IP Library › Granted Patent US 8,932,731
Granted Patent B2
US 8,932,731 · App. 12/066,554 · Granted Jan 13, 2015

Compounds for organic electronic devices

Inventors: Amir Parham (Frankfurt, DE); Susanne Heun (Bad Soden, DE); Horst Vestweber (Gilserberg, DE); Philipp Stoessel (Frankfurt am Main, DE); Holger Heil (Darmstadt, DE); Rocco Fortte (Frankfurt, DE)
Assignee: Merck Patent GmbH
C09K11/06C07D471/16H01L51/0059H01L51/0071H01L51/0072H05B33/14C09B17/00C09B19/00C09B21/00C09B23/145C09B23/148C09B57/00C09B57/008C09K2211/1014C09K2211/1029H01L51/0052H01L51/0068H01L51/008H01L51/5012H01L51/5048Y02E10/549Y10S977/754
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Quick Facts
Patent No.
US 8,932,731
App. No.
12/066,554
Granted
Jan 13, 2015
Kind
B2
Abstract

The present invention relates to the improvement of organic electroluminescent devices, in particular blue-emitting devices, by using compounds of the formula (1) or formula (2) as dopants in the emitting layer or as hole-transport material in a hole-transport layer.

Claims (72)

1. An organic electroluminescent device comprising at least one compound of formula (1) and/or a compound of formula (2)

wherein

X is, identically or differently on each occurrence, N, P, As, Sb, P═, As═O, or Sb═O;

Y is, identically or differently on each occurrence, O, S, C(R 1 ) 2 , C═O, C═S, C═NR 1 , C═C(R 1 ) 2 , Si(R 1 ) 2 , BR 1 ,NR 1 , PR 1 , AsR 1 , SbR 1 , BiR 1 , P(═O)R 1 , As(═O)R 1 , Sb(═O)R 1 , Bi(═O)R 1 , SO, SeO, TeO, SO 2 , SeO 2 , TeO 2 , or a chemical bond;

R 1 is, identically or differently on each occurrence, H, OH, F, Cl, Br, I, CN, CHO, NO 2 , N(Ar) 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)Ar, P(═O)Ar 2 , S(═O)Ar, S(═O)Ar 2 , CR 2 ═CR 2 Ar, C≡CAr, OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having up to 40 C atoms optionally substituted by one or more radicals R 2 , a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)R 2 , S═O, SO 2 , NR 2 , —O—, —S—, or —CONR 2 — and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R 2 , or a combination of two, three, four or five of these systems; and wherein two or more substituents R 1 , either on the same ring or on different rings, optionally define a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;

R is, identically or differently on each occurrence, in the compound of formula (2), H, OH, F, Cl, Br, I, CN, CHO, NO 2 , N(Ar) 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)Ar, P(═O)Ar 2 , S(═O)Ar, S(═O)Ar 2 , CR 2 ═CR 2 Ar, C≡CAr, OSO 2 R 2 , a straight-chain alkyl group having up to 40 C atoms optionally substituted by one or more radicals R 2 , a branched or cyclic alkyl group having 3 to 40 C atoms optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by —R 2 C═CR 2 —, C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)R 2 , S═O, SO 2 , NR 2 , —O—, —S—, or —CONR 2 — and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , or a combination of two, three, four or five of these systems; and wherein two or more substituents R 1 , either on the same ring or on different rings, optionally define a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another; with the proviso that at least one radical R is not equal to hydrogen;

and

is, identically or differently on each occurrence in the compound of formula (1), H, CR 2 ═CR 2 Ar, C≡CAr, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , with the proviso that at least one radical R is not equal to hydrogen;

R 2 is, identically or differently on each occurrence, H or an aliphatic, aromatic, and/or heteroaromatic hydrocarbon radical having up to 20 C atoms, wherein two or more radicals R 2 optionally define a ring system with one another;

Ar is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5-30 aromatic ring atoms optionally substituted by one or more non-aromatic radicals R 1 ;

