Electroluminescent Device

Abstract

Disclosed are electroluminescent devices that comprise organic layers that contain certain organic compounds containing one ore more pyrimidine moieties. The organic compounds containing one ore more pyrimidine moieties are suitable components of blue-emitting, durable, organo-electroluminescent layers. The electroluminescent devices may be employed for full color display panels in for example mobile phones, televisions and personal computer screens.

Claims

1-16. (canceled)

17. A compound of formula (I) ##STR00218## wherein V is C.sub.6-C.sub.30aryl or C.sub.2-C.sub.30heteroaryl, which can be substituted or unsubstituted, H, C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkenyl, C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D; —SR.sup.5; —NR.sup.5R.sup.6; W is C.sub.6-C.sub.30aryl or C.sub.2-C.sub.30heteroaryl, which can be substituted or unsubstituted, H C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkenyl, C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D: C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D; —SR.sup.5; —NR.sup.5R.sup.6; Y is C.sub.6-C.sub.30aryl or C.sub.2-C.sub.30heteroaryl, which can be substituted or unsubstituted, H, C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkenyl, C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D; —SR.sup.5; —NR.sup.5R.sup.6; X is C.sub.6-C.sub.30aryl or C.sub.2-C.sub.30heteroaryl, which can be substituted or unsubstituted, H, C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkenyl, C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D; —SR.sup.5; —NR.sup.5R.sup.6; or one or more of the substituents V, W, X, or Y is a group of the formula —Z or —Ar—Z, wherein Ar is ##STR00219## wherein Z is a group of formula ##STR00220## wherein A.sup.1, B.sup.1 and B.sup.2 are independently of each other H; C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by G; C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.7-C.sub.18alkylaryl; C.sub.7-C.sub.18alkylaryl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkenyl; C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy, C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D; —SR.sup.5; —NR.sup.5R.sup.6; C.sub.2-C.sub.18heteroaryl; C.sub.2-C.sub.18heteroaryl which is substituted by L; —SOR.sup.4; —SO.sub.2R.sup.4; —COR.sup.8; —COOR.sup.7; —CONR.sup.5R.sup.6; C.sub.4-C.sub.18cycloalkyl; C.sub.4-C.sub.18cycloalkyl which is optionally substituted by E and optionally interrupted by D; C.sub.4-C.sub.18cycloalkenyl; C.sub.4-C.sub.18cycloalkenyl which is optionally substituted by E and optionally interrupted by D; wherein two substituents A.sup.1, B.sup.1, B.sup.2 or B.sup.1 and B.sup.2 optionally form a five to seven membered ring, which is optionally substituted, m is an integer of 1 to 4; D is —CO—; —COO—; —OCOO—; —S—; —SO—; —SO.sub.2—; —O—; —NR.sup.5—; —SiR.sup.5R.sup.6—; —POR.sup.5—; —CR.sup.5═CR.sup.6—; or —C≡C—; E is —OR.sup.5; —SR.sup.5; —NR.sup.5R.sup.6; —COR.sup.8; —COOR.sup.7; —CONR.sup.5R.sup.6; —CN; —OCOOR.sup.7; or halogen; G is E; K; heteroaryl; heteroaryl which is substituted by C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by E and/or K; K is C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.7-C.sub.18alkylaryl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkenyl; C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy, C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D; C.sub.4-C.sub.18cycloalkyl; C.sub.4-C.sub.18cycloalkyl which is optionally substituted by E and optionally interrupted by D; C.sub.4-C.sub.18cycloalkenyl; or C.sub.4-C.sub.18cycloalkenyl which is optionally substituted by E and optionally interrupted by D; L is E; K; C.sub.6-C.sub.18aryl; or C.sub.6-C.sub.18aryl which is substituted by G, E and/or K; R.sup.4 is C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by C.sub.1-C.sub.18alkyl, C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkyl; or C.sub.1-C.sub.18alkyl which is interrupted by —O—; R.sup.5 and R.sup.6 are independently of each other H; C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by C.sub.1-C.sub.18alkyl, C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkyl; or C.sub.1-C.sub.18alkyl which is interrupted by —O—; wherein R.sup.5 and R.sup.6 optionally together form a five or six membered ring R.sup.7 is H; C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by C.sub.1-C.sub.18alkyl, C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is interrupted by —O—; R.sup.8 is H; C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by C.sub.1-C.sub.18alkyl, C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is interrupted by —O—; with the proviso that at least one of the groups V, W, X and Y is a C.sub.6-C.sub.24aryl, or C.sub.2-C.sub.24heteroaryl group, which is optionally substituted.

18. The compound of claim 17, wherein W, X, and Y are each C.sub.6-C.sub.30aryl or C.sub.2-C.sub.30heteroaryl; at least one of the groups W, X, and Y is represented by ##STR00221## wherein R.sup.11, R.sup.11′, R.sup.12, R.sup.12′, R.sup.13, R.sup.13′, R.sup.15, R.sup.15′, R.sup.16, R.sup.16′, R.sup.17, and R.sup.17′ are independently of each other H, E, C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by E; C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.7-C.sub.18aralkyl; or C.sub.7-C.sub.18aralkyl which is substituted by E; the substituent pairs R.sup.11′ and R.sup.12, R.sup.12′ and R.sup.13, R.sup.15′ and R.sup.16, and R.sup.16′ and R.sup.17 are each optionally a divalent group selected from an oxygen atom, an sulfur atom, >CR.sup.118R.sup.119, >SiR.sup.118R.sup.119, and ##STR00222## wherein R.sup.118 and R.sup.119 are independently of each other C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkoxy, C.sub.6-C.sub.18aryl; C.sub.7-C.sub.18aralkyl; R.sup.49 and R.sup.50 are independently of each other H, C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl, which is optionally substituted by E and optionally interrupted by D; E; C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl, which is substituted by E; and the substituent pairs R.sup.11 and R.sup.11′, R.sup.12 and R.sup.12′, R.sup.13 and R.sup.13′, R.sup.13′ and R.sup.14, R.sup.14 and R.sup.15, R.sup.15 and R.sup.15′, R.sup.16 and R.sup.16′, and R.sup.17′ and R.sup.17, are each optionally the divalent group ##STR00223## wherein R.sup.30, R.sup.31, R.sup.32, and R.sup.33 are independently of each other H, C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl, which is optionally substituted by E and optionally interrupted by D; E; C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl, which is substituted by E; R.sup.14 is H, C.sub.2-C.sub.30heteroaryl, C.sub.6-C.sub.30aryl, or C.sub.6-C.sub.30aryl which is substituted by E, C.sub.1-C.sub.18alkyl; or C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; D is —CO—; —COO—; —OCOO—; —S—; —SO—; —SO.sub.2—; —O—; —NR.sup.5—; SiR.sup.5R.sup.6—; —POR.sup.5—; —CR.sup.9═CR.sup.10—; or —C≡C—; E is —OR.sup.5; —SR.sup.5; —NR.sup.5R.sup.6; —COR.sup.8; —COOR.sup.7; —CONR.sup.5R.sup.6; —CN; or halogen, especially F, or Cl; wherein R.sup.5 and R.sup.6 are independently of each other C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by C.sub.1-C.sub.18alkyl, C.sub.1-C.sub.18alkyl; or C.sub.6-C.sub.18alkyl which is interrupted by —O—; wherein R.sup.5 and R.sup.6 together optionally form a five or six membered ring, R.sup.7 is C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by C.sub.1-C.sub.18alkyl, C.sub.1-C.sub.18alkyl; or C.sub.1-C.sub.18alkyl which is interrupted by —O—; R.sup.8 is C.sub.7-C.sub.12alkylaryl; C.sub.1-C.sub.18alkyl; or C.sub.1-C.sub.18alkyl which is interrupted by —O—; and R.sup.9 and R.sup.10 are independently of each other H, C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by C.sub.1-C.sub.18alkyl, C.sub.1-C.sub.18alkyl; or C.sub.1-C.sub.18alkyl which is interrupted by —O—.

