US 12,284,913 B2
Organic electroluminescent materials and devices
Lichang Zeng, Lawrenceville, NJ (US); Zeinab Elshenawy, Holland, PA (US); Walter Yeager, Yardley, PA (US); Alexey Borisovich Dyatkin, Ambler, PA (US); and Chuanjun Xia, Lawrenceville, NJ (US)
Assigned to Universal Display Corporation
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Dec. 22, 2021, as Appl. No. 17/559,306.
Application 17/559,306 is a continuation of application No. 16/802,869, filed on Feb. 27, 2020, granted, now 11,245,080.
Application 16/802,869 is a continuation of application No. 15/063,957, filed on Mar. 8, 2016, granted, now 10,593,890.
Claims priority of provisional application 62/274,520, filed on Jan. 4, 2016.
Claims priority of provisional application 62/254,299, filed on Nov. 12, 2015.
Claims priority of provisional application 62/245,578, filed on Oct. 23, 2015.
Claims priority of provisional application 62/143,370, filed on Apr. 6, 2015.
Prior Publication US 2022/0115601 A1, Apr. 14, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. H10K 85/60 (2023.01); C07D 405/14 (2006.01); C07D 487/04 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/16 (2023.01); H10K 85/30 (2023.01); H10K 101/00 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/6572 (2023.02) [C07D 405/14 (2013.01); C07D 487/04 (2013.01); C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 85/615 (2023.02); H10K 85/654 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 50/16 (2023.02); H10K 85/342 (2023.02); H10K 2101/10 (2023.02); H10K 2101/90 (2023.02)] 17 Claims
 
1. A compound having Formula I:

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wherein G is selected from the group consisting of:

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wherein L1 is a direct bond;
wherein Z1, Z2, and Z4 to Z38 are each independently selected from the group consisting of N and CR6;
wherein at least two of Z1, Z2, and Z4 represent CR6;
wherein Ar1 and Ar2 are each independently selected from the group consisting of aryl and heteroaryl;
wherein R1, R2, R3, R4, and R5 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two adjacent substituents can optionally join or fuse into a ring;
where each R6 is independently selected from the group consisting of a direct bond, hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two adjacent substituents can optionally join or fuse into a ring; and
wherein Ar1 and Ar2 each can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two adjacent substituents on Ar1 or Ar2 can optionally join or fuse into a ring;
provided that all of conditions (a) to (e) are met:
(a) R6 does not comprise a carbazole or triazine;
(b) when Z17 to Z32 are each CR6, then Ar2 does not comprise indolocarbazole, phenanthrene, biphenyl or terphenyl;
(c) when Z23 and Z26 together represent CR6, then the corresponding R6 groups do not represent a direct bond;
(d) when Z9 to Z16 are each CR6, then no adjacent groups R6 at Z9 to Z16 join or fuse into a ring and Ar1 is not unsubstituted triazine; and
(e) the compound is not represented by any of the following structures:

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