L is an at least divalent straight-chain alkylene, alkylidene, alkyleneoxy, or thioalkyleneoxy group having up to 40 C atoms optionally substituted by one or more radicals R 2 , or a branched or cyclic alkylene, alkylidene, alkyleneoxy or thioalkyleneoxy group having 3 to 40 C atoms optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by —CR 2 ═CR 2 —, C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)R 2 , S═O, SO 2 , —O—, —S—, or —CONR 2 — and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN, or NO 2 , an at least divalent aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , P(R 1 ) 3-p , P(═O)(R 1 ) 3-p , C(R 1 ) 4-p , Si(R 1 ) 4-p , N(Ar) 3-p , or a combination of two, three, four or five of these systems; or is a chemical bond;

n is, identically or differently on each occurrence, 0, 1, or 2, wherein when n =0, a hydrogen or R 1 is present instead of Y, with the proviso that at least two n are not equal to 0;

p is 2, 3, 4, 5, or 6, with the proviso that p is not greater than the maximum valency of L.

2. The organic electroluminescent device of claim 1 , wherein X is nitrogen, phosphorus, or P═O.

3. The organic electroluminescent device of claim 1 , wherein Y is, identically or differently on each occurrence, O, S, C(R 1 ) 2 , C═O, P(═O)R 1 , C═C(R 1 ) 2 , NR 1 , SO, SO 2 , or a chemical bond.

4. The organic electroluminescent device of claim 1 , wherein R 1 is, identically or differently on each occurrence, H, F, CF 3 , OCH 3 , OCF 3 , an aliphatic, aromatic, or heteroaromatic hydrocarbon radical having up to 10 C atoms, or in that R 1 on bridges Y stands for an aliphatic hydrocarbon radical having up to 6 C atoms or for an aryl or heteroaryl group having 6 to 10 C atoms, wherein two radicals R 1 on the same bridge Y optionally define a ring system with one another.

5. The organic electroluminescent device of claim 1 , wherein R is, identically or differently on each occurrence, CR 2 ═CR 2 Ar, C≡CAr, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, optionally substituted by one or more non-aromatic radicals R 2 .

6. The organic electroluminescent device of claim 1 , wherein L is —CR 2 ═CR 2 —, —C≡C—, C═O, S═O, SO 2 , —O—, —S—, P(R 1 ) 3-p , P(═O)(R 1 ) 3-p , C(R 1 ) 4-p , Si(R 1 ) 4-p , N(Ar) 3-p , or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, optionally substituted by one or more radicals R 2 , or a combination of two, three or four of these systems or a chemical bond.

7. An organic electroluminescent device comprising at least one compound of formula (1) and/or a compound of formula (2)

wherein

X is, identically or differently on each occurrence, N, P, As, Sb, P═O, As═O, or Sb═O;

Y is, identically or differently on each occurrence, O, S, C(R 1 ) 2 , C═O, C═S, C═NR 1 , C═C(R 1 ) 2 , Si(R 1 ) 2 , BR 1 , NR 1 , PR 1 , AsR 1 , SbR 1 , BiR l , P(═O)R 1 , As(═O)R 1 , Sb(═O)R 1 , Bi(═O)R 1 , SO, SeO, TeO, SO 2 , SeO 2 , TeO 2 , or a chemical bond;

R 1 is, identically or differently on each occurrence, H, OH, F, Cl, Br, I, CN, CHO, NO 2 , N(Ar) 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)Ar, P(═O)Ar 2 , S(═O)Ar, S(═O)Ar 2 , CR 2 ═CR 2 Ar, C≡CAr, OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having up to 40 C atoms optionally substituted by one or more radicals R 2 , a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)R 2 , S═O, SO 2 , NR 2 , —O—, —S—, or —CONR 2 — and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R 2 , or a combination of two, three, four or five of these systems; and wherein two or more substituents R′, either on the same ring or on different rings, optionally define a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another, or is a bond;

R is, identically or differently on each occurrence, H, OH, F, Cl, Br, I, CN, CHO, NO 2 , N(Ar) 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)Ar, P(═O)Ar 2 , S(═O)Ar, S(═O)Ar 2 , CR 2 ═CR 2 Ar, C≡CAr, OSO 2 R 2 , a straight-chain alkyl group having up to 40 C atoms optionally substituted by one or more radicals R 2 , a branched or cyclic alkyl group having 3 to 40 C atoms optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)R 2 , S═O, SO 2 , NR 2 , —O—, —S—, or —CONR 2 — and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , or a combination of two, three, four or five of these systems; and wherein two or more substituents either on the same ring or on different rings, optionally define a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another; with the proviso that at least one radical R is not equal to hydrogen, or is a bond;