19. The compound of claim 17, wherein W and Y are independently ##STR00224##

20. The compound of claim 17, wherein V is H; W and Y are independently ##STR00225## and X is ##STR00226##

21. The compound of claim 17, wherein V is ##STR00227## C.sub.2-C.sub.30heteroaryl, H, C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkenyl, C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D: —SR.sup.5; or —NR.sup.5R.sup.6; X is ##STR00228## C.sub.2-C.sub.30heteroaryl, H, C.sub.2-C.sub.30heteroaryl, C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkenyl, C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D; —SR.sup.5; or —NR.sup.5R.sup.6 W is ##STR00229## Y is ##STR00230## C.sub.2-C.sub.30heteroaryl, H, C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkenyl, C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D: —SR.sup.5; or —NR.sup.5R.sup.6; wherein the groups V.sup.1 to V.sup.5, W.sup.1 to W.sup.5, X.sup.1 to X.sup.5 and Y.sup.1 to Y.sup.5 are each independently H; halogen, C.sub.6-C.sub.24aryl; C.sub.6-C.sub.24aryl which is substituted by G; C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.7-C.sub.18alkylaryl; C.sub.7-C.sub.18alkylaryl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkenyl; C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D; ##STR00231## wherein Ar.sup.1 is C.sub.6-C.sub.30aryl or C.sub.2-C.sub.30heteroaryl, especially phenyl, Ar.sup.2 is C.sub.6-C.sub.30aryl or C.sub.2-C.sub.30heteroaryl, especially phenyl, or H, C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy, C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D; —SR.sup.5; —NR.sup.5R.sup.6; C.sub.2-C.sub.24heteroaryl; C.sub.2-C.sub.24heteroaryl which is substituted by L; —SOR.sup.4; —SO.sub.2R.sup.4; —COR.sup.8; —COOR.sup.7; —CONR.sup.5R.sup.6; C.sub.4-C.sub.18cycloalkyl; C.sub.4-C.sub.18cycloalkyl which is optionally substituted by E and optionally interrupted by D; C.sub.4-C.sub.18cycloalkenyl; C.sub.4-C.sub.18cycloalkenyl which is optionally substituted by E and optionally interrupted by D; or W.sup.5 or Y.sup.5 together with V form a group —CR.sup.9.sub.2—, —CR.sup.9.sub.2—CR.sup.9.sub.2—, —C(═O)CR.sup.9.sub.2—, —C(═O)—, or —CR.sup.9═CR.sup.9—, or W.sup.5 and Y.sup.5 together with V form a group ##STR00232## wherein R.sup.9 is H; C.sub.1-C.sub.18alkyl, C.sub.1-C.sub.18alkyl which is interrupted by —O—, C.sub.6-C.sub.18aryl, C.sub.6-C.sub.18aryl which is substituted by C.sub.1-C.sub.18alkyl, or C.sub.1-C.sub.18alkoxy, or one or more of the substituents V.sup.1 to V.sup.5, W.sup.1 to W.sup.5, X.sup.1 to X.sup.5, or Y.sup.1 to Y.sup.5 is a group of the formula —Z′ or —Ar—Z′, wherein Ar is ##STR00233## wherein Z′ is a group of formula ##STR00234## wherein two adjacent substituents V.sup.1 to V.sup.5, W.sup.1 to W.sup.5, X.sup.1 to X.sup.5, or Y.sup.1 to Y.sup.5 optionally join to form a five to seven membered ring.

22. The compound of claim 21, wherein W is ##STR00235## X is ##STR00236## and Y is ##STR00237##

23. The compound of claim 21, wherein the compound is represented by formula (IV) ##STR00238## wherein V is H or C.sub.1-C.sub.18 alkyl; W.sup.1, W.sup.5, Y.sup.1, Y.sup.5, X.sup.1, and X.sup.5 are independently of each other H; C.sub.1-C.sub.18alkyl; or C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; and W.sup.3, X.sup.3 and Y.sup.3 are selected from the group consisting of C.sub.6-C.sub.24aryl, C.sub.6-C.sub.24aryl which is substituted by G, C.sub.2-C.sub.24heteroaryl, C.sub.2-C.sub.24heteroaryl which is substituted by L, C.sub.1-C.sub.18alkoxy, —SR.sup.5, and —NR.sup.5R.sup.6.

24. The compound of claim 21, wherein the compound is represented by formula (Xa) or (Xb) ##STR00239## wherein V is H or C.sub.1-C.sub.8alkyl; X.sup.3 and X.sup.4 are independently of each other H, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8thioalkyl, or phenyl, X.sup.5 is H or C.sub.1-C.sub.8alkoxy; W.sup.5 is H, C.sub.1-C.sub.8alkyl, or O(CH.sub.2).sub.n1—X; Y.sup.5 is H, C.sub.1-C.sub.8alkyl, or O(CH.sub.2).sub.n1—X; Y.sup.3, Y.sup.4, W.sup.3, and W.sup.4 are independently of each other C.sub.1-C.sub.8alkyl; C.sub.1-C.sub.8alkoxy; C.sub.1-C.sub.8thioalkyl; halogen; phenyl; or O(CH.sub.2).sub.n1—X; each occurrence of n1 is independently an integer of 1 to 5; each X is independently —O—(CH.sub.2).sub.m1CH.sub.3, —OC(O)—(CH.sub.2).sub.m1CH.sub.3, —C(O)—O—C.sub.1-C.sub.8alkyl, or —NR.sup.103R.sup.104; wherein m1 is an integer of 0 to 5; and R.sup.103 and R.sup.104 are independently of each other H or C.sub.1-C.sub.8-alkyl, wherein R.sup.103 and R.sup.104together optionally form a five or six membered heterocyclic ring.

25. The compound of claim 21, wherein the compound is represented by formula (XI) ##STR00240## wherein V is H, or C.sub.1-C.sub.8alkyl; W.sup.3 is H, C.sub.1-C.sub.8alkyl, or C.sub.1-C.sub.8alkoxy; X.sup.3 is H, C.sub.1-C.sub.8alkoxy, phenyl or O(CH.sub.2).sub.n1—X; X.sup.5 is H, C.sub.1-C.sub.8alkoxy, phenyl or O(CH.sub.2).sub.n1—X; Y.sup.3 is H, C.sub.1-C.sub.8alkyl, or C.sub.1-C.sub.8alkoxy; each occurrence of n1 is independently an integer of 1 to 5; each X is independently —O—(CH.sub.2).sub.m1CH.sub.3, —OC(O)—(CH.sub.2).sub.m1CH.sub.3, —C(O)—O—C.sub.1-C.sub.8alkyl, or —NR.sup.103R.sup.104; wherein m1 is an integer of 0 to 5; and R.sup.103 and R.sup.104 are independently of each other H or C.sub.1-C.sub.8-alkyl, wherein R.sup.103 and R.sup.104 together optionally form a five or six membered heterocyclic ring.

26. The compound of claim 21, wherein the compound is represented by formula (XIVa), (XIVb), (XIVc), (XIVd), or (XIVe): ##STR00241## wherein each R.sup.9 is independently H; C.sub.1-C.sub.18alkyl, C.sub.1-C.sub.18alkyl which is interrupted by —O—, C.sub.6-C.sub.18aryl, C.sub.6-C.sub.18aryl which is substituted by C.sub.1-C.sub.18alkyl, or C.sub.1-C.sub.18alkoxy.

27. The compound of claim 21, wherein the compound is represented by formula (XVIII) ##STR00242## wherein W.sup.3 and Y.sup.3 are a group of formula ##STR00243## wherein each occurrence of R.sup.110 is C.sub.4-C.sub.10-heteroaryl, phenyl, 1-naphthyl, 2-naphthyl, 3-biphenyl, 4-biphenyl, 9-phenanthryl, 2-fluorenyl, or 9-fluorenyl; each of which is optionally substituted by C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.4-alkoxy; and X.sup.3 is H, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.4-alkoxy, phenyl, or ##STR00244##

