

Z 11 to Z 26 are each independently deuterium, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, or a tert-butyl group;

c1 to c14 are each independently an integer of 0 to 3;

** is a binding site to an anthracene core, and * is a binding site to Ar.

5. The organic light emitting device as claimed in claim 1 , wherein:

n is an integer of 1 to 3, and

a moiety represented by (L) n is represented by one of Formula 3-1, 3-2, 3-5, 3-8 and 3-9, below:

in Formula 3-1, 3-2, 3-5, 3-8 and 3-9 above, ** is a binding site to an anthracene core, and * is a binding site to Ar.

6. The organic light emitting device as claimed in claim 1 , wherein the anthracene-based compound represented by Formula 1 is represented by Formula 1a below:

wherein, in Formula 1a above,

L 1 and L 2 are each independently defined the same as L of Formula 1;

n1 and n2 are each independently an integer of 0 to 2; and

Ar 1 and Ar 2 are each independently defined the same as Ar of Formula 1.

7. The organic light emitting device as claimed in claim 6 , wherein L 1 and L 2 are each independently:

a phenylene group, an anthracenylene group, a pyrenylene group, or a fluorenylene group; or

a phenylene group, an anthracenylene group, a pyrenylene group, or a fluorenylene group, each substituted with deuterium, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, or a tert-butyl group.

8. The organic light emitting device as claimed in claim 6 , wherein:

n1 or n2 is 1 or 2, and

the moieties represented by (L 1 ) n1 and (L 2 ) n2 are each independently represented by one of Formula 3-1, 3-2, 3-5, 3-8 and 3-9, below:

in Formula 3-1, 3-2, 3-5, 3-8 and 3-9 above, ** is a binding site to an anthracene core, and * is a binding site to Ar 1 or Ar 2 .

9. The organic light emitting device as claimed in claim 1 , wherein the anthracene-based compound represented by Formula 1 is represented by one of Formula 1b to 1d below:

wherein, in Formulae 1b to 1d above,

L 1 and L 2 are each independently defined the same as L of Formula 1;

n1 and n2 are each independently an integer of 1 or 2; and

Ar 1 and Ar 2 are each independently defined the same as Ar of Formula 1.

10. The organic light emitting device as claimed in claim 1 , wherein the anthracene-based compound represented by Formula 1 is one of Compound 112 to Compound 126 and Compound 128 to Compound 134, below:

11. The organic light-emitting device as claimed in claim 1 , wherein the organic layer includes:

a hole-transporting region between the first electrode and the emission layer, the hole-transporting region including at least one of a hole-injecting layer, a hole-transporting layer, a functional layer having both hole-injecting and hole-transporting capabilities, a buffer layer, and an electron blocking layer, and

an electron-transporting region between the emission layer and the second electrode, the electron-transporting region including at least one of a hole-blocking layer, an electron-transporting layer, and an electron-injecting layer.

12. The organic light-emitting device as claimed in claim 1 , wherein:

the emission layer further includes a dopant, and

the anthracene-based compound is a host.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 14, 2014
From: KIM, YOUNG-KOOK; HWANG, SEOK-HWAN; JUNG, HYE-JIN; PARK, JUN-HA; KIM, JONG-WOO; LEE, EUN-YOUNG; LIM, JIN-O; HAN, SANG-HYUN; JEONG, EUN-JAE; KIM, KWANG-HYUN; KIM, SOO-YON
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 032664/0105 →
Priority Claims (1)
KR 10-2013-0096897 · Aug 14, 2013 · national
Continuity (1)
Related Publication 20150048321A1 · Feb 19, 2015