R 2 is, identically or differently on each occurrence, H or an aliphatic, aromatic, and/or heteroaromatic hydrocarbon radical having up to 20 C atoms, wherein two or more radicals R 2 optionally define a ring system with one another;

Ar is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5-30 aromatic ring atoms optionally substituted by one or more non-aromatic radicals R 1 ;

L is an at least divalent straight-chain alkylene, alkylidene, alkyleneoxy, or thioalkyleneoxy group having up to 40 C atoms optionally substituted by one or more radicals R 2 , or a branched or cyclic alkylene, alkylidene, alkyleneoxy or thioalkyleneoxy group having 3 to 40 C atoms optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by —CR 2 ═CR 2 —, —C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)R 2 , S═O, SO 2 , —O—, —S—, or —CONR 2 — and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN, or NO 2 , an at least divalent aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , P(R 1 ) 3-p , P(═O)(R 1 ) 3-p , C(R 1 ) 4-p , Si(R 1 ) 4-p , N(Ar) 3-p , or a combination of two, three, four or five of these systems; or is a chemical bond;

n is, identically or differently on each occurrence, 0, 1, or 2, wherein when n =0, a hydrogen or R 1 is present instead of Y, with the proviso that at least two n are not equal to 0;

p is 2, 3, 4, 5, or 6, with the proviso that p is not greater than the maximum valency of L; and

with the proviso that said compound is not:

wherein said organic electroluminescent device comprises a polymer, oligomer, or dendrimer comprising at least one compound of formula (1) and/or compound of formula (2) as recurring units, wherein at least one R or R 1 of said at least one compound of formula (1) and/or compound of formula (2) is a bond to said polymer, oligomer, or dendrimer.

8. The organic electroluminescent device of claim 1 , wherein said organic electroluminescent device comprises an anode, a cathode, and at least one emitting layer, wherein said at least one emitting layer comprises at least one compound of formula (1) and/or a compound of formula (2).

9. The organic electroluminescent device of claim 8 , wherein said at least one compound of formula (1) and/or a compound of formula (2) is employed as a mixture with at least one host material and/or wherein said at least one compound formula (1) and/or compound of formula (2) is employed as hole-transport and/or hole-injection material.

10. A compound of formula (1) and/or a compound of formula (2)

wherein

X is, identically or differently on each occurrence, N, P, As, Sb, P═O, As═O, or Sb═O;

Y is, identically or differently on each occurrence, O, S, C(R 1 ) 2 , C═O, C═S, C═NR 1 , C═C(R 1 ) 2 , Si(R 1 ) 2 , BR 1 , NR 1 , PR 1 , AsR 1 , SbR 1 , BiR 1 , P(═O)R 1 , As(═O)R 1 , Sb(═O)R 1 , Bi(═O)R 1 , SO, SeO, TeO, SO 2 , SeO 2 , TeO 2 , or a chemical bond;

R 1 is, identically or differently on each occurrence, H, OH, F, Cl, Br, I, CN, CHO, NO 2 , N(Ar) 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)Ar, P(═O)Ar 2 , S(═O)Ar, S(═O)Ar 2 , CR 2 ═CR 2 Ar, C≡Car, OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having up to 40 C atoms optionally substituted by one or more radicals R 2 , a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)R 2 , S═O, SO 2 , NR 2 , —O—, —S—, or —CONR 2 — and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R 2 , or a combination of two, three, four or five of these systems; and wherein two or more substituents R 1 , either on the same ring or on different rings, optionally define a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;

R is, identically or differently on each occurrence in the compound of formula (1), H, CR 2 ═CR 2 Ar, C≡CAr, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 ; with the proviso that at least one radical R is not equal to hydrogen

and

is, identically or differently on each occurrence in the compound of formula (2), H, OH, F, Cl, Br, I, CN, CHO, NO 2 , N(Ar) 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)Ar, P(═O)Ar 2 , S(═O)Ar, S(═O)Ar 2 , CR 2 ═CR 2 Ar, C≡CAr, OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having up to 40 C atoms optionally substituted by one or more radicals R 2 , a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced

by —R 2 C═CR 2 —, C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)R 2 , S═O, SO 2 , NR 2 , —O—, —S—, or —CONR 2 — and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R 2 , or a combination of two, three, four or five of these systems; and wherein two or more substituents R 1 , either on the same ring or on different rings, optionally define a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another; with the proviso that at least one radical R is not equal to hydrogen;