28. The compound of 21, wherein the compound is represented by one of compound A-1 to A-52: ##STR00245## TABLE-US-00011 Cpd. X.sup.3 Y.sup.3 W.sup.3 X.sup.5 Y.sup.1 W.sup.5 V A-1 H OCH.sub.2COOMe OCH.sub.2COOMe H OCH.sub.2COOMe OCH.sub.2COOMe H A-2 Ph OCH.sub.2COOMe OCH.sub.2COOMe H OCH.sub.2COOMe OCH.sub.2COOMe H A-3 H OMe OMe H H H H A-4 H Ph Ph H H H H A-5 H OMe OMe H OMe OMe H A-6 H OBu OBu H H H H A-7 H OBu OBu H OBu OBu H A-8 OMe OMe OMe OMe OMe OMe H A-9 OMe Br Br OMe H H H A-10 Ph Br Br H H H H A-11 OMe Ph Ph OMe H H H A-12 Ph Ph Ph H H H H A-13 SMe SMe SMe H H H H A-14 H SMe SMe H H H H A-15 H OCH.sub.2CH.sub.2OAc OCH.sub.2CH.sub.2OAc H H H H A-16 H OCH.sub.2CH.sub.2OAc OCH.sub.2CH.sub.2OAc H OCH.sub.2CH.sub.2OAc OCH.sub.2CH.sub.2OAc H A-17 H OCH.sub.2CH.sub.2OCH.sub.2Et OCH.sub.2CH.sub.2OCH.sub.2Et H H H H A-18 H OCH.sub.2CH.sub.2OCH.sub.2Et OCH.sub.2CH.sub.2OCH.sub.2Et H OCH.sub.2CH.sub.2OCH.sub.2Et OCH.sub.2CH.sub.2OCH.sub.2Et H A-19 H N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 H H H H A-20 H H H H H A-21 Ph N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 H H H H A-22 Ph H H H H A-23 H CH.sub.3 CH.sub.3 H H H H A-24 Ph CH.sub.3 CH.sub.3 H H H H A-25 Ph Ph Ph H H H CH.sub.3 A-26 OMe OMe OMe H H H CH.sub.3 A-27 H Ph Ph H H H CH.sub.3 A-28 H OMe OMe H H H CH.sub.3 A-29 H OMe OMe H OMe OMe CH.sub.3 A-30 H OBu OBu H H H CH.sub.3 A-31 H OBu OBu H OBu OBu CH.sub.3 A-32 OMe OMe OMe OMe OMe OMe CH.sub.3 A-33 OMe Br Br OMe H H CH.sub.3 A-34 Ph Br Br H H H CH.sub.3 A-35 OMe Ph Ph. OMe H H CH.sub.3 A-36 H OCH.sub.2COOMe OCH.sub.2COOMe H OCH.sub.2COOMe OCH.sub.2COOMe CH.sub.3 A-37 SMe SMe SMe H H H CH.sub.3 A-38 H SMe SMe H H H CH.sub.3 A-39 H OCH.sub.2CH.sub.2OAc OCH.sub.2CH.sub.2OAc H H H CH.sub.3 A-40 H OCH.sub.2CH.sub.2OAc OCH.sub.2CH.sub.2OAc H OCH.sub.2CH.sub.2OAc OCH.sub.2CH.sub.2OAc CH.sub.3 A-41 H OCH.sub.2CH.sub.2OCH.sub.2Et OCH.sub.2CH.sub.2OCH.sub.2Et H H H CH.sub.3 A-42 H OCH.sub.2CH.sub.2OCH.sub.2Et OCH.sub.2CH.sub.2OCH.sub.2Et H OCH.sub.2CH.sub.2OCH.sub.2Et OCH.sub.2CH.sub.2OCH.sub.2Et CH.sub.3 A-43 OBu Ph Ph OBu H H CH.sub.3 A-44 H N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 H H H CH.sub.3 A-45 H H H H CH.sub.3 A-46 Ph N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 H H H CH.sub.3 A-47 Ph H H H CH.sub.3 A-48 Ph CH.sub.3 CH.sub.3 H H H CH.sub.3 A-49 Ph CH.sub.3 CH.sub.3 H H H CH.sub.3 A-50 OMe OMe OMe H H H H A-51 H H H H H H H A-52 Ph H H H H H H.

29. The compound of claim 21, wherein the compound is represented by one of compound B-1 to B-23: ##STR00254## TABLE-US-00012 Cpd. X.sup.3 V.sup.3 W.sup.3 X.sup.5 V B-1 Ph H H H H B-2 H H H H H B-3 OBu H H OBu H B-4 OMe H H OMe H B-5 OCH.sub.2COOMe H H OCH.sub.2COOMe H B-6 H OMe OMe H H B-7 OCH.sub.2CH.sub.2OCH.sub.2Et H H OCH.sub.2CH.sub.2OCH.sub.2Et H B-8 OCH.sub.2CH.sub.2OAc H H OCH.sub.2CH.sub.2OAc H B-9 OMe OMe OMe OMe H B-10 OMe OMe OMe OMe H B-11 H CH.sub.3 CH.sub.3 H H B-12 Ph CH.sub.3 CH.sub.3 H H B-13 Ph H H H CH.sub.3 B-14 OMe H H OMe CH.sub.3 B-15 OBu H H OBu CH.sub.3 B-16 H H H H CH.sub.3 B-17 OCH.sub.2COOMe H H OCH.sub.2COOMe CH.sub.3 B-18 H OMe OMe H CH.sub.3 B-19 OCH.sub.2CH.sub.2OCH.sub.2Et H H OCH.sub.2CH.sub.2OCH.sub.2Et CH.sub.3 B-20 OCH.sub.2CH.sub.2OAc H H OCH.sub.2CH.sub.2OAc CH.sub.3 B-21 H CH.sub.3 CH.sub.3 H CH.sub.3 B-22 Ph CH.sub.3 CH.sub.3 H CH.sub.3.

30. The compound of 21, wherein the compound is represented by one of the following compounds: ##STR00255## ##STR00256## ##STR00257## ##STR00258##

31. The compound of claim 21, wherein the compound is represented by one of compound K-1 to K-16: ##STR00259## TABLE-US-00013 Cpd. Ar Cpd. Ar K-1 K-2 K-3 K-4 K-5 K-6 K-7 K-8 K-9 K-10 K-11 K-12 K-13 K-14 K-15 K-16

32. The compound of claim 17, wherein the compound is represented by formula (III) ##STR00276## wherein X and Y are each independently selected from the group consisting of C.sub.6-C.sub.30aryl or C.sub.2-C.sub.30heteroaryl which can be substituted or unsubstituted, H, C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkenyl, C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D; —SR.sup.5; and —NR.sup.5R.sup.6; if X is ##STR00277## then Y is R.sup.1, or if Y is ##STR00278## then X is R.sup.1; R.sup.1 is H; C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.8alkenyl; C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D; —SR.sup.5; or —NR.sup.5R.sup.6; V is H, C.sub.6-C.sub.30aryl or C.sub.2-C.sub.30heteroaryl, which can be substituted or unsubstituted; C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkenyl, C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D: C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D; —SR.sup.5; or —NR.sup.5R.sup.6; W.sup.1 to W.sup.5, X.sup.1 to X.sup.5 and Y.sup.1 to Y.sup.5 are independently of each other H; C.sub.6-C.sub.24aryl; C.sub.6-C.sub.24aryl which is substituted by G; C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.7-C.sub.18alkylaryl; C.sub.7-C.sub.18alkylaryl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkenyl; C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D; ##STR00279## wherein Ar.sup.1 is C.sub.6-C.sub.30aryl or C.sub.2-C.sub.30heteroaryl and Ar.sup.2 is C.sub.6-C.sub.30aryl or C.sub.2-C.sub.30heteroaryl; C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D; —SR.sup.5; —NR.sup.5R.sup.6; C.sub.2-C.sub.24heteroaryl; C.sub.2-C.sub.24heteroaryl which is substituted by L; —SOR.sup.4; —SO.sub.2R.sup.4; —COR.sup.8; —COOR.sup.7; —CONR.sup.5R.sup.6; C.sub.4-C.sub.18cycloalkyl; C.sub.4-C.sub.18cycloalkyl which is optionally substituted by E and optionally interrupted by D; C.sub.4-C.sub.18cycloalkenyl; or C.sub.4-C.sub.18cycloalkenyl which is optionally substituted by E and optionally interrupted by D; wherein two adjacent substituents selected from V, W.sup.1 to W.sup.5, X.sup.1 to X.sup.5, and Y.sup.1 to Y.sup.5 optionally join to form a five to seven membered ring; D is —CO—; —COO—; —OCOO—; —S—; —SO—; —SO.sub.2—; —O—, —NR.sup.5—; —SiR.sup.5R.sup.6—; —POR.sup.5—; —CR.sup.5═CR.sup.6— or —C≡C—; E is —OR.sup.5; —SR.sup.5; —NR.sup.5R.sup.6; —COR.sup.8; —COOK′; —CONR.sup.5R.sup.6; —CN; —OCOOR.sup.7 or halogen; G is E; K; heteroaryl; heteroaryl which is substituted by C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by E or K; K is C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is optionally substituted by E and optionally interrupted by D; C.sub.7-C.sub.18alkylaryl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkenyl; C.sub.2-C.sub.18alkenyl which is optionally substituted by E and optionally interrupted by D; C.sub.2-C.sub.18alkynyl; C.sub.2-C.sub.18alkynyl which is optionally substituted by E and optionally interrupted by D; C.sub.1-C.sub.18alkoxy, C.sub.1-C.sub.18alkoxy which is optionally substituted by E and optionally interrupted by D; C.sub.4-C.sub.18cycloalkyl; C.sub.4-C.sub.18cycloalkyl which is optionally substituted by E and optionally interrupted by D; C.sub.4-C.sub.18cycloalkenyl; or C.sub.4-C.sub.18cycloalkenyl which is optionally substituted by E and optionally interrupted by D; L is E; K; C.sub.6-C.sub.18aryl or C.sub.6-C.sub.18aryl which is substituted by G, E or K; R.sup.4 is C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by C.sub.1-C.sub.18alkyl or C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkyl; or C.sub.1-C.sub.18alkyl which is interrupted by —O—; R.sup.5 and R.sup.6 are independently of each other H; C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by C.sub.1-C.sub.18alkyl or C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkyl; or C.sub.1-C.sub.18alkyl which is interrupted by —O—; or R.sup.5 and R.sup.6 together form a five or six membered ring; R.sup.7 is H; C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by C.sub.1-C.sub.18alkyl or C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is interrupted by —O—; R.sup.8 is H; C.sub.6-C.sub.18aryl; C.sub.6-C.sub.18aryl which is substituted by C.sub.1-C.sub.18alkyl or C.sub.1-C.sub.18alkoxy; C.sub.1-C.sub.18alkyl; C.sub.1-C.sub.18alkyl which is interrupted by —O—.

