IP Library Patent Application 17716638
Patent Application
App. No. 17/716,638

ORGANIC LIGHT-EMITTING DIODES WITH FLUORESCENT AND PHOSPHORESCENT EMITTERS

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Patent No.
US None
App. No.
17/716,638
Abstract

A light emitting device includes a first electrode, a hole transporting layer in contact with the first electrode, a second electrode, an electron transporting layer in contact with the second electrode; and an emissive layer between the hole transporting layer and the electron transporting layer. The emissive layer includes a phosphorescent emitter, a fluorescent emitter, and a host, and the phosphorescent emitter harvests electrogenerated excitons and transfers energy to the fluorescent emitter.

Claims (113)

1 . A light emitting device comprising:

a first electrode;

a hole transporting layer in contact with the first electrode;

a second electrode;

an electron transporting layer in contact with the second electrode; and

a single emissive layer between the hole transporting layer and the electron transporting layer, the emissive layer comprising a phosphorescent emitter, a fluorescent emitter, and a host, wherein the phosphorescent emitter harvests electrogenerated excitons and transfers energy to the fluorescent emitter;

wherein the phosphorescent emitter comprises a luminophore comprising a six-membered chelation ring.

2 .- 6 . (canceled)

7 . The light emitting device of claim 1 , wherein the light emitting device is a fluorescent organic light emitting device.

8 . (canceled)

9 . The light emitting device of claim 1 , wherein the phosphorescent emitter comprises a compound of General Formula I:

wherein:

each of Y 1a , Y 1b , and Y 1c is independently O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, arylalkenyl, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to an adjacent ring structure, thereby forming a cyclic structure;

each of Y 2a , Y 2b , Y 2c , and Y 2d is independently N, NR 5 , or CR 6 , wherein each R 5 and R 6 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, or arylalkenyl;

each of Y 3a , Y 3b , Y 3c , Y 3d , Y 4a , Y 4b , Y 4c , and Y 4d is independently N, O, S, NR 7 , CR 8 , wherein each R 7 and R 8 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, aminoalkoxy, haloalkyl, arylalkyl, or arylalkenyl; or Z(R 9 ) 2 , wherein Z is C or Si, and wherein each R 9 is independently hydrogen, halogen, hydroxyl, thiol, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, or arylalkenyl;

each of m and n is independently 1 or 2; and

each independently represents partial or full unsaturation of the ring with which it is associated.

10 . The light emitting device of claim 9 , wherein:

m is 2

n is 2; and

one of the following conditions (i) to (iii) is satisfied:

(i) M is Pt or Pd; at least one of Y 1a and Y 1c is independently NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 ; Y 2b and Y 2c are C; and Y 3b and Y 4b are N;

(ii) M is Ir or Rh; Y 1a is NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 ; Y 2b is C; and Y 3b , Y 2c and Y 4b are N; or

(iii) M is Au; Y 1b is NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 ; Y 2b , Y 2c and Y 4b are C; and Y 3b is N.

11 . (canceled)

12 . (canceled)

13 . The light emitting device of claim 9 , wherein each of R 3 and R 4 is independently linked to an adjacent ring structure.

14 . The light emitting device of claim 9 , wherein one of the following conditions (i) to (iii) is satisfied:

M is Pt or Pd; at least one of Y 1b and Y 1c is independently NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein R 3 is covalently linked to at least one of Y 2a , Y 2d , Y 3d , and Y 4d to form a cyclic structure; and at least of one of Y 2a , Y 2d , Y 3d and Y 4d is C;

(ii) M is Ir or Rh; Y 1b is NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein R 3 is covalently linked to at least one of Y 2a and Y 3d to form a cyclic structure; and at least of one of Y 2a and Y 3d is C;

(iii) M is Au; at least of one of Y 2a and Y 3d is C; and Y 1b is NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein R 3 is covalently linked to at least one of Y 2a and Y 3d to form a cyclic structure.

15 . (canceled)

16 . (canceled)

17 . The light emitting device of claim 1 , wherein the phosphorescent emitter comprises a compound of General Formula II:

wherein:

M is Ir, Rh, Pt, Os, or Ru;

each of R 1 and R 2 is independently hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, or arylalkenyl;

each of Y 1a , Y 1b , Y 1c , Y 1d , and Y 1e is independently O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, arylalkenyl, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to an adjacent ring structure, thereby forming a cyclic structure;

each of Y 2a , Y 2b , Y 2c , and Y 2d is independently N, NR 5 , or CR 6 , wherein each of R 5 and R 6 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, or arylalkenyl;

each of Y 3a , Y 3b , Y 3c , Y 3d , Y 4a , Y 4b , Y 4c , and Y 4d is independently N, O, S, NR 7 , CR 8 , wherein each of R 7 and R 8 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, or arylalkenyl; or Z(R 9 ) 2 , wherein Z is C or Si, and wherein each R 9 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, or arylalkenyl;

in each of each of Y 5a , Y 5b , Y 5c , Y 5d , Y 6a , Y 6b , Y 6c , and Y 6d is independently N, O, S, or C 8 ;

each of m and n is independently 1 or 2; and

each independently represents partial or full unsaturation of the ring with which it is associated.

18 . The light emitting device of claim 17 , wherein:

M is Ir or Rh;

m is 2;

Y 2b and Y 2c are C;

Y 3b and Y 4b are N; and

at least one of Y 1b and Y 1c is NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 .

19 . The light emitting device of claim 17 , wherein each of R 3 and R 4 is independently linked to an adjacent ring structure.

