IP Library Granted Patent US 10,749,119
Granted Patent B2
US 10,749,119 · App. 15/551,951 · Granted Aug 18, 2020

Plurality of host materials and organic electroluminescent device comprising the same

Inventors: Bitnari Kim (Anyang, KR); Sang-Hee Cho (Suwon, KR); Hee-Ryong Kang (Seoul, KR); Jin-Ri Hong (Bucheon, KR)
Assignee: Rohm and Haas Electronic Materials Korea Ltd
H01L51/0072C07D209/80C07D209/86C07D403/10C07D487/04C07D487/06C09K11/025C09K11/06H01L51/001H01L51/0052H01L51/0058H01L51/0067H01L51/0074C09K2211/1007C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/185H01L51/0085H01L51/5016H01L2251/5384
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Quick Facts
Patent No.
US 10,749,119
App. No.
15/551,951
Granted
Aug 18, 2020
Kind
B2
Abstract

The present disclosure relates to a plurality of host materials and organic electroluminescent device comprising the same. By comprising a specific combination of a plurality of host materials, the organic electroluminescent device of the present disclosure can show long lifespan while maintaining high luminous efficiency.

Claims (29)

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

wherein

A 1 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (5- to 30-membered)heteroaryl group, and A 1 may be linked to X 1 or X 8 , provided that, when formula 1 is represented by the following formula 5,

the (5- to 30-membered)heteroaryl of A 1 is selected from the group consisting of furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyrazinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl and benzodioxolyl;

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

X 1 to X 8 , and X 19 to X 26 , each independently, represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, —NR 5 R 6 , or SiR 7 R 8 R 9 ; or may be 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;

R 5 to R 9 , each independently, represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered)heteroaryl group; or may be 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 a second host compound is represented by the following formula 2:

wherein

X, Y and Z, each independently, represent N or CR 10 ; provided that at least one of X, Y and Z represent N;

L 2 represents a substituted or unsubstituted (C6-C30)arylene group;

R 1 to R 4 , each independently, represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, —NR 11 R 12 , or SiR 13 R 14 R 15 ;

R 10 to R 15 , each independently, represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered)heteroaryl group;

k and m, each independently, represent an inter of 1 to 5; and where k or m represents an integer of 2 or more, each of R 3 or R 4 may be the same or different; and

the heteroaryl and the heterocycloalkyl, each independently, contain 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 any one of the following formulae 3 to 5:

wherein

V and W represent a single bond or NR 16 ; provided that both V and W are not a single bond or NR 16 ;

R 16 represents hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered)heteroaryl group;

A 2 represents a substituted or unsubstituted (C6-C30)aryl group, and A 2 may be linked to X 14 or X 15 ;

L 3 and L 4 , each independently, represent a single bond, or a substituted or unsubstituted (C6-C30)arylene group;

X 9 to X 18 each independently, represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, —NR 5 R 6 , or —SiR 7 R 8 R 9 ; or may be 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;

A 1 , L 1 , X 1 to X 4 , X 7 , X 8 , X 19 to X 26 and R 5 to R 9 are as defined in claim 1 .

3. The organic electroluminescent device according to claim 1 , wherein L 2 in formula 2 is represented by any one of the following formulae 7 to 19:

wherein

Xi to Xp, each independently, represent hydrogen, deuterium, a halogen, a cyano 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 (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilylgroup, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or may be 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 the substituents of the substituted alkyl group, the substituted cycloalkyl group, the substituted cycloalkenyl group, the substituted heterocycloalkyl group, the substituted aryl(ene) group, the substituted heteroaryl group, and the substituted mono- or polycyclic, alicyclic or aromatic ring in A 1 , L 1 , L 2 , X 1 to X 8 , and R 1 to R 15 , each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; 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 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 mono- or di-(C1-C30)alkyl(C6-C30)aryl.

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

6. 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 Jun 16, 2020
From: KIM, BIT-NA-RI; KANG, HEE-RYONG; CHO, SANG-HEE; HONG, JIN-RI
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 052948/0320 →
Priority Claims (2)
KR 10-2015-0035281 · Mar 13, 2015 · national
KR 10-2016-0006579 · Jan 19, 2016 · national
Continuity (1)
Related Publication 20180033975A1 · Feb 1, 2018