33. An electroluminescent device comprising the compound of claim 17.

34. An electroluminescent device comprising the compound of claim 21.

35. An electroluminescent device comprising the compound of claim 22.

36. An electroluminescent device comprising the compound of claim 32.

Description

EXAMPLES

Example 1 (A-1)

[0106] ##STR00105##

[0107] To 1.00 g (2.69 mmol) of educt 1 (prepared according to U.S. Pat. No. 3,442,898 from resorcinol and 4,6-dichloro-2-phenyl-pyrimidine; J. Org. Chem. 1988, 53, 4137) in 20 ml water free DMF 3.29 g (21.5 mmol) methyl-bromoacetate and 2.97 g (21.5 mmol) potassium carbonate are added. The reaction mixture is stirred at 100° C. under nitrogen for 2 h. The reaction mixture is diluted with water. The organic phase is extracted with dichloromethane und dried with magnesium sulfate. The solvent is removed. After chromatography of the crude product on silica gel with toluene/ethyl acetate 8/2 the desired product is obtained. Melting point: 178.0-179.0° C.

Example 2 (A-2)

[0108] ##STR00106##

[0109] To 520 mg (1.16 mmol) of educt 2 (prepared according to U.S. Pat. No. 3,442,898 from resorcinol and 4,6-dichloro-2-biphenyl-pyrimidine; EP-A-96657) in 20 ml water free DMF 1.42 g (9.28 mmol) methyl-bromoacetate and 1.28 g (9.28 mmol) potassium carbonate are added. The reaction mixture is stirred at 100° C. under nitrogen for 2 h. The reaction mixture is diluted with water. The organic phase is extracted with dichloromethane und dried with magnesium sulfate. The solvent is removed. After chromatography of the crude product on silica gel with toluene/ethyl acetate 9/1 and later 7/3 the desired product is obtained. Melting point: 119.5-121.5° C.

Example 3 (A-3)

[0110] ##STR00107##

[0111] To 4.31 g (16.1 mmol) of 1,3-bis(4-methoxyphenyl)-2-propen-1-one in 25 ml water free ethanol 1.89 g (8.11 mmol) biphenylbenzamidine hydrochlorid are added. A solution of 1.07 g (19.08 mmol) potassium hydroxide is added during 15 min. Dry air is bubbled through the reaction mixture. The reaction mixture is refluxed for 24 h. The reaction mixture is poured into water. The solid is filtered off and washed with water. The product is crystallized 2 times from acetic acid (96-98%). Melting point: 168-169° C.

[0112] Compounds A-4 to A-54 can be obtained in a manner analogous to Examples 1 to 5.

##STR00108##

(A-54; melting point: 162-164° C.)

TABLE-US-00001 Cpd. X.sup.3 Y.sup.3 W.sup.3 X.sup.5 Y.sup.1 W.sup.5 V A-1 H OCH.sub.2COOMe OCH.sub.2COOMe H OCH.sub.2COOMe OCH.sub.2COOMe H A-2 Ph OCH.sub.2COOMe OCH.sub.2COOMe H OCH.sub.2COOMe OCH.sub.2COOMe H A-3 H OMe OMe H H H H A-4.sup.1) H Ph Ph H H H H A-5 H OMe OMe H OMe OMe H A-6 H OBu OBu H H H H A-7 H OBu OBu H OBu OBu H A-8 OMe OMe OMe OMe OMe OMe H A-9 OMe Br Br OMe H H H A-10 Ph Br Br H H H H A-11 OMe Ph Ph OMe H H H A-12 Ph Ph Ph H H H H A-13 SMe SMe SMe H H H H A-14 H SMe SMe H H H H A-15 H OCH.sub.2CH.sub.2OAc OCH.sub.2CH.sub.2OAc H H H H A-16 H OCH.sub.2CH.sub.2OAc OCH.sub.2CH.sub.2OAc H OCH.sub.2CH.sub.2OAc OCH.sub.2CH.sub.2OAc H A-17 H OCH.sub.2CH.sub.2OCH.sub.2Et OCH.sub.2CH.sub.2OCH.sub.2Et H H H H A-18 H OCH.sub.2CH.sub.2OCH.sub.2Et OCH.sub.2CH.sub.2OCH.sub.2Et H OCH.sub.2CH.sub.2OCH.sub.2Et OCH.sub.2CH.sub.2OCH.sub.2Et H A-19 H N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 H H H H A-20 H [00109] [00110] H H H H A-21 Ph N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 H H H H A-22 Ph [00111] [00112] H H H H A-23 H CH.sub.3 CH.sub.3 H H H H A-24 Ph CH.sub.3 CH.sub.3 H H H H A-25 Ph Ph Ph H H H CH.sub.3 A-26 OMe OMe OMe H H H CH.sub.3 A-27 H Ph Ph H H H CH.sub.3 .sup.1)melting point: 244-245° C.

TABLE-US-00002 Cpd. X.sup.3 Y.sup.3 W.sup.3 X.sup.5 Y.sup.1 W.sup.5 V A-28 H OMe OMe H H H CH.sub.3 A-29 H OMe OMe H OMe OMe CH.sub.3 A-30 H OBu OBu H H H CH.sub.3 A-31 H OBu OBu H OBu OBu CH.sub.3 A-32 OMe OMe OMe OMe OMe OMe CH.sub.3 A-33 OMe Br Br OMe H H CH.sub.3 A-34 Ph Br Br H H H CH.sub.3 A-35 OMe Ph Ph OMe H H CH.sub.3 A-36 H OCH.sub.2COOMe OCH.sub.2COOMe H OCH.sub.2COOMe OCH.sub.2COOMe CH.sub.3 A-37 SMe SMe SMe H H H CH.sub.3 A-38 H SMe SMe H H H CH.sub.3 A-39 H OCH.sub.2CH.sub.2Oac OCH.sub.2CH.sub.2Oac H H H CH.sub.3 A-40 H OCH.sub.2CH.sub.2Oac OCH.sub.2CH.sub.2Oac H OCH.sub.2CH.sub.2Oac OCH.sub.2CH.sub.2Oac CH.sub.3 A-41 H OCH.sub.2CH.sub.2OCH.sub.2Et OCH.sub.2CH.sub.2OCH.sub.2Et H H H CH.sub.3 A-42 H OCH.sub.2CH.sub.2OCH.sub.2Et OCH.sub.2CH.sub.2OCH.sub.2Et H OCH.sub.2CH.sub.2OCH.sub.2Et OCH.sub.2CH.sub.2OCH.sub.2Et CH.sub.3 A-43 OBu Ph Ph OBu H H CH.sub.3 A-44 H N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 H H H CH.sub.3 A-45 H [00113] [00114] H H H CH.sub.3 A-46 Ph N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 H H H CH.sub.3 A-47 Ph [00115] [00116] H H H CH.sub.3 A-48 Ph CH.sub.3 CH.sub.3 H H H CH.sub.3 A-49 Ph CH.sub.3 CH.sub.3 H H H CH.sub.3 A-50 OMe OMe OMe H H H H A-51.sup.1) H H H H H H H A-52.sup.2) Ph H H H H H H .sup.1)melting point: 188-189° C. .sup.2)melting point: 196-198° C.

Example 4 (B-1)

[0113] ##STR00117##

[0114] To 5.00 g (16.1 mmol) of 1,3-bis-α-naphthy-2-propen-1-one (1) in 25 ml water free ethanol 1.89 g (8.11 mmol) biphenylbenzamidine hydrochlorid are added. A solution of 1.07 g (19.08 mmol) potassium hydroxide in 25 ml water free ethanol is added during 15 min. Dry air was bubbled through the reaction mixture. The reaction mixture is refluxed for 24 h.

[0115] The reaction mixture is poured into water. The solid is filtered off and is washed with water.

[0116] The product is crystallized 2 times from acetic acid (96-98%). Melting point: 226-230° C.

