US2017331054A1PendingUtilityA1
Luminescent diazabenzimidazole carbene metal complexes
Est. expiryJul 31, 2033(~7 yrs left)· nominal 20-yr term from priority
Inventors:Peter MurerGlauco BattagliarinKorinna DormannStefan MetzGerhard WagenblastFlavio Luiz BeneditoSoichi WatanabeChristian LennartzThomas Gessner
C09K 2211/1007C09K 2211/185H01L 51/5056H01L 51/5096H01L 51/5016C09K 2211/1044C07F 15/0033H01L 51/0085C09K 11/06C09K 2211/1088H10K 50/181H10K 85/342H10K 2101/10H10K 50/18H10K 85/6572H10K 50/15H10K 85/6574H10K 50/11Y02E10/549H05B 33/14C09K 2211/1092C09K 2211/1059C07F 15/0086Y02P70/50C09K 11/025C07F 5/025
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Claims
Abstract
The present invention relates to metal-carbene complexes of the general formula to organic electronic devices, especially OLEDs (Organic Light-Emitting Diodes) which comprise such complexes, to an apparatus selected from the group consisting of illuminating elements, stationary visual display units and mobile visual display units comprising such an OLED, to the use of such a metal-carbene complex in OLEDs, for example as emitter, matrix material, charge transport material and/or charge or exciton blocker
Claims
exact text as granted — not AI-modified1 .- 23 . (canceled)
24 . A metal-carbene complex of the general formula
M is Pt;
m is 1, or 2; o is 0, or 1; and the sum of m and o is 2;
L is a monoanionic bidentate ligand;
R is a group of formula
R′ is hydrogen, C 1 -C 8 alkyl group, or a fluoroC 1 -C 4 alkyl group;
R 1 is hydrogen, a C 1 -C 8 alkyl group, a fluoroC 1 -C 4 alkyl group, or a C 3 -C 6 cycloalkyl group;
R 2 is hydrogen, a C 1 -C 8 alkyl group, a fluoroC 1 -C 4 alkyl group, or a C 3 -C 6 cycloalkyl group;
R 3 , R 3′ and R 3″ are independently of each other hydrogen; a C 1 -C 18 alkyl group, which can optionally be substituted by E and/or interrupted by D; a C 3 -C 12 cycloalkyl group, which can optionally be substituted by G; a C 3 -C 10 heterocycloalkyl radical which is interrupted by at least one of O, S and NR 65 and/or substituted by E; a C 6 -C 14 aryl group, which can optionally be substituted by G; or a C 2 -C 30 heteroaryl group, which can optionally be substituted by G; a halogen atom, CF 3 , CN, or SiR 80 R 81 R 82 ;
R 3 and R 3′ , or R 1 and R 3′ together form a group of formula
wherein X is O, S, NR 75 or CR 73 R 74 ;
R 4 , R 4′ and R 5 are independently of each other hydrogen; a C 1 -C 18 alkyl group, which can optionally be substituted by E and/or interrupted by D; a C 3 -C 12 cycloalkyl group, which can optionally be substituted by G; a C 3 -C 10 heterocycloalkyl radical which is interrupted by at least one of O, S and NR 65 and/or substituted by E; a C 6 -C 14 aryl group, which can optionally be substituted by G; or a C 2 -C 30 heteroaryl group, which can optionally be substituted by G; a halogen atom, CF 3 , CN, or SiR 80 R 81 R 82 ; or
R 4 and R 4′ together form a group of formula, or
R 6 and R 7 are independently of each other hydrogen, a C 1 -C 8 alkyl group, optionally interrupted by at least one heteroatom selected from —O—, —S— and —NR 65 —, optionally bearing at least one substituent, which is selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 alkoxy, halogen, and C 1 -C 8 haloalkyl; a C 3 -C 6 cycloalkyl group, optionally bearing at least one substituent, which is selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 alkoxy, halogen, and C 1 -C 8 haloalkyl; a heteroC 3 -C 6 cyclo alkyl group, interrupted by at least one heteroatom selected from —O—, —S— and —NR 65 —, optionally bearing at least one substituent, which is selected from C 1 -C 8 alkyl, C 1 -C 8 alkoxy, halogen, and C 1 -C 8 haloalkyl; or a C 6 -C 14 arylgroup, which can optionally be substituted by one, or two C 1 -C 8 alkyl groups; or
R 6 and R 7 form together a ring