20 . The light emitting device of claim 17 , wherein:

M is Ir or Rh;

at least of one of Y 2a , Y 2d , Y 3d and Y 4d is C; and

at least one of Y 1b and Y 1c is NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein R 3 is covalently linked to at least one of Y 2a , Y 2d , Y 3d and Y 4d , thereby forming a cyclic structure.

21 . The light emitting device of claim 1 , wherein the phosphorescent emitter is a compound of General Formula III:

wherein:

M is a metal cation with two positive charges selected from Pt (II) and Pd (II);

each E 1 , E 2 , and E 3 independently represents O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, arylalkenyl, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to a C or N, thereby forming a cyclic structure;

each C independently represents a substituted or unsubstituted aromatic ring or heterocyclic group wherein a carbon atom is coordinated to M; and

each N independently represents a substituted or unsubstituted heterocyclic group wherein a nitrogen atom coordinated to M.

22 . The light emitting device of claim 1 , wherein the phosphorescent emitter is a compound of General Formula IV:

wherein:

M is a metal cation with three positive charges selected from Au (III) and Ag (III);

each E 1 , E 2 , and E 3 independently represents O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, arylalkenyl, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to a C or N, thereby forming a cyclic structure;

each C independently represents a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to M; and

N represents a substituted or unsubstituted heterocyclic group wherein a nitrogen atom is coordinated to M.

23 . The light emitting device of claim 1 , wherein the phosphorescent emitter is a compound of General Formula V:

wherein:

M is a metal cation with one positive charge selected from Ir (I) and Rh (I);

each E 1 , E 2 , and E 3 independently represents O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, arylalkenyl, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to a C or N, thereby forming a cyclic structure;

C represents a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to M; and

each N independently represents a substituted or unsubstituted heterocyclic group wherein a nitrogen atom is coordinated to M.

24 . The light emitting device of claim 1 , wherein the phosphorescent emitter is a compound of General Formula VI:

wherein:

M is a metal cation with three positive charges selected from Ir (III), Rh (III), Co (III), Al (III), and Ga (III);

each of E 1 , E 2 , E 3 , and E 4 independently represents O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, arylalkenyl, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to a C or N, thereby forming a cyclic structure;

each C independently represents a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to M; and

each N independently represents a substituted or unsubstituted heterocyclic group, wherein a nitrogen atom coordinated to the metal.

25 . The light emitting device of claim 1 , wherein the phosphorescent emitter is a compound of one of General Formulas VII and VIII:

wherein:

M is a metal cation with three positive charges selected from Ir (III), Rh (III), Co (III), Al (III), or Ga (III);

each of E 1 , E 2 , E 3 , E 4 , and E 5 independently represents O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each of R 3 and R 4 is independently hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, hydroxyl, halogen, thiol, alkoxy, haloalkyl, arylalkyl, arylalkenyl, or R 2 and R 3 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to a C or N, thereby forming a cyclic structure;

each C independently represents a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to M; and

each N independently represents a substituted or unsubstituted heterocyclic group, wherein a nitrogen atom coordinated to M.

26 . The light emitting device of claim 1 , wherein the phosphorescent emitter is a compound of General Formula IX:

wherein:

M is a metal cation with four positive charges selected from Pd (IV) and Pt (IV);

each of E 1 , E 2 , E 3 , and E 4 independently represents O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, arylalkenyl, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to a C or N, thereby forming a cyclic structure;

each C independently represents a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to M; and

each N independently represents a substituted or unsubstituted heterocyclic group, wherein a nitrogen atom coordinated to M.

27 . The light emitting device of claim 1 , wherein the phosphorescent emitter is a compound of General Formula X:

wherein:

M is a metal cation with four positive charges selected from Pd (IV) and Pt(IV);

each of E 1 , E 2 , E 3 , E 4 , and E 5 independently represents O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, arylalkenyl, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to a C or N, thereby forming a cyclic structure;

each C independently represents a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to M; and

each N independently represents a substituted or unsubstituted heterocyclic group, wherein a nitrogen atom is coordinated to M.

28 . The light emitting device of claim 1 , wherein the phosphorescent emitter is a compound of General Formula XI:

wherein:

M is a metal cation with two positive charges selected from Ru (II) and Os (II);

each of E 1 , E 2 , E 3 , E 4 , and E 5 independently represents O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, arylalkenyl, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to a C or N, thereby forming a cyclic structure;

each C independently represents a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to M; and

each N independently represents a substituted or unsubstituted heterocyclic group, wherein a nitrogen atom is coordinated to M.

29 . The light emitting device of claim 1 , wherein the phosphorescent emitter is a compound of General Formula XII:

wherein:

M is a metal cation with two positive charges selected from Ru (II) and Os (II);

each of E 1 , E 2 , E 3 , and E 4 independently represents O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclic group, amino, alkoxy, haloalkyl, arylalkyl, arylalkenyl, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to a C or N, thereby forming a cyclic structure;

each C independently represents a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to M; and

each N independently represents a substituted or unsubstituted heterocyclic group, wherein a nitrogen atom is coordinated to M.

30 . The light emitting device of claim 1 , wherein the fluorescent emitter comprises one of the following compounds:

wherein:

each of R 1l , R 2l , R 3l , R 4l , R 5l , R 6l , R 7l and R 8l is independently hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric, or any conjugate or combination thereof, and

each of Y a , Y b , Y c , Y d , Y e , Y f , Y g , Y h , Y i , Y j , Y k , Y l , Y m , Y n , Y o , and Y p is independently C, N or B; and

each of U a , U b and U c is independently CH 2 , CRR, C═O, SiRR, GeH 2 , GeRR, NH, NR, PH, PR, RP═O, AsR, RAs═O, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , BH, BR, RBi═O, BiH, or BiR, wherein each R is independently is independently hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric, or any conjugate or combination thereof.