IP Library › Granted Patent US 12,652,949
Granted Patent B2
US 12,652,949 · App. 17/729,472 · Granted Jun 9, 2026

Electroluminescent device

Inventors: Zhihong Dai (Beijing, CN); Qiang Wang (Beijing, CN); Le Wang (Beijing, CN); Han Zhang (Beijing, CN); Junfei Wang (Beijing, CN); Menglan Xie (Beijing, CN); Cuifang Zhang (Beijing, CN); Nannan Lu (Beijing, CN); Qi Zhang (Beijing, CN); Dongdong Zhang (Beijing, CN); Xueyu Lu (Beijing, CN); Chuanjun Xia (Beijing, CN); Chi Yuen Raymond Kwong (Beijing, CN)
Assignee: BEIJING SUMMER SPROUT TECHNOLOGY CO., LTD.
H10K85/342C07F15/0033C09K11/06C09K2211/1033C09K2211/185H10K50/11H10K2101/10H10K2101/30
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Quick Facts
Patent No.
US 12,652,949
App. No.
17/729,472
Granted
Jun 9, 2026
Kind
B2
Abstract

Provided is an electroluminescent device. The organic electroluminescent device comprises an anode, a cathode and an organic layer disposed between the anode and the cathode, where the organic layer comprises a first compound having a structure of H-L 1 -E and a second compound having a general formula of M(L a ) m (L b ) n (L c ) q , and the device has at least one maximum emission wavelength greater than 630 nm. Such a new material composition consisting of the first compound and the second compound can be used in a light-emitting layer of the electroluminescent device. The new material composition can achieve the emission of deep red light in the device, significantly reduce a drive voltage of the device while significantly improving device efficiency and/or a device lifetime, and provide better device performance. Further provided is a display assembly.

Claims (704)

1 . An electroluminescent device comprising:

an anode,

a cathode, and

an organic layer disposed between the anode and the cathode, wherein the organic layer at least comprises a first compound and a second compound, and the device at least has one maximum emission wavelength greater than 630 nm;

wherein the first compound has a structure of H-L 1 -E, wherein H has a structure represented by Formula A:

wherein in Formula A,

Z 1 to Z 3 and Z 6 to Z 8 are, at each occurrence identically or differently, selected from CR z1 or N, Z 4 and Z 5 are, at each occurrence identically or differently, selected from CR z2 , and two substituents R z2 in Z 4 and Z 5 are joined to form a ring;

L 1 is selected from a single bond, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms or a combination thereof;

E is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;

R z1 is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof;

R z2 is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof; and

adjacent substituents R z1 , R z2 can be optionally joined to form a ring;

wherein the second compound is a metal complex and has a general formula of M(L a ) m (L b ) n , wherein M is selected from a metal with a relative atomic mass greater than 40, L a , L b are a first ligand and a second ligand coordinated to the metal M, respectively, m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, and m+n equals an oxidation state of the metal M; wherein when m is equal to 2 or 3, a plurality of L a may be identical or different; when n is equal to n to 2, two L b may be identical or different;

L a , L b can be optionally joined to form a multidentate ligand;

L a is, at each occurrence identically or differently, selected from a structure represented by any one of Formula 1-1-1, Formula 1-1-3, Formula 1-1-4, Formula 1-2-5, Formula 1-4 to Formula 1-14:

wherein

in Formula 1-1-1, X 3 to X 6 are, at each occurrence identically or differently, selected from CR x ;

in Formula 1-1-3, Formula 1-1-4, Formula 1-2-5, Formula 1-4 to Formula 1-14, X 1 to X 6 are, at each occurrence identically or differently, selected from CR x or N;

Y 1 to Y 6 are, at each occurrence identically or differently, selected from C, CR y or N;

B 1 to B 4 are, at each occurrence identically or differently, selected from CR b or N;