wherein A 21 , A 21′ , A 22 , A 22′ , A 23 , A 23′ , A 24′ and A 24 are independently of each other hydrogen, a C 1 -C 4 alkyl group, a C 3 -C 6 cycloalkyl group, or a fluoroC 1 -C 4 alkyl group;
D is —CO—, —COO—, —S—, —SO—, —SO 2 —, —O—, —NR 65 —, —SiR 70 R 71 —, —POR 72 —, —CR 63 ═CR 64 — or —C≡C;
E is —OR 69 , —SR 69 , —NR 65 R 66 , —COR 68 , —COOR 67 , —CONR 65 R 66 , —CN, or F;
G is E; or a C 1 -C 18 alkyl group; a C 6 -C 14 aryl group, which is optionally substituted by a substituent selected from the group consisting of F, C 1 -C 18 alkyl, which is optionally substituted by F and C 1 -C 18 alkyl, which is interrupted by O; a C 2 -C 10 heteroaryl group; or a C 2 -C 10 heteroaryl group, which is substituted by a substituent selected from the group consisting of F, C 1 -C 18 alkyl, which is optionally substituted by F, SiR 80 R 81 R 82 , and C 1 -C 18 alkyl, which is interrupted by O;
R 63 and R 64 are independently of each other hydrogen; a C 6 -C 18 aryl group, which is optionally substituted by a substituent selected from the group consisting of C 1 -C 18 alkyl and C 1 -C 18 alkoxy; or a C 1 -C 18 alkyl group, which is optionally interrupted by —O—;
R 65 and R 66 are independently of each other a C 6 -C 18 aryl group, which is optionally substituted by a substituent selected from the group consisting of C 1 -C 18 alkyl and C 1 -C 18 alkoxy; or a C 1 -C 18 alkyl group, which is optionally interrupted by —O—; or
R 65 and R 66 together form a 5-membered ring or 6-membered ring;
R 67 is a C 6 -C 18 aryl group, which is optionally substituted by a substituent selected from the group consisting of C 1 -C 18 alkyl and C 1 -C 18 alkoxy; or a C 1 -C 18 alkyl group which is optionally interrupted by —O—,
R 68 is hydrogen; a C 6 -C 18 aryl group, which is optionally substituted by a substituent selected from the group consisting of C 1 -C 18 alkyl and C 1 -C 18 alkoxy; or a C 1 -C 18 alkyl group, which is optionally interrupted by —O—;
R 69 is a C 6 -C 18 aryl group, which is optionally substituted by a substituent selected from the group consisting of C 1 -C 18 alkyl and C 1 -C 18 alkoxy; or a C 1 -C 18 alkyl group, which is optionally interrupted by —O—;
R 70 and R 71 are independently of each other a C 1 -C 18 alkyl group; or a C 6 -C 18 aryl group, which is optionally substituted by C 1 -C 18 alkyl; and
R 72 is a C 1 -C 18 alkyl group; or a C 6 -C 18 aryl group, which is optionally substituted by C 1 -C 18 alkyl;
R 73 and R 74 are independently of each other hydrogen; a C 1 -C 25 alkyl group, which is optionally interrupted by —O—; a C 7 -C 25 arylalkyl group; a C 6 -C 24 aryl group, which is optionally substituted by C 1 -C 18 alkyl; or a C 2 -C 20 heteroaryl group, which is optionally substituted by C 1 -C 18 alkyl; or
R 73 and R 74 together form a 5-membered ring or 6-membered ring, which is optionally substituted by a C 1 -C 18 alkyl group, which is optionally interrupted by —O—, or
R 73 and R 74 together form a group of formula ═CR 76 R 77 , wherein
R 76 and R 77 are independently of each other hydrogen; a C 1 -C 18 alkyl group, which is optionally interrupted by O; a C 6 -C 24 aryl group, which is optionally substituted by C 1 -C 18 alkyl; or a C 2 -C 20 heteroaryl group, which is optionally substituted by C 1 -C 18 alkyl; or
R 75 is a C 6 -C 18 aryl group which is optionally substituted by a substituent selected from the group consisting of C 1 -C 18 alkyl and C 1 -C 18 alkoxy; or a C 1 -C 18 alkyl group, which is optionally interrupted by —O—; and
R 80 , R 81 and R 82 are independently of each other a C 1 -C 25 alkyl group, which is optionally interrupted by —O—; a C 6 -C 14 aryl group, which is optionally substituted by C 1 -C 18 alkyl; or a C 2 -C 10 heteroaryl group, which is optionally substituted by C 1 -C 18 alkyl.
