Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-2023329089-A1
Application number	US-202318192310-A
Country	US
Kind code	A1
Filing date	Mar 29, 2023
Priority date	Apr 7, 2022
Publication date	Oct 12, 2023
Grant date	—

Abstract

A compound of Formula I,

is provided. In Formula I, moiety A and moiety B are monocyclic rings or polycyclic ring structures; X 1 and X 2 are C or N; each R A , R B , R C , R D , R E , R F , and R X is hydrogen or a substituent; at least one of R A , R B , R C , R D , R E , R F , and R X comprises a silyl group; if n=1, then R D is joined with R F to form a ring; if n=0 and m=1, then R D is joined with either R E or R A to form a ring, with the proviso that if R D is joined to R A , then R X is a substituted or unsubstituted aryl or heteroaryl group; and if n=0 and m=0, then the compound has the structure of Formula V,

Formulations, OLEDs, and consumer products comprising the compound are also provided.

First claim

What is claimed is:

1 . A compound of Formula I,

wherein:
each of moiety A and moiety B is independently a monocyclic 5-membered or 6-membered ring or a polycyclic ring system comprising 5-membered and/or 6-membered rings;
X 1 and X 2 are each independently C or N;
R A , R B , R C , and R F each independently represents mono to the maximum allowable number of substitutions, or no substitution;
each R A , R B , R C , R D , R E , R F , and R X is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, boryl, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
any two of R A , R B , R C , R D , R E , R F , and R X can be joined or fused to form a ring;
at least one of R A , R B , R C , R D , R E , R F , and R X comprises a silyl group;
each of n and m is independently 0 or 1;
if n=1, then R D is joined with R F to form a ring;
if n=0 and m=1, then R D is joined with either R E or R A to form a ring, with the proviso that if R D is joined to R A , then R X is a substituted or unsubstituted aryl or heteroaryl group;
if n=0 and m=0, then the compound has the structure of Formula V,

wherein each of X 6 to X 13 is independently C or N;
at least one of X 6 or X 13 is C and is bonded to a silyl group; and
any two of R A , R B , R C , and R X can be joined or fused to form a ring,

with the proviso that if moiety A and moiety B are 6-membered rings and each of R D and R E is a substituted or unsubstituted 6-membered ring then the following conditions are true:
(i) R X is a substituted or unsubstituted aryl or heteroaryl group;
(ii) R X does not join with R C to form a ring;
(iii) when R D is joined with R E or R F to form a 5-membered ring, the compound of Formula I does not comprise a triazine; and
(iv) when n=1, R X does not join with R B or R C to form a ring and at least one of R A , R B , R C , R D , R F , and R X comprises a silyl group.

2 . The compound of claim 1 , wherein each R A , R B , R C , R D , R E , R F , and R X is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, and combinations thereof.

3 . The compound of claim 1 , wherein the compound has a structure selected from the group consisting of

wherein:
moiety D is independently a 5-membered or 6-membered ring or a polycyclic ring system comprising 5-membered and/or 6-membered rings;
wherein X 3 , X 4 , and X 5 are each independently C or N;
R D′ and R E′ each independently represents mono to the maximum allowable number of substitutions, or no substitution;
each R D′ , R E′ , and R G is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, boryl, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
at least one of R A , R B , R C , R D , R E , R F , R X , and R Y comprises a silyl group;
any two of R A , R B , R C , R D , R D′ , R E , R E′ , R F , R G , and R X can be joined or fused to form a ring;
if moiety B and moiety D are both present and 6-membered rings, then R X is a substituted or unsubstituted aryl or heteroaryl group and R X does not join with R C to form a ring;
if moiety B and moiety C are both present and 6-membered rings, then R X is a substituted or unsubstituted aryl or heteroaryl group and R X does not join with R B or R C to form a ring, with the proviso that compounds of Formula II or Formula III do not include triazine.

4 . The compound of claim 1 , wherein moiety A is benzene; and/or moiety B is benzene.

5 . The compound of claim 1 , wherein R X is a substituted or unsubstituted phenyl.

6 . The compound of claim 1 , wherein R X comprises a substituted or unsubstituted carbazole.

7 . The compound of claim 1 , wherein R X comprises a silyl moiety.

8 . The compound of claim 1 , wherein at least one R B comprises a silyl group; and/or
at least one R c comprises a silyl group; and/or at least one R D′ comprises a silyl group.

9 . The compound of claim 1 , wherein at least one of R A , R B , R C , R D , R E , R F , and R X comprises a silyl group having the structure SiQ 1 Q 2 Q 3 ,
wherein each of Q 1 , Q 2 , and Q 3 is independently a substituted or unsubstituted 5-membered or 6-membered carbocyclic or heterocyclic ring; or wherein each of Q 1 , Q 2 , and Q 3 is independently an aryl or heteroaryl ring.

10 . The compound of claim 9 , wherein each of Q 1 , Q 2 , or Q 3 is phenyl.

11 . The compound of claim 1 , wherein the compound is selected from the group consisting of:

wherein:
S A , R 1 , R 2 , R 3 , R 4 , and R 5 each independently represents mono up to the maximum allowable number of substitutions, or no substitution;
at least one S A comprises a silyl group;
R AA represents aryl or heteroaryl, which may be further substituted by one or more R 6 ;
Y A is selected from the group consisting of BR′, BR′R″, NR′, PR′, P(O)R′, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO 2 , CR′, CR′R″, SiR′R″, Ge

Assignees

• Universal Display Corp

Inventors

• Fleetham Tyler
• Wolohan Peter
• Feldman Jerald
• Chen Hsiao-Fan
• Thompson Nicholas J
• Sheina Elena
• Jradi Fadi M
• Talluri Siva Kumar
• Idris Muazzam
• Paudyal Mahesh

Classifications

• H10K85/40 Primary

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• H10K50/12

  comprising dopants · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F7/0812 Primary

  comprising a heterocyclic ring · CPC title

• C07B2200/05

  Isotopically modified compounds, e.g. labelled · CPC title