IP Library Granted Patent US 11,130,747
Granted Patent B2
US 11,130,747 · App. 15/525,077 · Granted Sep 28, 2021

Plurality of host materials and an organic electroluminescence device comprising the same

Inventors: Jae-Hoon Shim (Seoul, KR); Kyoung-Jin Park (Seongnam, KR); Yoo-Jin Doh (Seoul, KR); Bitnari Kim (Cheonan, KR)
Assignee: Rohm and Haas Electronic Materials Korea Ltd
C07D403/10C07D403/14C07D405/14C07D409/14C07D487/04C07D495/04C07F7/0812C09K11/06H01L51/0067H01L51/0071H01L51/0072H01L51/0073H01L51/0085H05B33/14H01L51/5016H01L2251/5384
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Quick Facts
Patent No.
US 11,130,747
App. No.
15/525,077
Granted
Sep 28, 2021
Kind
B2
Abstract

The present invention relates to a plurality of host materials and an organic electroluminescent device comprising the same. By comprising a specific combination of a plurality of host compounds, the organic electroluminescent device according to the present invention provides high efficiency and long lifespan.

Claims (32)

1. An organic electroluminescent device comprising at least one light-emitting layer between an anode and a cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant; the host comprises plural host compounds; at least a first host compound of the plural host compounds is represented by the following formula 1; and a second host compound is represented by the following formula 2,

wherein

A 1 and A 2 each independently represent a substituted or unsubstituted (C6-C30)aryl;

n represents an integer of 0 or 1;

where n is 1, a 5-membered ring including Z 1 is fused with the phenyl ring of carbazole;

a 5-membered ring including Z 2 is fused with the phenyl ring of carbazole;

L 1 and La each independently represent a single bond, or a substituted or unsubstituted (C6-C30)arylene;

Z 1 and Z 2 each independently represent CR 1 R 2 , NR 3 , O, or S;

X 1 to X 6 , and R 1 to R 3 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or adjacent substituents may be linked to each other to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;

Ma represents a substituted or unsubstituted 5- to 30-membered nitrogen-containing heteroaryl;

Xa to Xh each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or adjacent substituents may be linked to each other to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;

a and d each independently represent an integer of 1 to 2, b and e each independently represent an integer of 1 to 3, c and f each independently represent an integer of 1 to 4, where a, b, c, d, e, or f is an integer of 2 or more, each of X 1 , each of X 2 , each of X 3 , each of X 4 , each of X 5 , and each of X 6 may be the same or different; and

the heteroaryl contains at least one hetero atom selected from B, N, O, S, Si, and P.

2. The organic electroluminescent device according to claim 1 , wherein formula 1 is represented by one of the following formulas 3 to 6:

wherein

A 1 , A 2 , Z 1 , Z 2 , L 1 , X 1 to X 6 , and a to fare as defined in claim 1 .

3. The organic electroluminescent device according to claim 1 , wherein formula 1 is represented by one of the following formulas 7 to 36:

wherein

A 1 , A 2 , Z 1 , L 1 , X 1 to X b , and a to fare as defined in claim 1 .

4. The organic electroluminescent device according to claim 1 , wherein in formulas 1 and 2, L 1 and La each independently represent a single bond, or one of the following formulas 37 to 49:

wherein

Xi to Xp each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or adjacent substituents may be linked to each other to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur.

5. The organic electroluminescent device according to claim 1 , wherein in formula 1,

A 1 and A 2 each independently represent phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, or fluoranthenyl.

6. The organic electroluminescent device according to claim 1 , wherein in formula 1,

X 1 to X 6 , and R 1 to R 3 each independently represent hydrogen, a substituted or unsubstituted (C6-C18)aryl, an unsubstituted triphenylsilyl, a substituted or unsubstituted dibenzothiophene, or a substituted or unsubstituted dibenzofuran.

7. The organic electroluminescent device according to claim 1 , wherein in formula 2,

Ma represents a monocyclic ring-type heteroaryl selected from the group consisting of a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted tetrazinyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted tetrazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyrimidinyl, and a substituted or unsubstituted pyridazinyl, or a fused ring-type heteroaryl selected from the group consisting of a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted isoindolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted indazolyl, a substituted or unsubstituted benzothiadiazolyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted cinnolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted carbazolyl, and a substituted or unsubstituted phenanthridinyl.

8. The organic electroluminescent device according to claim 1 , wherein in formula 2,

Xa to Xh each independently represent hydrogen; a cyano; a (C6-C15)aryl unsubstituted or substituted with a 10- to 20-membered heteroaryl or a tri(C6-C10)arylsilyl; a 10- to 20-membered heteroaryl unsubstituted or substituted with a (C6-C12)aryl or a cyano(C6-C12)aryl; or an unsubstituted tri(C6-C10)arylsilyl; or adjacent substituents may be linked to each other to form a substituted or unsubstituted benzene, a substituted or unsubstituted indole, a substituted or unsubstituted benzoindole, a substituted or unsubstituted indene, a substituted or unsubstituted benzofuran, or a substituted or unsubstituted benzothiophene.

9. The organic electroluminescent device according to claim 1 , wherein the compound represented by formula 1 is selected from the group consisting of:

10. The organic electroluminescent device according to claim 1 , wherein the compound represented by formula 2 is selected from the group consisting of:

Assignments (2)
CHANGE OF NAME Recorded Oct 17, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS KOREA LTD
To: DUPONT SPECIALTY MATERIALS KOREA LTD
Reel/Frame 069185/0438 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 13, 2018
From: SHIM, JAE-HOON; DOH, YOO JIN; PARK, KYOUNG-JIN; KIM, BIT-NA-RI
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 047482/0029 →
Priority Claims (2)
KR 10-2014-0156301 · Nov 11, 2014 · national
KR 10-2015-0157677 · Nov 10, 2015 · national
Continuity (1)
Related Publication 20170342057A1 · Nov 30, 2017