25 . The metal-carbene complex according to claim 24 , which is a metal carbene complex of formula (II):
wherein
R is a group of formula
and
R′ is hydrogen, or a C 1 -C 5 alkyl group.
26 . The metal complex according to claim 24 , which is a metal complex of formula (IIa), formula (IIb), or formula (IIc):
wherein
R is a group of formula
and
R 6 in formula (IIa) is a C 1 -C 8 alkyl group, optionally interrupted by at least one heteroatom selected from —O—, —S— and —NR 65 —, optionally bearing at least one substituent, which is selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 alkoxy, halogen, and C 1 -C 8 haloalkyl; a C 3 -C 6 cycloalkyl group, optionally bearing at least one substituent, which is selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 alkoxy, halogen, and C 1 -C 8 haloalkyl;
a heteroC 3 -C 6 cycloalkyl group, interrupted by at least one heteroatom selected from —O—, —S— and —NR 65 —, optionally bearing at least one substituent, which is selected from C 1 -C 8 alkyl, C 1 -C 8 alkoxy, halogen, and C 1 -C 8 haloalkyl; or a group of formula
wherein
(i) R 22 , R 23 , and R 24 are independently of each other a hydrogen or a C 1 -C 5 alkyl group, with the proviso that only one or two of R 22 , R 23 , and R 24 may be a C 1 -C 5 alkyl group;
(ii) R 25 , R 26 , and R 27 are independently of each other a hydrogen or a C 1 -C 5 alkyl group, with the proviso that only one or two of R 25 , R 26 , and R 27 may be a C 1 -C 5 alkyl group; or
R 6 and R 7 in formula (IIc) form together a ring
27 . The metal-carbene complex according to claim 24 , wherein:
R is a group of formula
wherein
R 1 and R 2 are independently of each other a C 1 -C 5 alkyl group, a cyclopentyl group or a cyclohexyl group; and
R 3 is hydrogen, C 1 -C 5 alkyl group, a group of formula
wherein
R 10 is hydrogen, or a C 1 -C 5 alkyl group;
R 11 is hydrogen, or a C 1 -C 5 alkyl group;
R 12 is a C 1 -C 5 alkyl group; and
R 12′ is a C 1 -C 5 alkyl group.
28 . The metal complex according to claim 24 , wherein R is a group of formula
wherein
R 2 is CF 3 , a C 1 -C 5 alkyl group, a cyclopentyl group or a cyclohexyl group;
R 3 is hydrogen, a C 1 -C 5 alkyl group, a cyclopentyl group or a cyclohexyl group; and
R 3′ is hydrogen, a C 1 -C 5 alkyl group, a cyclopentyl group or a cyclohexyl group; with the proviso that in case one of R 3 and R 3′ is a cyclopentyl group or a cyclohexyl group, the other is hydrogen.
29 . The metal complex according to claim 24 , wherein R is a group of formula
wherein
R 3 is hydrogen, or a C 1 -C 5 alkyl group;
R 3′ is hydrogen, a C 1 -C 5 alkyl group, a cyclopentyl group or a cyclohexyl group; and
R 3′ is hydrogen, a C 1 -C 5 alkyl group, a cyclopentyl group or a cyclohexyl group; with the proviso that if both R 3′ and R 3″ are independently a C 1 -C 5 alkyl group, a cyclopentyl group or a cyclohexyl group, then R 3 is hydrogen.
30 . The metal-carbene complex according to claim 24 , wherein
(i) R 4 is hydrogen, or a C 1 -C 5 alkyl group;
R 4′ is hydrogen; and
R 5 is hydrogen, or a C 1 -C 5 alkyl group; or
(ii) R 4 is hydrogen, or a C 1 -C 5 alkyl group; R 4′ is a group of
wherein
R 20 is hydrogen, or a C 1 -C 5 alkyl group;
R 21 is hydrogen, or a C 1 -C 5 alkyl group;
R 22 is a C 1 -C 5 alkyl group; and
R 22′ is a C 1 -C 5 alkyl group; and
R 5 is hydrogen, or a C 1 -C 5 alkyl group; or
(iii) R 4 is hydrogen;
R 4′ is a group of formula
wherein
R 22 and R 22′ are independently a C 1 -C 5 alkyl group; and
R 5 is hydrogen.
