IP Library Granted Patent US 10,069,086
Granted Patent B2
US 10,069,086 · App. 15/503,742 · Granted Sep 4, 2018

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

Inventors: Bitnari Kim (Cheonan, KR); Nam-Kyun Kim (Yongin, KR); Hong-Yeop Na (Seoul, KR); Tae-Jin Lee (Seoul, KR); Kyung-Hoon Choi (Hwaseong, KR); Jae-Hoon Shim (Seoul, KR); Young-Jun Cho (Seongnam, KR); Hee-Ryong Kang (Seoul, KR); Young-Mook Lim (Cheonan, KR); Hyun-Ju Kang (Gwangmyeong, KR); Doo-Hyeon Moon (Hwaseong, KR); Ji-Song Jun (Hwaseong, KR); Hee-Choon Ahn (Seoul, KR); Young-Kwang Kim (Hwaseong, KR); Jin-Ri Hong (Cheonan, KR)
Assignee: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
H01L51/0072C09K11/06H01L51/0058H01L51/0061H01L51/0067H01L51/0077C09K2211/1029C09K2211/181H01L51/001H01L51/0052H01L51/5016H01L51/5064H01L51/5072H01L51/5088H01L51/5092H01L51/56H01L2251/5384H01L2251/558
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Quick Facts
Patent No.
US 10,069,086
App. No.
15/503,742
Granted
Sep 4, 2018
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 excellent lifespan characteristics while maintaining high luminous efficiency.

Claims (23)

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, wherein the substituents on the substituted (C6-30)aryl group of A 1 and A 2 are—deuterium, a halogen, a unsubstituted (C1-C30)alkyl group, unsubstituted (C6-30)aryl group, 3- to 30-membered heteroaryl containing at least one hetero atom selected from O and S, a tri(C6-C30)arylsilyl, a tri(C1-C30)alkylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, an amino, a mono- or di(C1-C30)alkylamino, a mono- or di(C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a (C6-C30)aryl(C1-C30)alkyl, or a (C1-C30)alkyl(C6-C30)aryl;

L 1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;

X 1 to X 16 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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or are linked to an adjacent substituent(s) 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;

wherein

L represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;

X and Y each independently represent N or CR 17 ;

R 1 to R 17 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, 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, or a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl; or are linked to an adjacent substituent(s) 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; 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 , L 1 , and X 1 to X 16 are as defined in claim 1 .

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

L 1 is represented by one of the following formulas 7 to 19:

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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or are linked to an adjacent substituent(s) 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.

4. The organic electroluminescent device according to claim 1 , wherein formula 2 is represented by formula 20 or 21:

wherein

L and R 1 to R 17 are as defined in claim 1 .

5. The organic electroluminescent device according to claim 1 , wherein the substituents of the substituted alkyl, the substituted alkenyl, the substituted alkynyl, the substituted cycloalkyl, the substituted aryl(ene), the substituted heteroaryl, the substituted trialkylsilyl, the substituted triarylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted mono- or di-arylamino, the substituted alkylarylamino, and the substituted mono- or polycyclic, alicyclic or aromatic ring in L 1 , X 1 to X 16 , L, and R 1 to R 17 each independently are at least one selected from the group consisting of deuterium; a halogen; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30) alkenyl; a (C2-C30) alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a 3- to 7-membered heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a 3- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl; a (C6-C30)aryl unsubstituted or substituted with a cyano, a 3- to 30-membered heteroaryl, or a tri(C6-C30)arylsilyl; a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di-(C1-C30)alkylamino; a mono- or di-(C6-C30)arylamino; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl.

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

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

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2018
From: KIM, BIT-NA-RI; KIM, NAM-KYUN; NA, HONG-YEOP; LEE, TAE-JIN; CHOI, KYUNG-HOON; SHIM, JAE-HOON; CHO, YOUNG-JUN; KANG, HEE-RYONG; KANG, HYUN-JU; MOON, DOO-HYEON; JUN, JI-SONG; AHN, HEE-CHOON; KIM, YOUNG-KWANG; HONG, JIN RI; LIM, YOUNG-MOOK
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 046470/0888 →
Priority Claims (3)
KR 10-2014-0108415 · Aug 20, 2014 · national
KR 10-2015-0003430 · Jan 9, 2015 · national
KR 10-2015-0116757 · Aug 19, 2015 · national
Continuity (1)
Related Publication 20170279056A1 · Sep 28, 2017