W 1 and W 2 are, at each occurrence identically or differently, selected from SiR w R w , GeR w R w , PR w , O, S or Se; wherein when two R w are present at the same time, the two R w may be identical or different;

R i , R ii and R iii represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;

X b and X c are, at each occurrence identically or differently, selected from the group consisting of: O, S, Se and NR N2 ;

G, R i , R ii , R ii , RN 2 , R b , R x , R y and R w are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof;

in Formula 1-1-1, Formula 1-2-5, at least one of X 3 to X 6 is selected from CR x , and the R x is, at each occurrence identically or differently, selected from the group consisting of: alkyl having 1 to 20 carbon atoms substituted with at least one cyano arylalkyl having 7 to 30 carbon atoms substituted with at least one cyano or halogen, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms and combinations thereof;

adjacent substituents G, R x , R y and R w can be optionally joined to form a ring; and

adjacent substituents R i , R ii , R iii , and R N2 ; can be optionally joined to form a ring.

2 . The electroluminescent device according to claim 1 , wherein in Formula A, the two substituents R z2 in Z 4 and Z 5 are joined to form a ring, and the ring has at least six ring atoms.

3 . The electroluminescent device according to claim 1 , wherein in the first compound, the H has a structure represented by any one of Formula A-1 to Formula A-8:

wherein in Formula A-1 to Formula A-8,

Z 1 to Z 3 and Z 6 to Z 8 are, at each occurrence identically or differently, selected from CR z1 or N;

Z h1 to Z h9 are, at each occurrence identically or differently, selected from CR zh or N;

Z m is selected from CR zm or N;

Z n is selected from CR zn R zn , O, S or NR zn ; wherein when Z n is selected from CR zn R zn , two R zn may be identical or different;

R z1 , R zh , R zm and R zn are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof; and

adjacent substituents R z1 , R zh , R zm , R zn can be optionally joined to form a ring.

4 . The electroluminescent device according to claim 3 , wherein in Formula A-1 to Formula A-8, R z1 , R zh , R zm and R zn are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group and combinations thereof; and

adjacent substituents R z1 , R zh , R zm , R zn can be optionally joined to form a ring.

5 . The electroluminescent device according to claim 1 , wherein the H is selected from the group consisting of the following structures:

wherein optionally, hydrogen in the structures of H-1 to H-76 can be partially or fully substituted with deuterium.

6 . The electroluminescent device according to claim 1 , wherein in the first compound, the E has a structure represented by Formula E-a or Formula E-b:

wherein in Formula E-a and Formula E-b,

E 1 to E 14 are, at each occurrence identically or differently, selected from C, CR e or N;

R e is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof;

adjacent substituents R e can be optionally joined to form a ring.

7 . The electroluminescent device according to claim 1 , wherein in the first compound, the E has a structure represented by any one of Formula E-1 to Formula E-10:

wherein in Formula E-1 to Formula E-10,

R A represents, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;

V is selected from O, S or Se;

R A is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof;

adjacent substituents R A can be optionally joined to form a ring.

8 . The electroluminescent device according to claim 7 , wherein in Formula E-1 to Formula E-21, the R A is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, a cyano group, a hydroxyl group, a sulfanyl group, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms and combinations thereof;

adjacent substituents R A can be optionally joined to form a ring.

9 . The electroluminescent device according to claim 7 , wherein at least one R A is present in Formula E-1 to Formula E-21, and the R A is, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, cyano, hydroxyl, a sulfanyl group, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms and combinations thereof;

adjacent substituents R A can be optionally joined to form a ring.

10 . The electroluminescent device according to claim 1 , wherein in the first compound, the E is selected from the group consisting of the following structures:

“ ” represents a position where the structure of E is joined to L 1 .

11 . The electroluminescent device according to claim 10 , wherein the L 1 is selected from the group consisting of the following structures:

wherein “*” represents a position where the structure of L 1 is joined to Formula H, and “ ” represents a position where the structure of L 1 is joined to E; and

optionally, hydrogen in the above structures of L-1 to L-22 can be partially or fully substituted with deuterium.