R 2 is, identically or differently on each occurrence, H or an aliphatic, aromatic, and/or heteroaromatic hydrocarbon radical having up to 20 C atoms, wherein two or more radicals R 2 optionally define a ring system with one another;

Ar is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5-30 aromatic ring atoms optionally substituted by one or more non-aromatic radicals R l ;

L is an at least divalent straight-chain alkylene, alkylidene, alkyleneoxy, or thioalkyleneoxy group having up to 40 C atoms optionally substituted by one or more radicals R 2 , or a branched or cyclic alkylene, alkylidene, alkyleneoxy or thioalkyleneoxy group having 3 to 40 C atoms optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by —CR 2 ═CR 2 —, —C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)R 2 , S═O, SO 2 , —O—, —S—, or —CONR 2 — and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN, or NO 2 , an at least divalent aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , P(R 1 ) 3-p , P(═O)(R 1 ) 3-p C(R 1 ) 4-p , Si(R 1 ) 4-p , N(Ar) 3-p , or a combination of two, three, four or five of these systems; or is a chemical bond;

n is, identically or differently on each occurrence, 0, 1, or 2, wherein when n =0, a hydrogen or R 1 is present instead of Y, with the proviso that at least two n are not equal to 0;

p is 2, 3, 4, 5, or 6, with the proviso that p is not greater than the maximum valency of L.

11. The compound of claim 10 , wherein X is nitrogen, phosphorus, or P═O.

12. The compound of claim 10 , wherein Y is, identically or differently on each occurrence, O, S, C(R 1 ) 2 , C═O, P(═O)R 1 , C═C(R 1 ) 2 , NR 1 , SO, SO 2 , or a chemical bond.

13. The compound of claim 10 , wherein R l is, identically or differently on each occurrence, H, CF 3 , OCH 3 , OCF 3 , an aliphatic, aromatic, or heteroaromatic hydrocarbon radical having up to 10 C atoms, or in that R 1 on bridges Y stands for an aliphatic hydrocarbon radical having up to 6 C atoms or for an aryl or heteroaryl group having 6 to 10 C atoms, wherein two radicals R 1 on the same bridge Y optionally define a ring system with one another.

14. The compound of claim 10 , wherein R is, identically or differently on each occurrence, CR 2 ═CR 2 Ar, C≡CAr, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, optionally substituted by one or more non-aromatic radicals R 2 .

15. The compound of claim 10 , wherein L is —CR 2 ═CR 2 —, —C≡C—, C═O, S═O, SO 2 , —O—, —S—, P(R 1 ) 3-p , P(═O)(R 1 ) 3-p , C(R 1 ) 4-p , Si(R 1 ) 4-p , N(Ar) 3-p , or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, optionally substituted by one or more radicals R 2 , or a combination of two, three or four of these systems or a chemical bond.

16. A polymer, oligomer, or dendrimer comprising one or more compounds of formula (1) and/or formula (2)

wherein

X is, identically or differently on each occurrence, N, P, As, Sb, P═O, As═O, or Sb═O;

Y is, identically or differently on each occurrence, O, S, C(R 1 ) 2 , C═O, C═S, C═NR 1 , C═C(R 1 ) 2 , Si(R 1 ) 2 , BR 1 ,NR 1 , PR 1 , AsR 1 , SbR 1 , BiR 1 , P(═O)R 1 , As(═O)R 1 , Sb(═O)R 1 , Bi(═O)R 1 , SO, SeO, TeO, SO 2 , SeO 2 , TeO 2 , or a chemical bond;

R 1 is, identically or differently on each occurrence, H, OH, F, Cl, Br, I, CN, CHO, NO 2 , N(Ar) 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)Ar, P(═O)Ar 2 , S(═O)Ar, S(═O)Ar 2 , CR 2 ═CR 2 Ar, C≡CAr, OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having up to 40 C atoms optionally substituted by one or more radicals R 2 , a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by —R 2 C═CR 2 —, C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)R 2 , S═O, SO 2 , NR 2 , —O—, —S—, or —CONR 2 — and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R 2 , or a combination of two, three, four or five of these systems; and wherein two or more substituents R 1 , either on the same ring or on different rings, optionally define a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another, or is a bond;