Example 5 (B-2)

[0117] ##STR00118##

[0118] To 5.00 g (16.1 mmol) of 1,3-bis-α-naphthy-2-propen-1-one (1) in 25 ml water free ethanol 1.27 g (8.11 mmol) benzamidine hydrochlorid are added. A solution of 1.07 g (19.08 mmol) potassium hydroxide in 25 ml water free ethanol is added during 15 min. Dry air is bubbled through the reaction mixture. The reaction mixture is refluxed for 24 h. The reaction mixture is poured into water. The solid is filtered off and is washed with water. The product is crystallized from acetic acid (96-98%). Melting point: 179-180° C.

[0119] Compounds B-3 to B-23 can be obtained in a manner analogous to Examples 4 and 5.

##STR00119##

TABLE-US-00003 Cpd. X.sup.3 Y.sup.3 W.sup.3 X.sup.5 V B-1 Ph H H H H B-2 H H H H H B-3 OBu H H OBu H B-4 OMe H H OMe H B-5 OCH.sub.2COOMe H H OCH.sub.2COOMe H B-6 H OMe OMe H H B-7 OCH.sub.2CH.sub.2OCH.sub.2Et H H OCH.sub.2CH.sub.2OCH.sub.2Et H B-8 OCH.sub.2CH.sub.2OAc H H OCH.sub.2CH.sub.2OAc H B-9 OMe OMe OMe OMe H B-10 OMe OMe OMe OMe H B-11 H CH.sub.3 CH.sub.3 H H B-12 Ph CH.sub.3 CH.sub.3 H H B-13 Ph H H H CH.sub.3 B-14 OMe H H OMe CH.sub.3 B-15 OBu H H OBu CH.sub.3 B-16 H H H H CH.sub.3 B-17 OCH.sub.2COOMe H H OCH.sub.2COOMe CH.sub.3 B-18 H OMe OMe H CH.sub.3 B-19 OCH.sub.2CH.sub.2OCH.sub.2Et H H OCH.sub.2CH.sub.2OCH.sub.2Et CH.sub.3 B-20 OCH.sub.2CH.sub.2OAc H H OCH.sub.2CH.sub.2OAc CH.sub.3 B-21 H CH.sub.3 CH.sub.3 H CH.sub.3 B-22 Ph CH.sub.3 CH.sub.3 H CH.sub.3

Example 6 (C-1)

[0120] ##STR00120##

[0121] To 4.50 g (8.74 mmol) of the 2-propen-1-one derivative shown above in 50 ml water free ethanol 1.37 g (8.74 mmol) benzamidine hydrochloride are added. A solution of 1.15 g (20.6 mmol) potassium hydroxide in 50 ml water free ethanol is added during 15 min. Dry air is bubbled through the reaction mixture. The reaction mixture is refluxed for 24 h, poured into water and the water phase is extracted with dichloromethane. The organic phase is dried with magnesium sulfate, the solvent is removed by distillation and the remaining residue is purified by column chromatography (toluene/hexane 2/1).

[0122] .sup.1H-NMR (300 MHz, CDCl.sub.3): δ=8.75-8.72 (m, 4H); 8.45-8.37 (m, 12H); 8.04-7.82 (m, 6H); 7.67-7.50 (m, 12h).

[0123] Compounds C-2 to C-24 can be obtained in a manner analogous to Example 6.

##STR00121##

TABLE-US-00004 Cpd. W.sup.3 Y.sup.3 C-2 H H C-3 H H C-4 H H C-5 H H C-6 H H C-7 OCH.sub.3 OCH.sub.3 C-8 OCH.sub.3 OCH.sub.3 C-9 OCH.sub.3 OCH.sub.3 C-10 OCH.sub.3 OCH.sub.3 C-11 OCH.sub.3 OCH.sub.3 C-12 SCH.sub.3 SCH.sub.3 C-13 SCH.sub.3 SCH.sub.3 C-14 SCH.sub.3 SCH.sub.3 C-15 SCH.sub.3 SCH.sub.3 C-16 SCH.sub.3 SCH.sub.3 C-17 SCH.sub.3 SCH.sub.3 C-18 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 C-19 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 C-20 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 C-21 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 C-22 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 C-23 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 C-24 N(CH.sub.3).sub.2 N(CH.sub.3)2

[0124] Compounds D-1 to D-23 can be obtained in a manner analogous to Example 6.

##STR00122##

TABLE-US-00005 Cpd. R.sup.101 R.sup.102 W.sup.3 Y.sup.3 D-1 C.sub.6H.sub.13 C.sub.6H.sub.13 H H D-2 Bu Bu H H D-3 Et Et H H D-4 H H H H D-5 Ph Ph H H D-6 C.sub.6H.sub.13 C.sub.6H.sub.13 OCH.sub.3 OCH.sub.3 D-7 Bu Bu OCH.sub.3 OCH.sub.3 D-8 Et Et OCH.sub.3 OCH.sub.3 D-9 H H OCH.sub.3 OCH.sub.3 D-10 Ph Ph OCH.sub.3 OCH.sub.3 D-11 C.sub.6H.sub.13 C.sub.6H.sub.13 SCH.sub.3 SCH.sub.3 D-12 Bu Bu SCH.sub.3 SCH.sub.3 D-13 Et Et SCH.sub.3 SCH.sub.3 D-14 H H SCH.sub.3 SCH.sub.3 D-15 Ph Ph SCH.sub.3 SCH.sub.3 D-16 C.sub.6H.sub.13 C.sub.6H.sub.13 SCH.sub.3 SCH.sub.3 D-17 C.sub.6H.sub.13 C.sub.6H.sub.13 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 D-18 Bu Bu N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 D-19 Et Et N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 D-20 H H N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 D-21 Ph Ph N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 D-22 C.sub.6H.sub.13 C.sub.6H.sub.13 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 D-23 Bu Bu N(CH.sub.3).sub.2 N(CH.sub.3).sub.2
Compounds E-1 to E-35 can be obtained in a manner analogous to Example 6.

##STR00123##

TABLE-US-00006 Cpd. Y.sup.3 X.sup.3 E-1 H H E-2 H H E-3 H H E-4 H H E-5 H H E-6 OCH.sub.3 OCH.sub.3 E-7 OCH.sub.3 OCH.sub.3 E-8 OCH.sub.3 OCH.sub.3 E-9 OCH.sub.3 OCH.sub.3 E-10 OCH.sub.3 OCH.sub.3 E-11 OCH.sub.3 H E-12 OCH.sub.3 H E-13 OCH.sub.3 H E-14 OCH.sub.3 H E-15 OCH.sub.3 H E-16 SCH.sub.3 SCH.sub.3 E-17 SCH.sub.3 SCH.sub.3 E-18 SCH.sub.3 SCH.sub.3 E-19 SCH.sub.3 SCH.sub.3 E-20 SCH.sub.3 SCH.sub.3 E-21 SCH.sub.3 H E-22 SCH.sub.3 H E-23 SCH.sub.3 H E-24 SCH.sub.3 H E-25 SCH.sub.3 H E-26 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 E-27 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 E-28 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 E-29 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 E-30 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 E-31 N(CH.sub.3).sub.2 H E-32 N(CH.sub.3).sub.2 H E-33 N(CH.sub.3).sub.2 H E-34 N(CH.sub.3).sub.2 H E-35 N(CH.sub.3).sub.2 H

[0125] Compounds F-1 to F-35 can be obtained in a manner analogous to Example 6.

##STR00124##

TABLE-US-00007 Cpd. R.sup.101 R.sup.102 Y.sup.3 X.sup.3 F-1 C.sub.6H.sub.13 C.sub.6H.sub.13 H H F-2 Bu Bu H H F-3 Et Et H H F-4 H H H H F-5 Ph Ph H H F-6 C.sub.6H.sub.13 C.sub.6H.sub.13 OCH.sub.3 OCH.sub.3 F-7 Bu Bu OCH.sub.3 OCH.sub.3 F-8 Et Et OCH.sub.3 OCH.sub.3 F-9 H H OCH.sub.3 OCH.sub.3 F-10 Ph Ph OCH.sub.3 OCH.sub.3 F-11 C.sub.6H.sub.13 C.sub.6H.sub.13 OCH.sub.3 H F-12 Bu Bu OCH.sub.3 H F-13 Et Et OCH.sub.3 H F-14 H H OCH.sub.3 H F-15 Ph Ph OCH.sub.3 H F-16 C.sub.6H.sub.13 C.sub.6H.sub.13 SCH.sub.3 SCH.sub.3 F-17 Bu Bu SCH.sub.3 SCH.sub.3 F-18 Et Et SCH.sub.3 SCH.sub.3 F-19 H H SCH.sub.3 SCH.sub.3 F-20 Ph Ph SCH.sub.3 SCH.sub.3 F-21 C.sub.6H.sub.13 C.sub.6H.sub.13 SCH.sub.3 H F-22 Bu Bu SCH.sub.3 H F-23 Et Et SCH.sub.3 H F-24 H H SCH.sub.3 H F-25 Ph Ph SCH.sub.3 H F-26 C.sub.6H.sub.13 C.sub.6H.sub.13 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 F-27 Bu Bu N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 F-28 Et Et N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 F-29 H H N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 F-30 Ph Ph N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 F-31 C.sub.6H.sub.13 C.sub.6H.sub.13 N(CH.sub.3).sub.2 H F-32 Bu Bu N(CH.sub.3).sub.2 H F-33 Et Et N(CH.sub.3).sub.2 H F-34 H H N(CH.sub.3).sub.2 H F-35 Ph Ph N(CH.sub.3).sub.2 H