12 . The electroluminescent device according to claim 11 , wherein the first compound has the structure of H-L 1 -E, wherein the H is selected from any one of the group consisting of H-1 to H-76, the L 1 is selected from any one of the group consisting of L-0 to L-22, and the E is selected from any one of the group consisting of E-1 to E-38; optionally, hydrogen in the structure of the first compound can be partially or fully substituted with deuterium.

13 . The electroluminescent device according to claim 1 , wherein in Formula 1-1-1, Formula 1-1-3, Formula 1-1-4, Formula 1-2-5, and Formula 1-4 to Formula 1-14, X 1 to X 6 are, at each occurrence identically or differently, selected from CR x , and Y 1 to Y 6 are, at each occurrence identically or differently, selected from C or CR y .

14 . The electroluminescent device according to claim 1 , wherein in Formula 1-1-3, Formula 1-1-4, Formula 1-2-5, Formula 1-4 to Formula 1-14, at least one of X 1 to X 6 is selected from N.

15 . The electroluminescent device according to claim 1 , wherein in Formula 1-1-1, Formula 1-1-3, Formula 1-1-4, Formula 1-2-5, and Formula 1-4 to Formula 1-14, at least two adjacent substituents R y in Y 1 to Y 6 are joined to form a ring.

16 . The electroluminescent device according to claim 1 , wherein the L a is, at each occurrence identically or differently, selected from a structure represented by any one of Formula 1-1-1, Formula 1-1-4, Formula 1-2-5, Formula 1-5, and Formula 1-6 to Formula 1-8.

17 . The electroluminescent device according to claim 1 , wherein the L a is, at each occurrence identically or differently, selected from any one of the group consisting of Formula 1-1-1, Formula 1-1-3, Formula 1-1-4, Formula 1-2-5, Formula 1-5-1 to Formula 1-5-4, Formula 1-6-1, Formula 1-6-2, Formula 1-7-1, Formula 1-7-2, Formula 1-8-1, Formula 1-9-1 to Formula 1-9-3, Formula 1-10-1 to Formula 1-10-3, and Formula 1-12-1 to Formula 1-12-3:

wherein

in Formula 1-1-1, X 3 to X 6 are, at each occurrence identically or differently, selected from CR x ;

in Formula 1-1-3, Formula 1-1-4, Formula 1-2-5, Formula 1-5-1 to Formula 1-5-4, Formula 1-6-1 to Formula 1-6-2, Formula 1-7-1 to Formula 1-7-2, Formula 1-8-1, Formula 1-9-1 to Formula 1-9-3, Formula 1-10-1 to Formula 1-10-3, Formula 1-12-1 to Formula 1-12-3, X 1 to X 6 are, at each occurrence identically or differently, selected from CR x or N;

Y 1 to Y 5 are, at each occurrence identically or differently, selected from CR y or N;

B 1 to B 4 are, at each occurrence identically or differently, selected from CR b or N;

W 1 and W 2 are, at each occurrence identically or differently, selected from SiR w R w , GeR w R w , PR w , O, S or Se; wherein when two R w are present at the same time, the two R w may be identical or different;

G, R x , R y , R w , R b and R n3 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof;

in Formula 1-1-1, Formula 1-2-5, Formula 1-5-1 to Formula 1-5-4, Formula 1-6-1, Formula 1-6-2, Formula 1-7-1 and Formula 1-7-2, at least one of X 3 to X n is selected from CR x , wherein the X n corresponds to one of X 3 to X 6 that has the largest number in any one of Formula 1-1-1, Formula 1-2-5, Formula 1-5-1 to Formula 1-5-4, Formula 1-6-1, Formula 1-6-2, Formula 1-7-1 and Formula 1-7-2, and the R x is, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, cyano, isocyano and combinations thereof;

in Formula 1-6-1 and Formula 1-7-1, G is, at each occurrence identically or differently, selected from the group consisting of: NRR, OR and SR; wherein the R is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms and combinations thereof;

adjacent substituents G, R x , R y , R b , R w , R n3 , R can be optionally joined to form a ring.

