US 12,004,420 B2
Organic electroluminescent compound and organic electroluminescent device comprising the same
Doo-Hyeon Moon, Gyeonggi-do (KR); Su-Hyun Lee, Gyeonggi-do (KR); Jin-Ri Hong, Gyeonggi-do (KR); So-Young Jung, Gyeonggi-do (KR); Dong-Hyung Lee, Gyeonggi-do (KR); and Sang-Hee Cho, Gyeonggi-do (KR)
Assigned to Rohm and Haas Electronic Materials Korea Ltd., (KR)
Filed by ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD., Chungcheongnam-do (KR)
Filed on May 29, 2020, as Appl. No. 16/886,822.
Claims priority of application No. 10-2019-0078837 (KR), filed on Jul. 1, 2019; and application No. 10-2020-0051436 (KR), filed on Apr. 28, 2020.
Prior Publication US 2021/0005822 A1, Jan. 7, 2021
Int. Cl. H10K 85/60 (2023.01)
CPC H10K 85/654 (2023.02) [H10K 85/622 (2023.02); H10K 85/633 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02)] 6 Claims
 
1. A plurality of host materials comprising at least one first host material comprising an organic electroluminescent compound represented by the following formula 1-1 or 1-2 and at least one second host material, which is different from the first host material, wherein the second host material comprises the compound represented by the following formula 100:

OG Complex Work Unit Chemistry
wherein,
R1 and R2 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a ring;
R3, Ra and Rb each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)heteroaryl where the (C3-C30)heteroaryl group is selected from the group consisting of furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizidinyl, acrylidinyl, silafluorenyl and germafluorenyl, 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, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino;
L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;
ETU is selected from any one of the substituents listed in the following Group 1;

OG Complex Work Unit Chemistry
Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (C3-C30)heteroaryl X represents CR11R12, O, or S;
R11 and R12 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted C3-C30)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a ring;
p represents an integer of 1 to 4, and when p is 2 or more, each R3 may be the same or different;
r represents an integer of 1 or 2, when r is 2, each Ra may be the same or different;
s represents an integer of 1 to 4, when s is 2 or more, each Rb may be the same or different; and
with the proviso that the compounds represented by the following formulas I-1 to I-3:

OG Complex Work Unit Chemistry
wherein,
R1, R2, and L1 are as defined in formula 1-1 and 1-2;
ETU1 to ETU3 are as defined as ETU in formula 1-1 and 1-2;
at least one of L1 and ETU1 include(s) triazine structure in formula I-1;
at least one of L1 and ETU2 include(s) pyridine structure, pyrimidine structure, or triazine structure in formula I-2; and
at least one of L1 and ETU3 include quinazoline structure in formula I-3, are excluded:

OG Complex Work Unit Chemistry
wherein,
V represents CX11X12, NX13, O or S;
L100 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (C3-C30)heteroarylene;
Ar100 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)heteroaryl, or -NX9X10;
X9 and X10 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (C3-C30)heteroaryl;
X11 to X13, X101 and X102 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)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, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(C3-C30)heteroarylamino, a substituted or unsubstituted (C1-C30)alkyl(C3-C30)heteroarylamino, a substituted or unsubstituted (C2-C30)alkenyl(C3-C30)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(C3-C30)heteroarylamino; and
j represents an integer of 1 to 4, k represents an integer of 1 to 6, and when j and k are 2 or more, each X101 and each X102 may be the same or different.