R is, identically or differently on each occurrence in the compound of formula (1), H, CHO, B(OR 2 ) 2 , P(R 2 ) 2 , CR 2 ═CR 2 Ar, C≡CAr, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, optionally substituted by one or more non-aromatic radicals R 1 , or a combination of two, three, four or five of these radicals, or is a bond,

and

is, identically or differently on each occurrence in the compound of formula (2), H, OH, F, Cl, Br, I, CN, CHO, NO 2 , N(Ar) 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)Ar, P(═O)Ar 2 , S(═O)Ar, S(═O)Ar 2 , CR 2 ═CR 2 Ar, C≡CAr, OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having up to 40 C atoms optionally substituted by one or more radicals R 2 , a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by —R 2 C═CR 2 —, C≡C-, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)R 2 , S═O, SO 2 , NR 2 , —O—, —S—, or —CONR 2 — and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R 2 , or a combination of two, three, four or five of these systems; and wherein two or more substituents R′, either on the same ring or on different rings, optionally define a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another; with the proviso that at least one radical R is not equal to hydrogen, or is a bond;

R 2 is, identically or differently on each occurrence, H or an aliphatic, aromatic, and/or heteroaromatic hydrocarbon radical having up to 20 C atoms, wherein two or more radicals R 2 optionally define a ring system with one another;

Ar is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5-30 aromatic ring atoms optionally substituted by one or more non-aromatic radicals R 1 ;

L is an at least divalent straight-chain alkylene, alkylidene, alkyleneoxy, or thioalkyleneoxy group having up to 40 C atoms optionally substituted by one or more radicals R 2 , or a branched or cyclic alkylene, alkylidene, alkyleneoxy or thioalkyleneoxy group having 3 to 40 C atoms optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by —CR 2 ═CR 2 —, —C≡C-, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)R 2 , S═0, SO 2 , —O—, —S—, or —CONR 2 — and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN, or NO 2 , an at least divalent aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , P(R 1 ) 3-p , P(═O)(R 1 ) 3-p , C(R 1 ) 4-p , Si(R 1 ) 4-p , N(Ar) 3-p , or a combination of two, three, four or five of these systems; or is a chemical bond;

n is, identically or differently on each occurrence, 0, 1, or 2, wherein when n =0, a hydrogen or R 1 is present instead of Y, with the proviso that at least two n are not equal to 0;

p is 2, 3, 4, 5, or 6, with the proviso that p is not greater than the maximum valency of L,

as recurring units, wherein at least one R or R 1 of said one or more compounds of formula (1) and/or formula (2) is a bond to said polymer, oligomer, or dendrimer.

17. A process for preparing compounds of claim 10 , comprising functionalizing the unfuntionalized parent structure of formula (1) wherein all the radicals R are hydrogen is functionalized and introducing substituents R onto the functionalized parent structure of formula (1).

18. The process of claim 17 , wherein said functionalizing is achieved by brominating said unfuntionalized parent structure of formula (1).

19. The organic electroluminescent device of claim 8 , wherein said at least one compound of formula (1) and/or compound of formula (2) is present in said at least one emitting layer as a dopant material in combination with a host material.

20. The organic electroluminescent device of claim 19 , wherein said host material is selected from the group consisting of oligoarylenes containing naphthalene, anthracene, pyrene, mixtures thereof, and atropisomers thereof, oligoarylenevinylenes, ketones, phosphine oxides, and sulfoxides.

21. The organic electroluminescent device of claim 8 , wherein said at least one compound of formula (1) and/or compound of formula (2) is present in said at least one emitting layer as a host material in combination with a dopant material.

22. The organic electroluminescent device of claim 21 , wherein said at least one compound of formula (1) and/or compound of formula (2) is present in said emitting layer in a concentration of 80 to 99.5% by weight.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 12, 2008
From: PARHAM, AMIR; HEUN, SUSANNE; VESTWEBER, HORST; STOESSEL, PHILIPP; HEIL, HOLGER; FORTTE, ROCCO
To: MERCK PATENT GMBH
Reel/Frame 020640/0294 →
Priority Claims (1)
DE 10 2005 043 163 · Sep 12, 2005 · national
Continuity (1)
Related Publication 20090295275A1 · Dec 3, 2009