18 . The electroluminescent device according to claim 1 , wherein in Formula 1-1-1, Formula 1-1-3, Formula 1-1-4, Formula 1-2-5, and Formula 1-4 to Formula 1-14, at least one or two of X 1 to X 6 are, at each occurrence identically or differently, selected from CR x , and/or at least one or two of Y 1 to Y 6 are, at each occurrence identically or differently, selected from CR y , wherein the R x and R y are, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof.

19 . The electroluminescent device according to claim 1 , wherein W 1 is, at each occurrence identically or differently, selected from O or S.

20 . The electroluminescent device according to claim 1 , wherein L a is, at each occurrence identically or differently, selected from the group consisting of the following structures:

wherein in the above structures, TMS is trimethylsilyl; and

optionally, hydrogen in the above structures can be partially or fully substituted with deuterium.

21 . The electroluminescent device according to claim 1 , wherein the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu.

22 . The electroluminescent device according to claim 1 , wherein the L b has the following structure:

R 1 to R 7 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof;

adjacent substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 can be optionally joined to form a ring.

23 . The electroluminescent device according to claim 20 , wherein L b is, at each occurrence identically or differently, selected from the group consisting of the following structures:

24 . The electroluminescent device according to claim 23 , wherein the second compound is an Ir complex and has a structure represented by any one of Ir(L a ) 2 (L b ), when the second compound has a structure of Ir(L a ) 2 L b , the L a is selected from any one or two of the group consisting of L a139 to L a152 , L a159 to L a168 , L a263 to L a452 , L a455 , L a457 , L a462 to L a464 , L a466 to L a468 , L a529 to L a673 , and the L b is selected from any one of the group consisting of L b1 to L b322 .

25 . The electroluminescent device according to claim 1 , wherein the organic layer is a light-emitting layer, the first compound is a host material, and the second compound is a light-emitting material.

26 . The electroluminescent device according to claim 1 , wherein the device emits red light or white light.

27 . A display assembly, comprising the electroluminescent device according to claim 1 .

28 . The electroluminescent device according to claim 1 , the two substituents R z2 in Z 4 and Z 5 are joined to form a ring, and the ring has at least seven ring atoms.

29 . The electroluminescent device according to claim 6 , wherein in Formula E-a, at least two of E 1 to E 6 are N; in Formula E-b, at least two of E 7 to E 14 are N.

30 . The electroluminescent device according to claim 1 , wherein in the first compound, the E has a structure represented by any one of Formula E-11 to Formula E-21:

wherein in Formula E-11 to Formula E-21,

R A represents, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;

V is selected from O, S or Se;

R A is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group and combinations thereof; and

adjacent substituents R A can be optionally joined to form a ring.

31 . The electroluminescent device according to claim 11 , wherein the first compound is selected from the group consisting of the following structures:

wherein optionally, hydrogen in the above structures can be partially or fully substituted with deuterium.

32 . The electroluminescent device according to claim 1 , wherein the L a is, at each occurrence identically or differently, selected from a structure represented by any one of Formula 1-1-4, Formula 1-2-5 and Formula 1-6.