Example 7 (G-1)

[0126] ##STR00125##

[0127] To 14.6 g (0.100 mol) of tetralone and 15.0 g (1.10 mol) p-methoxy-benzaldehyd in 100 ml absolute methanol 660 mg potassium hydroxide are added. The reaction mixture is refluxed for 18 h under argon and then cooled to 25° C. The formed product is filtered off and washed with methanol. To 6.61 g (25.0 mmol) of said product in 50 ml water free ethanol 1.96 g (12.5 mmol) benzamidine hydrochloride are added. A solution of 1.65 g (25.0 mmol) potassium hydroxide in 50 ml water free ethanol is added during 15 min. Dry air is bubbled through the reaction mixture. The reaction mixture is refluxed for 24 h and then poured into water. The water phase is extracted with dichloromethane. The organic phase is dried with magnesium sulfate, the solvent is removed by distillation and the remaining residue is purified by column chromatography (toluene/hexane 1/1). The product G-1 having a melting point of 169° C. is obtained.

Example 8 (H-1)

[0128] ##STR00126##

a) 24.9 g (0.134 mol) 4-bromo-benzaldehyde and 26.8 g 4-bromo-acetophenone (0.134 mol) are dissolved under argon in 120 ml methanol. To this solution 0.270 g sodium hydroxide are added. The reaction mixture is stirred for 5 h. The formed yellow product is filtered off and is washed with water and then methanol. The product is dried in a vacuum oven (yield: 44.2 g (90%), melting point: 183-184° C.).

##STR00127##

b) To 5.00 g (13.7 mmol) of 1,3-bis-(4-bromophenyl)-2-propen-1-one (1) in 25 ml water free ethanol 1.61 g (6.83 mmol) 4-bromo-benzamidine hydrochloride are added under argon. A solution of 0.90 g (16.1 mmol) potassium hydroxide in 25 ml water free ethanol is added during 15 min. Dry air is bubbled through the reaction mixture. The reaction mixture is refluxed for 24 h and then poured into water. The product is filtered off, washed with ethanol and dried in a vacuum oven (melting point: 321-322° C.).

##STR00128##

c) To 1.00 g (1.83 mmol) of tris-2,4,6-(4-bromo-phenyl)-pyrimidine and 1.27 g (6.42 mmol) of 4-biphenylboronic acid in 20 ml toluene 5.27 g (16.19 mmol) CsCO.sub.3 in 3 ml water are added under argon. Approximately 10 mg of the Pd catalyst (WO 99/47474) are added and then the reaction mixture is refluxed for 5 h. The product is filtered off, washed with water and acetone. The product is dissolved in dichloromethane and filtered on silica gel. The solvent is removed in vacuum. The obtained product has a melting point of 364-367° C.

Example 9 (H-2)

[0129] ##STR00129##

a) The product (melting point: 204-205° C.) is prepared according to the procedure given in example 8b).

##STR00130##

b) The product (melting point: 343-345° C.) is prepared according to the procedure given in example 8c).

Example 10 (H-3)

[0130] ##STR00131##

a) The product (melting point: 207-208° C.) is prepared according to the procedure given in example 8b).

##STR00132##

b) The product (melting point: 364-367° C.) is prepared according to the procedure given in example 8c).

Example 11 (H-4)

[0131] ##STR00133##

a) The product (melting point: 145-146° C.) is prepared according to the procedure given in example 8b) (yield: 86%).

##STR00134##

b) The product (melting point: 160° C.) is prepared according to the procedure given in example 8b) (yield: 72%).

##STR00135##

c) The product (melting point: 213-214° C.) is prepared according to the procedure given in example 8c) (yield: 53%).

Example 12 (H-5)

[0132] ##STR00136##

a) The product (melting point: 122-123° C.) is prepared according to the procedure given in example 8b) (yield: 91%).

##STR00137##

b) The product (melting point: 152-153° C.) is prepared according to the procedure given in example 8b) (yield: 54%).

##STR00138##

c) The product (melting point: 220-221° C.) is prepared according to the procedure given in example 8c) (yield: 80%).

Example 13 (H-6)

[0133] ##STR00139##

a) The product (melting point: 245-246° C.) is prepared according to the procedure given in example 8b) (yield: 42%).

##STR00140##

b) The product (melting point: 333-334° C.) is prepared according to the procedure given in example 8c) (yield: 75%).

Example 14 (H-7)

[0134] ##STR00141##

a) The product (melting point: 204-205° C.) is prepared according to the procedure given in example 8b) (yield: 46%).

##STR00142##

b) The product (melting point: 329-331° C.) is prepared according to the procedure given in example 8c) (yield: 61%).

Example 15

[0135] ##STR00143##

[0136] To 264 mg (1.0 mmol) of the pyrimidine (see scheme above) in 20 ml chloroform 454 mg (2.0 mmol) DDQ are added. The reaction mixture is refluxed for 1 day. Additional 908 mg (4.0 mmol) of DDQ are added and the reaction mixture is refluxed for additional 2 days. The reaction mixture is filtered on silica gel with dichloromethane. A column chromatography on silica gel with toluene gives the desired product in 61% yield (mp. 163-165° C.).

Example 16 (J-1)

[0137] ##STR00144##

a) 10.0 g (57.2 mol) 3,4-dimethoxy-benzaldehyde and 10.3 g (57.2 mol) 3,4-dimethoxy-acetophenone are dissolved under argon in 50 ml methanol. To this solution 0.34 g sodium hydroxide are added. The reaction mixture is stirred for 22 h at 40° C. The reaction mixture is cooled to 0° C. and the precipitated product is filtered off. The product is dried in vacuum (yield: 18.2 g (97%), melting point: 108-110° C.).

##STR00145##

b) To 7.00 g (21.3 mmol) of 1,3-bis-(3,4-dimethoxy-phenyl)-2-propen-1-one (1) in 40 ml water free ethanol 1.67 g (10.7 mmol) benzamidine hydrochloride are added under argon. A solution of 1.41 g (25.1 mmol) potassium hydroxide (85%) in 40 ml water free ethanol is added during 20 min. Dry air is bubbled through the reaction mixture. The reaction mixture is refluxed for 48 h and then poured into water. The product is filtered off and washed with ethanol. A column chromatography on silica gel with toluene gives the desired product J-1 (melting point: 157-158° C.).

Example 17 (J-2)

[0138] ##STR00146##

a) 10.0 g (57.2 mol) 2,4-dimethoxy-benzaldehyde and 10.3 g 2,4-dimethoxy-acetophenone (57.2 mol) are dissolved under argon in 50 ml methanol. To this solution 0.34 g sodium hydroxide are added. The reaction mixture is stirred for 48 h at 40° C. The reaction mixture is diluted with water and the precipitated product is filtered off. The product is washed with water and dried in vacuum (melting point: 127-129° C.).

##STR00147##

b) To 6.60 g (20.1 mmol) of 1,3-bis-(2,4-dimethoxy-phenyl)-2-propen-1-one (1) in 40 ml water free ethanol 2.34 g (10.1 mmol) biphnenyl-benzamidine hydrochloride are added under argon. A solution of 1.41 g (25.1 mmol) potassium hydroxide (85%) in 40 ml water free ethanol is added during 15 min. Dry air is bubbled through the reaction mixture. The reaction mixture is refluxed for 48 h and then poured into water. The water phase is extracted with dichloromethane. The organic phase is dried with MgSO.sub.4 and the solvent is removed in vacuum. A column chromatography on silica gel with toluene/hexane 3/2 give the desired product J-2 (melting point: 165-167° C.).

