IP Library Patent Application 17214253
Patent Application
App. No. 17/214,253

PLURALITY OF HOST MATERIALS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

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Patent No.
US None
App. No.
17/214,253
Abstract

The present disclosure relates to a plurality of host materials comprising at least one first host compound and at least one second host compound, and an organic electroluminescent device comprising the same. By comprising a specific combination of the compounds wherein the first host compound is represented by formula 1 and the second host compound is represented by formula 2, it is possible to provide an organic electroluminescent device having improved driving voltage, luminous efficiency, power efficiency and/or lifetime property.

Claims (47)

1 . A plurality of host materials comprising at least one first host compound and at least second host compound, wherein the first host compound is represented by the following formula 1, and the second host compound is represented by the following formula 2:

wherein

B 1 to B 7 , each independently, are not present, or represent a substituted or unsubstituted (C5-C20) ring, in which carbon atoms of the ring may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur, with the proviso that at least five of B 1 to B 7 are present, and adjacent rings of B 1 to B 7 are fused with each other;

Y represents —N(L 1 -(Ar 1 ) n )—, —O—, —S—, or —C(R 1 )(R 2 )—;

L 1 represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;

Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or —N(R 3 )(R 4 );

R 1 to R 4 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a ring(s); and

n represents an integer of 1 or 2, where if n is 2, each of Ar 1 may be the same or different;

wherein

X represents —N═, —NR 35 —, —O— or —S—;

Z represents —N═, —NR 36 —, —O— or —S—, where if X represents —N═, Z represents —NR 36 —, —O— or —S—, and if X represents —NR 35 —, Z represents —N═, —O— or —S—;

HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl;

R 31 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;

R 32 to R 34 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, 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 tri(C6-C30)arylsilyl, or -L 3 -N(Ar 2 )(Ar 3 ); or may be linked to an adjacent substituent to form a ring(s);

R 35 and R 36 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, 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 tri(C6-C30)arylsilyl, or -L 3 -N(Ar 2 )(Ar 3 );

L 2 and L 3 , each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;

Ar 2 and Ar 3 , each independently, represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; and

a′ represents 1, b′ and c′, each independently, represent an integer of 1 or 2, and d′ represents an integer of 1 to 4, where if each of b′, c′ and d′ is an integer of 2 or more, each of R 32 to each of R 34 may be the same or different.

2 . The plurality of host materials according to claim 1 , wherein the substituents of the substituted alkyl, the substituted alkylene, the substituted alkenyl, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted cycloalkyl, the substituted cycloalkylene, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted fused ring of an aliphatic ring(s) and an aromatic ring(s), and the substituted ring, 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 50-membered)heteroaryl unsubstituted or substituted with at least one of a (C1-C30)alkyl(s), a (C6-C30)aryl(s), and a di(C6-C30)arylamino(s); a (C6-C30)aryl unsubstituted or substituted with at least one of deuterium, a cyano(s), a (C1-C30)alkyl(s), a (3- to 50-membered)heteroaryl(s), a mono- or di-(C6-C30)arylamino(s), and a tri(C6-C30)arylsilyl(s); 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-(C2-C30)alkenylamino; a mono- or di-(C6-C30)arylamino; a mono- or di-(3- to 30-membered)heteroarylamino; a (C1-C30)alkyl(C2-C30)alkenylamino; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkyl(3- to 30-membered)heteroarylamino; a (C2-C30)alkenyl(C6-C30)arylamino; a (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; a (C6-C30)aryl(3- to 30-membered)heteroarylamino; 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.

3 . The plurality of host materials according to claim 1 , wherein formula 1 is represented by at least one of the following formulas 1-1 to 1-4:

wherein

Y 1 , Y 2 , Y 3 , and Y 4 , each independently, are the same as the definition of Y in claim 1 , where if a plurality of Ar 1 's are present, each of Ar 1 may be the same or different;

X 1 to X 12 , each independently, represent —N═ or —C(R a )═; and

R a , each independently, represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or adjacent R a 's may be linked to each other to form a ring(s), where if a plurality of R a 's are present, each of R a may be the same or different.

4 . The plurality of host materials according to claim 3 , wherein at least one of Ar 1 (s) and R a (s), each independently, is at least one selected from those listed in the following group 1:

wherein

D1 and D2, each independently, represent a benzene ring or a naphthalene ring;

X 21 represents O, S, NR 5 , or C(R 6 )(R 7 );

X 22 , each independently, represents CR 8 or N, with the proviso that at least one of X 22 represents N;

X 23 , each independently, represents CR 9 or N;

L 11 to L 18 , each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;

R 11 to R 21 and R 5 to R 9 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl, or may be linked to an adjacent substituent to form a ring(s); and

aa, ff, and gg, each independently, represent an integer of 1 to 5, bb represents an integer of 1 to 7, and cc, dd, and ee, each independently, represent an integer of 1 to 4, where if each of aa to gg is an integer of 2 or more, each of R 11 to each of R 17 may be the same or different.

5 . The plurality of host materials according to claim 3 , wherein at least one of Ar 1 (s) and R a (s), each independently, is at least one selected from those listed in the following groups 2 and 3:

in group 2,

L represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene; and

A 1 to A 3 , each independently, represent a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl.

6 . The plurality of host materials according to claim 1 , wherein in formula 1, B 1 to B 7 , each independently, are not present, or represent a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted cyclopentadiene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted pyridine ring, or a substituted or unsubstituted dibenzofuran ring, with the proviso that at least five of B 1 to B 7 are present, and adjacent rings of B 1 to B 7 are fused with each other.

7 . The plurality of host materials according to claim 1 , wherein formula 2 is represented by at least one selected from the following formulas 2-1 to 2-8:

wherein

X, Z, HAr, R 31 to R 38 , L 2 and a′ to d′ are as defined in claim 1 ;

Z 1 to Z 5 and Z 11 to Z 17 , each independently, represent N or CR 37 ; and

R 37 , each independently, is the same as the definition of R 32 .

8 . The plurality of host materials according to claim 1 , wherein in formula 2, HAr represents a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted benzoquinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted benzoisoquinolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted triazanaphthyl, or a substituted or unsubstituted benzothienopyrimidinyl.

9 . The plurality of host materials according to claim 1 , wherein the compound represented by formula 1 is at least one selected from the following compounds:

10 . The plurality of host materials according to claim 1 , wherein the compound represented by formula 2 is at least one selected from the following compounds:

11 . An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one of the light-emitting layers comprises the plurality of host materials according to claim 1 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 23, 2025
From: JUNG, SO-YOUNG; JUN, JI-SONG; LEE, SU-HYUN; CHO, SANG-HEE; HONG, JIN-RI
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 072651/0083 →
CHANGE OF NAME Recorded Nov 11, 2024
From: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
To: DUPONT SPECIALTY MATERIALS KOREA LTD.
Reel/Frame 069316/0857 →