33 . The electroluminescent device according to claim 17 , wherein in Formula 1-5-1 to Formula 1-5-4, Formula 1-6-1, Formula 1-6-2, Formula 1-7-1 and Formula 1-7-2, at least one of X 3 to X n is selected from CR x , wherein the X n corresponds to one of X 3 to X 6 that has the largest number in any one of Formula 1-5-1 to Formula 1-5-4, Formula 1-6-1, Formula 1-6-2, Formula 1-7-1 and Formula 1-7-2, and the R x is, at each occurrence identically or differently, selected from the group consisting of: halogen, cyano, alkyl having 1 to 20 carbon atoms substituted with at least one cyano or halogen, cycloalkyl having 3 to 20 ring carbon atoms substituted with at least one cyano or halogen, arylalkyl having 7 to 30 carbon atoms substituted with at least one cyano or halogen, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms and combinations thereof;

in Formula 1-6-1 and Formula 1-7-1, G is, at each occurrence identically or differently, selected from the group consisting of: NRR, OR and SR; wherein the R is, at each occurrence identically or differently, selected from the group consisting of: deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms and combinations thereof.

34 . The electroluminescent device according to claim 22 , wherein at least one or two of R 1 to R 3 are selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms or a combination thereof; and/or at least one of R 4 to R 6 is substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms or a combination thereof.

35 . The electroluminescent device according to claim 24 , the second compound is selected from the group consisting of Compound 27 to Compound 34, Compound 45 to Compound 86, Compound 115 to Compound 122, Compound 133 to Compound 174, Compound 203 to Compound 210, Compound 221 to Compound 262, Compound 266, Compound 268, Compound 270, Compound 272, Compound 274, Compound 276, Compound 278, Compound 280, Compound 282, Compound 284, Compound 286, Compound 288, Compound 290 to Compound 298, Compound 300, Compound 302, Compound 304, Compound 306, and Compound 309 to Compound 330, and wherein Compound 27 to Compound 34, Compound 45 to Compound 86, Compound 115 to Compound 122, Compound 133 to Compound 174, Compound 203 to Compound 210, Compound 221 to Compound 262, Compound 266, Compound 268, Compound 270, Compound 272, Compound 274, Compound 276, Compound 278, Compound 280, Compound 282, Compound 284, Compound 286, Compound 288, Compound 290 to Compound 298, Compound 300, Compound 302, Compound 304, Compound 306, and Compound 309 to Compound 330 have a general formula of Ir(L a ) 2 (L b ), wherein the two L a are identical, and the L a and L b correspond to structures shown in the following table, respectively:

Compound

Compound

Number

L a

L b

Number

L a

L b

27

L a139

L b31

28

L a139

L b88

29

L a140

L b31

30

L a140

L b88

31

L a141

L b31

32

L a141

L b88

33

L a163

L b31

34

L a163

L b88

45

L a263

L b31

46

L a263

L b88

47

L a264

L b31

48

L a264

L b88

49

L a271

L b31

50

L a271

L b88

51

L a272

L b31

52

L a272

L b88

53

L a276

L b31

54

L a276

L b88

55

L a278

L b31

56

L a278

L b88

57

L a296

L b31

58

L a296

L b88

59

L a300

L b31

60

L a300

L b88

61

L a302

L b31

62

L a302

L b88

63

L a307

L b31

64

L a307

L b88

65

L a322

L b31

66

L a322

L b88

67

L a334

L b31

68

L a334

L b88

69

L a337

L b31

70

L a337

L b88

71

L a347

L b31

72

L a347

L b88

73

L a347

L b31

74

L a347

L b88

75

L a360

L b31

76

L a360

L b88

77

L a361

L b31

78

L a361

L b88

79

L a374

L b31

80

L a374

L b88

81

L a433

L b31

82

L a433

L b88

83

L a440

L b31

84

L a440

L b88

85

L a450

L b31

86

L a450

L b88

115

L a139

L b122

116

L a139

L b126

117

L a140

L b122

118

L a140

L b126

119

L a141

L b122

120

L a141

L b126

121

L a163

L b122

122

L a163

L b126

133

L a263

L b122

134

L a263

L b126

135

L a264

L b122

136

L a264

L b126

137

L a271

L b122

138

L a271

L b126

139

L a272

L b122

140

L a272

L b126

141

L a276

L b122

142

L a276

L b126

143

L a278

L b122

144

L a278

L b126

145

L a296

L b122

146

L a296

L b126

147

L a300

L b122

148

L a300

L b126

149

L a302

L b122

150

L a302

L b126

151

L a307

L b122

152

L a307

L b126

153

L a322

L b122

154

L a322

L b126

155

L a334

L b122

156

L a334

L b126

157

L a337

L b122

158

L a337

L b126

159

L a347

L b122

160

L a347

L b126

161

L a347

L b122

162

L a347

L b126

163

L a360

L b122

164

L a360

L b126

165

L a361

L b122

166

L a361

L b126

167

L a374

L b122

168

L a374

L b126

169

L a433

L b122

170

L a433

L b126

171

L a440

L b122

172

L a440

L b126

173

L a450

L b122

174

L a450

L b126

203

L a139

L b135

204

L a139

L b139

205

L a140

L b135

206

L a140

L b139

207

L a141

L b135

208

L a141

L b139

209

L a163

L b135

210

L a163

L b139

221

L a263

L b135

222

L a263

L b139

223

L a264

L b135

224

L a264

L b139

225

L a271

L b135

226

L a271

L b139

227

L a272

L b135

228

L a272

L b139

229

L a276

L b135

230

L a276

L b139

231

L a278

L b135

232

L a278

L b139

233

L a296

L b135

234

L a296

L b139

235

L a300

L b135

236

L a300

L b139

237

L a302

L b135

238

L a302

L b139

239

L a307

L b135

240

L a307

L b139

241

L a322

L b135

242

L a322

L b139

243

L a334

L b135

244

L a334

L b139

245

L a337

L b135

246

L a337

L b139

247

L a347

L b135

248

L a347

L b139

249

L a347

L b135

250

L a347

L b139

251

L a360

L b135

252

L a360

L b139

253

L a361

L b135

254

L a361

L b139

255

L a374

L b135

256

L a374

L b139

257

L a433

L b135

258

L a433

L b139

259

L a440

L b135

260

L a440

L b139

261

L a450

L b135

262

L a450

L b139

266

L a263

L b245

268

L a264

L b245

270

L a271

L b245

272

L a272

L b245

274

L a276

L b245

276

L a278

L b245

278

L a296

L b245

280

L a300

L b245

282

L a302

L b245

284

L a307

L b245

286

L a322

L b245

288

L a334

L b245

290

L a337

L b245

291

L a139

L b245

292

L a347

L b245

293

L a140

L b245

294

L a347

L b245

295

L a141

L b245

296

L a360

L b245

297

L a163

L b245

298

L a361

L b245

300

L a374

L b245

302

L a433

L b245

304

L a440

L b245

306

L a450

L b245

309

L a529

L b122

310

L a529

L b126

311

L a529

L b88

312

L a529

L b135

313

L a584

L b122

314

L a584

L b126

315

L a584

L b88

316

L a584

L b135

317

L a666

L b31

318

L a666

L b126

319

L a666

L b122

320

L a666

L b88

321

L a667

L b31

322

L a667

L b126

323

L a667

L b122

324

L a668

L b31

325

L a668

L b126

326

L a668

L b122

327

L a668

L b88

328

L a669

L b31

329

L a669

L b122

330

L a669

L b126 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2022
From: DAI, ZHIHONG; WANG, QIANG; WANG, LE; ZHANG, HAN; WANG, JUNFEI; XIE, MENGLAN; ZHANG, CUIFANG; LU, NANNAN; ZHANG, QI; ZHANG, DONGDONG; LU, XUEYU; XIA, CHUANJUN; KWONG, CHI YUEN RAYMOND
To: BEIJING SUMMER SPROUT TECHNOLOGY CO., LTD.
Reel/Frame 059733/0777 →
Priority Claims (1)
CN 202110464195.5 · Apr 30, 2021 · national
Continuity (1)
Related Publication 20220393116A1 · Dec 8, 2022
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