Example 18 (J-4)

[0139] ##STR00148##

[0140] To 5.50 g (15.2 mmol) of 1,3-bis-(2,4-dimethoxy-phenyl)-2-propen-1-one (1) in 30 ml water free ethanol 0.87 g (9.14 mmol) guanidine hydrochloride are added under argon. A solution of 1.21 g (21.5 mmol) potassium hydroxide (85%) in 30 ml water free ethanol is added during 15 min. Dry air is bubbled through the reaction mixture. The reaction mixture is refluxed for 48 h and then poured into water. The water phase is extracted with dichloromethane. The organic phase is dried with MgSO.sub.4 and the solvent is removed in vacuum. A column chromatography on silica gel with dichloromethane/ethyl acetate 2/1 gives the desired product (melting point: 211-213° C.).

Example 19 (J-5)

[0141] ##STR00149##

a) To a suspension of 0.69 g sodium hydride in 25 ml terahydrofurane (THF) 5.38 g (27.4 mmol) 4-acetyl-biphenyl are added at 0° C. under argon. After 1 h 5.00 g (27.4 mmol) 4-bihenylcarbadehyde in 25 ml THF are added. The reaction mixture is stirred for 19 h at 25° C. The formed precipitate is filtered off and washed with THF. The product is refluxed for 1 h in 100 ml iso-propanol and 30 ml water. The product is filtered off and dried in vacuum.

##STR00150##

b) The desired product J-5 (melting point: 245-246° C.) is prepared according to the procedure given in example 17b).

Example 20 (J-6)

[0142] ##STR00151##

[0143] The product J-6 (melting point: 243-246° C.) is prepared according to the procedure given in example 17b).

Example 21 (J-7)

[0144] ##STR00152##

a) 18.3 g (0.100 mol) 2,4-dimethoxy-benzaldehyde and 12.1 g (0.100 mol) 3-acethyl pyridine are dissolved under argon in 100 ml methanol. To this solution 0.66 g sodium hydroxide are added. The reaction mixture is refluxed for 18 h. The reaction mixture is poured into water and extracted with dichloromethane. The organic phase is dried with MgSO.sub.4 and the solvent is removed in vacuum. A column chromatography on silica gel with toluene/ethyl acetate 2/1 give the desired product (yield: 7.3 g (27%)).

##STR00153##

b) The product J-7 (melting point: 136° C.) is prepared according to the procedure given in example 17b).

Example 22 (K-1)

[0145] ##STR00154##

a) To 10.0 g (27.3 mmol) of 1,3-bis-(4-bromophenyl)-2-propen-1-one in 70 ml ethanol 2.14 g (13.7 mmol) benzamidine hydrochloride are added under argon. A solution of 1.80 g (32.1 mmol) potassium hydroxide (85%) in 50 ml ethanol is added during 15 min. Dry air is bubbled through the reaction mixture. The reaction mixture is refluxed for 24 h and then is poured into water. The product is filtered off, washed with water and 10% tartaric acid, crystallized from glacial acetic acid and washed with ethanol (yield: 9.2 g (58%); melting point: 203-205° C.).

##STR00155##

b) To 4.45 g (9.55 mmol) 4,6-tris-(p-bromophenyl)-2-phenyl-pyrimidine in 200 ml toluene 2.99 g (19.1 mmol) 4-chloro-phenylboronic acid are added. The suspension is refluxed under argon. Argon is passed through the reaction mixture. 9.33 g (28.6 mmol) of caesium carbonate in 6 ml water are added dropwise to the reaction mixture. Then 0.40 g of the catalyst are added. The reaction mixture is refluxed for 16 h and then the solids are filtered off. The solvent is removed in vacuum. The residue is dissolved in dichloromethane and is washed with water. The organic phase is dried with magnesium sulfate. The solvent is removed in vacuum. The product is crystallized from 100 ml ethanol (yield: 99%; melting point: 258-259° C.).

##STR00156##

c) To 1.00 g (1.89 mmol) 4,6-bis-(p-bromophenyl)-2-phenyl-pyrimidine in 45 ml toluene 287 mg (1.89 mmol) 4-metoxy-biphenylboronic acid are added. Argon is passed through the reaction mixture. 1.23 g (3.78 mmol) of caesium carbonate in 6 ml water is added dropwise to the reaction mixture. Then 20 mg of the catalyst is added. The reaction mixture is refluxed for 18 h. Additional 4-methoxy-biphenylboronic acid and caesium carbonate is added in a 1 to 1 molar ratio until the reaction is complete. The product is filtered off and is washed with ethanol, water and again ethanol. The product is dissolved in boiling DMF, filtered on super gel (Fluka 56678, CAS [91053-39-3]) and crystallized (yield: 0.90 g (71%); melting point: 345-348° C.).

[0146] In a manner analogous to Example 22 Compounds K-2 to K-15 are obtained.

##STR00157##

TABLE-US-00008 Cpd. Ar K-1 [00158] K-2 [00159] K-3 [00160] K-4 [00161] K-5 [00162] K-6 [00163] K-7 [00164] K-8 [00165] K-9 [00166] K-10 [00167] K-11 [00168] K-12 [00169] K-13 [00170] K-14 [00171] K-15 [00172] K-16 [00173]

Example 23 (L-1)

[0147] ##STR00174##

a) The product is prepared according to the procedure given in example 22a).

##STR00175##

b) The product is prepared according to the procedure given in example 22b).

##STR00176##

c) The product is prepared according to the procedure given in example 22c).

[0148] In a manner analogous to Example 23 Compounds L-2 to L-15 are obtained.

##STR00177##

TABLE-US-00009 Cpd. Ar L-1 [00178] L-2 [00179] L-3 [00180] L-4 [00181] L-5 [00182] L-6 [00183] L-7 [00184] L-8 [00185] L-9 [00186] L-10 [00187] L-11 [00188] L-12 [00189] L-13 [00190] L-14 [00191] L-15 [00192] L-16.sup.1) [00193] .sup.1)A 100 nm thin film of Compound L-16 showed good film quality and strong photoluminescence at 430 nm (λ.sub.max).

Example 24 (M-1)

[0149] ##STR00194##

a) The product is prepared according to the procedure given in example 22b).

##STR00195##

b) The product is prepared according to the procedure given in example 22c).

[0150] In a manner analogous to Example 24 Compounds M-2 to M-15 are obtained.

##STR00196##

TABLE-US-00010 Cpd. Ar M-1 [00197] M-2 [00198] M-3 [00199] M-4 [00200] M-5 [00201] M-6 [00202] M-7 [00203] M-8 [00204] M-9 [00205] M-10 [00206] M-11 [00207] M-12 [00208] M-13 [00209] M-14 [00210] M-15 [00211] M-16 [00212]

Example 25 (N-1)

[0151] ##STR00213##

[0152] 1.0 g (1.83 mmol) 2,4,6-tris-(p-bromophenyl)-pyrimidine, 1.49 g (8.26 mmol) 1,1-diphenylethylen, 40 mg Palladium-(II)-acetate, 150 mg (1.47 mmol) dimethylglycine, 1.39 g (16.5 mmol) sodium hydrogen carbonate and 70 mg (0.46 mmol) FeCl.sub.3 are dissolved in 8 ml N-methyl-pyrrolidone. The reaction mixture is heated for 48 h at 150° C. The reaction mixture is poured into water and 20% hydrochloric acid is added. The water phase is extracted with dichloromethane. The organic phase is dried with magnesium sulfate. The solvent is distilled off. A column chromatography (silica gel, toluene/hexane 1/3) result in the desired product (119.5-120.5° C.).

Example 26

[0153] ##STR00214##

[0154] The product is synthesized as described in Example 31 of CH-A-542212.

Application Example 1

[0155] Present compounds A1, A2, A3, B1, B2, C1, G1 and H1 as light emitting materials, respectively, 2,5-bis(1-naphthyl)-1,3,4-oxadiazole and a polycarbonate resin in a weight ratio of 5:3:2 are dissolved in tetrahydrofuran, and the solution is spin-coated on a cleaned glass substrate with an ITO electrode to form a light-emitting layer having a thickness of 100 nm. An electrode having a thickness of 150 nm is formed thereon from a magnesium/indium alloy having a magnesium/indium mixing ratio of 10/1, to obtain an organic EL device. The device exhibits light emission with excellent brightness and efficiency at a direct current voltage of 5 V.

Application Example 2

[0156] Compounds A1, A2, A3, B1, B2, C1, G1 and H1, respectively, are vacuum-deposited on a cleaned glass substrate with an ITO electrode to form a light-emitting layer having a thickness of 100 nm. An electrode having a thickness of 100 nm is formed thereon from a magnesium/silver alloy having a magnesium/silver mixing ratio of 10/1, to obtain an organic EL device. The light-emitting layer is formed by deposition under a vacuum of 10.sup.6 Torr at a substrate temperature of room temperature. The device shows emission having an excellent brightness and efficiency at a direct current voltage of 5 V.