31 . The metal-carbene complex according to claim 24 , wherein
(i) R 4 is hydrogen; R 4′ is hydrogen, or a C 1 -C 5 alkyl group; and R 5 is hydrogen, or C 1 -C 5 alkyl group; or (ii) R 4 is hydrogen; R 4′ is hydrogen; and R 5 is a group of formula
wherein
R 20 is hydrogen, or a C 1 -C 5 alkyl group;
R 21 is hydrogen, or a C 1 -C 5 alkyl group;
R 22 is a C 1 -C 5 alkyl group; and
R 22′ is a C 1 -C 5 alkyl group.
32 . The metal-carbene complex according to claim 24 , wherein R 6 and R 7 are independently of each other hydrogen, a C 1 -C 8 alkyl group, or a C 3 -C 6 cycloalkyl group; or
R 6 and R 7 form together a ring
with the proviso that if one of R 6 and R 7 is a C 3 -C 6 cycloalkyl group, the other is hydrogen.
33 . The metal-carbene complex according to claim 24 , wherein L is
34 . The metal complex according to claim 24 , wherein L is formula (D′):
which is different from formula (D)
wherein
Z 1 and Z 2 are independently of each other N; or
Z 1 and Z 2 are independently of each other CH;
R* is R′;
R 54 is R 4 ;
R 54′ is R 4′ ;
R 55 is R 5 ;
R 56 is R 6 ; and
R 57 is R 7 ;
wherein each group R is the same within one metal-carbene complex.
35 . An organic electronic device comprising at least one metal-carbene complex according to claim 24 .
36 . A light-emitting layer comprising at least one metal-carbene complex according to claim 24 .
37 . An apparatus selected from the group consisting of a stationary visual display unit, an information panel, a mobile visual display unit, an illumination unit, a keyboard, an item of clothing, a piece of furniture, and a wallpaper comprising the organic electronic device according to claim 35 , or the emitting layer according to claim 36 .
38 . An apparatus selected from the group consisting of an electrophotographic photoreceptor, a photoelectric converter, an organic solar cell, a switching element, an organic light emitting field effect transistor, an image sensor, a dye laser and an electroluminescent device comprising the metal-carbene complex according to claim 24 .
39 . A process for preparing a metal-carbene complex of the formula (I) according to claim 24 :
wherein
m is 2, and
M, R, R′, R 4 , R 4′ , R 5 , R 6 and R 7 are as defined in claim 24 ;
which process comprises:
reacting a compound of formula (X):
wherein
X 1 is CI, Br, or I; and
m, M, R, R′, R 4 , R 4′ , R 5 , R 6 and R 7 are as defined in claim 24 ;
with a compound of the formula:
wherein:
Y is:
(a) —B(OH) 2 , —B(OY 1 ) 2 ,
wherein:
each Y 1 is independently a C 1 -C 10 alkyl group;
Y 2 is a C 2 -C 10 alkylene group;
Y 13 is hydrogen or a C 1 -C 10 alkyl group; and
Y 14 is hydrogen or a C 1 -C 10 alkyl group;
(b) —SnR 307 R 308 R 309 , wherein:
R 307 , R 308 and R 309 are independently hydrogen or C 1 -C 6 alkyl, wherein two C 1 -C 6 alkyl radicals may optionally form a common ring;
(c) ZnR 310 R 311 , wherein:
R 310 is halogen; and
R 311 is a C 1 -C 10 alkyl group, a C 6 -C 12 aryl group, or a C 2 -C 10 alkenyl group; or
(d) SiR 312 R 313 R 314 , wherein:
R 312 , R 313 and R 314 are independently halogen, or a C 1 -C 6 alkyl group; and
R 1 , R 2 , R 3 , R 3′ , and R 3″ are as defined in claim 24 .
40 . The process according to claim 39 , which process further comprises:
reacting a compound of formula (XI):
wherein:
m, M, R 1 , R 4 , R 4′ , R 5 , R 6 and R 7 are as defined in claim 39 ;
with a halogenating agent to obtain a compound of formula (X):
41 . A process for preparing metal carbene complexes, the process comprising contacting a compound comprising a metal with at least one ligand of formula (D):
wherein R, R′, R 4 , R 4′ , R 5 , R 6 and R 7 are as defined in claim 24 .Join the waitlist — get patent alerts
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