Application Example 3

[0157] Compounds A1, A2, A3, B1, B2, C1, G1 and H1, respectively, are dissolved in methylene chloride tetrahydrofuran, and the solution is spin-coated on a cleaned glass substrate with an ITO electrode to form a light-emitting layer having a thickness of 50 nm. Then, aluminum bis(2-methyl-8-quinolinate)(2-naphtolate) is vacuum-deposited to form an electron-injecting layer having a thickness of 10 nm, and an electrode having a thickness of 100 nm is formed thereon from a magnesium/aluminum alloy having a magnesium/aluminum mixing ratio of 10/1, to obtain an organic EL device. The light-emitting layer and the electron-injecting layer are formed by deposition under a vacuum of 10.sup.6 Torr at a substrate temperature of room temperature. The device shows an emission having an excellent brightness and efficiency at a direct current voltage of 5 V.

Application Example 4

[0158] Compounds A1, A2, A3, B1, B2, C1, G1 and H1, respectively, are vacuum-deposited on a cleaned glass substrate with an ITO electrode to form a light-emitting layer having a thickness of 50 nm. Then, aluminum tris(8-hydroxyquinolinate) is vacuum-deposited to form an electron-injecting layer having a thickness of 10 nm and an electrode having a thickness of 100 nm is formed thereon from an aluminum/lithium alloy having an aluminum/lithium mixing ratio of 50/1, to obtain an organic EL device. A hole-injecting layer and the light-emitting layer are formed by deposition under a vacuum of 10.sup.6 Torr at a substrate temperature of room temperature. The device shows a light emission having an excellent brightness and efficiency at a direct current voltage of 5 V.

Application Example 5

[0159] One of hole-injecting materials (H-1) to (H-6) is vacuum-deposited on a cleaned glass substrate with an ITO electrode, to form a hole-injecting layer having a thickness of 30 nm. Then, one of light-emitting materials A1, A2, A3, B1, B2, C1, G1 and H1, respectively is vacuum-deposited to form a light-emitting layer having a thickness of 30 nm. Further, one of electron-injecting materials (E-1) to (E-6) is vacuum-deposited to form an electron-injecting layer having a thickness of 30 nm. An electrode having a thickness of 150 nm is formed thereon from a magnesium/silver alloy having a magnesium/silver mixing ratio of 10/1, to obtain an organic EL device. Each layer is formed under a vacuum of 10.sup.6 Torr at a substrate temperature of room temperature. All the organic EL devices obtained in these Examples shows high brightness and efficiency.

##STR00215## ##STR00216##

Application Example 6

[0160] On a cleaned glass substrate with an ITO electrode, 4,4′,4″-tris(N-(3-methylphenyl)-N-phenylamino)triphenylamine is vacuum-deposited to form a first hole-injecting layer having a thickness of 25 nm. Further, a hole-injecting material (H-1) is vacuum-deposited to form a second hole-injecting layer having a thickness of 5 nm. Then, compounds A1, A2, A3, B1, B2, C1, G1 and H1, respectively, as light-emitting materials are vacuum-deposited to form a light-emitting layer having a thickness of 20 nm. Further, an electron-injecting material (E-1) is vacuum-deposited to form an electron-injecting layer having a thickness of 30 nm. Then, an electrode having a thickness of 150 nm is formed thereon from a magnesium/silver alloy having an magnesium/silver mixing ratio of 10/1, to obtain an organic EL device. The device shows emission having an outstanding brightness and efficiency at a direct current voltage of 5 V.

Application Example 7

[0161] On a cleaned glass substrate with an ITO electrode, 4,4′,4″-tris(N-(1-naphthyl)-N-phenylamino)triphenylamine is vacuum-deposited to form a first hole-injecting layer having a thickness of 25 nm. Further, a hole-injecting material (H-2) is vacuum-deposited to form a second hole-injecting layer having a thickness of 5 nm. Then, compounds A1, A2, A3, B1, B2, C1, G1 and H1, respectively, as light-emitting materials are vacuum-deposited to form a light-emitting layer having a thickness of 20 nm. Further, an electron-injecting material (E-5) is vacuum-deposited to form an electron-injecting layer having a thickness of 30 nm. Then, an electrode having a thickness of 150 nm is formed thereon from a magnesium/silver alloy having an magnesium/silver mixing ratio of 10/1, to obtain an organic EL device. The device shows an emission having a outstanding brightness and efficiency at a direct current voltage of 5V.

Application Example 8

[0162] A hole-injecting material (H-5) is vacuum-deposited on a cleaned glass substrate with an ITO electrode to form a hole-injecting layer having a thickness of 20 nm. Then, compounds A1, A2, A3, B1, B2, C1, G1 and H1, respectively, as light-emitting materials are vacuum-deposited to form a light-emitting layer having a thickness of 20 nm. Further, an electron-injecting material (E-2) is vacuum-deposited to form a first electron-injecting layer having a thickness of 20 nm. Then, an electron-injecting material (E-5) is vacuum-deposited to form a second electron-injecting layer having a thickness of 10 nm, and an electrode having a thickness of 150 nm is formed thereon from a magnesium/silver alloy having an magnesium/silver mixing ratio of 10/1, to obtain an organic EL device. The device shows light emission having an excellent brightness and efficiency at a direct current voltage of 5 V.

Application Example 9

[0163] An organic EL device is prepared in the same manner as in Example 5 except that the light-emitting layer is replaced with a 30 nm thick light-emitting layer formed by vacuum-depositing compounds A1, A2, A3, B1, B2, C1, G1 and H1, respectively, and one of the dopant compounds (D-1) to (D-7) in a weight ratio of 100:1. All the organic EL devices obtained in these Examples shows high brightness characteristics and gives intended light emission colors.

##STR00217##

Application Example 10

[0164] An organic EL device is prepared in the same manner as in Example 5 except that the light-emitting layer is replaced with a 30 nm thick light-emitting layer formed by vacuum-depositing compounds A1, A2, A3, B1, B2, C1, G1 and H1, respectively and one of Compounds (D-1) to (D-7) in a weight ratio of 100:1. All the organic EL devices obtained in these Examples shows high brightness characteristics, or a maximum brightness and gives intended light emission colors.

Application Example 11

[0165] A hole-injecting material (H-2) is vacuum-deposited on a cleaned glass substrate with an ITO electrode to form a hole-injecting layer having a thickness of 30 nm. Then, 4,4′-bis(α,α-diphenylvinyl)biphenyl and a light-emitting material selected from compounds A1, A2, A3, B1, B2, C1, G1 and H1 for a light-emitting layer are vacuum-deposited in a weight ratio of 100:5 to form a light-emitting layer having a thickness of 30 nm. Further, an electron-injecting material (E-3) is vacuum-deposited to form an electron-injecting layer having a thickness of 30 nm. Then, an electrode having a thickness of 150 nm is formed thereon from a magnesium/silver alloy having an magnesium/silver mixing ratio of 10/1, to obtain an organic EL device. The device shows an emission having an outstanding brightness and efficiency at a direct current voltage of 5 V.

Application Example 12

[0166] An organic EL device is prepared in the same manner as in Example 11 except that the light-emitting layer is replaced with a 30 nm thick light-emitting layer formed by vacuum-depositing aluminum tris(8-hydroxyquinolinate) and one of the light-emitting materials A1, A2, A3, B1, B2, C1, G1 and H1 in a weight ratio of 100:3. All the organic EL devices obtained in these Examples shows high brightness characteristics at a direct current of 5 V.

[0167] The organic EL devices obtained in the Application Examples of the present invention show an excellent light emission brightness and achieved a high light emission efficiency. When the organic EL devices obtained in the above Examples are allowed to continuously emit light at 3 (mA/cm.sup.2), all the organic EL devices remain stable. Since the light-emitting materials of the present invention have a very high fluorescence quantum efficiency, the organic EL devices using the light-emitting materials achieved light emission with a high brightness in a low electric current applied region, and when the light-emitting layer additionally uses a doping material, the organic EL devices are improved in maximum light emission brightness and maximum light emission efficiency. Further, by adding a doping material having a different fluorescent color to the light-emitting material of the present invention, there are obtained light-emitting devices having a different light emission color. The organic EL devices of the present invention accomplish improvements in light emission efficiency and light emission brightness and a longer device life, and does not impose any limitations on a light-emitting material, a dopant, a hole-injecting material, an electron-injecting material, a sensitizer, a resin and an electrode material used in combination and the method of producing the device. The organic EL device using the material of the present invention as a light-emitting material achieves light emission having a high brightness with a high light emission efficiency and a longer life as compared with conventional devices. According to the light-emitting material of the present invention and the organic EL device of the present invention, there can be achieved an organic EL device having a high brightness, a high light emission efficiency and a long life.